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Holiday Rentals near Wine Cheese & More

4103 Main St, Chincoteague Island, Virginia 23336-2411
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    Travellers to Chincoteague Island are booking April dates now. Secure your holiday rental today, and have the perfect trip.
    All 100 Rentals in Chincoteague Island
    Waterfront, 5 BR, 4 BA, Elevator, sleeps 101 / 48
    (1)Excellent
    0.8 kilometres from Wine Cheese & More
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Beautiful Chincoteague Island retreat1 / 15
    (17)Very good
    0.5 kilometres from Wine Cheese & More
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Duck's Delight - Your Seaside Home Away From Home!1 / 19
    (46)Excellent
    0.4 kilometres from Wine Cheese & More
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Cozy cottage near Old town Fishing Village1 / 12
    (2)Very good
    0.5 kilometres from Wine Cheese & More
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Private Garden
    • Washer
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 August 2016
    Good:- Clean, comfortable and functional- Location walkable to Main St shops and a bowling alley- Window air conditioners worked wellCould be improved:- Owner's...
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    About this property
    Cute, colorful 2 bedroom cottage with front and back porches. Walking distance to charming old town Main Street shops and restaurants. Back yard with grill and picnic table. Outside shower. Have coffee on the sunny back porch overlooking private back yard. Lots of windows. Wifi. DVDs for...
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    Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Tranquil Shores - Relaxation With a Water View1 / 30
    (11)Excellent
    1.5 kilometres from Wine Cheese & More
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Grill
    • Waterfront
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 July 2018
    Wow! Exceptionally close (walking distance) to both Assateague National Wildlife Refuge AND family friendly activities, such as bike shops and eateries. Very quiet...
    Reviewed 19 July 2018
    Communication with the owner was great. The house was in a convenient location near downtown on a very quiet street. The kids were able to ride their bikes there safely. We...
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    About this property
    Peaceful 3 bedroom/2 bathroom home located directly on Eel Creek. Appreciate the natural beauty of Chincoteague Island with gorgeous nature views from both the lower level screened in porch as well as the balcony off of the master suite. Enjoy relaxing mornings with the sunrise and breeze filled...
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    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Spacious, historic Chincoteague Is. vacation house1 / 13
    (12)Very good
    1.4 kilometres from Wine Cheese & More
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed 12 August 2018
    The home was cozy, spacious and well equipped with anything we might need for the week-including a stroller, pack-n-play, beach toys, books, games, Barbie dolls and movies. In...
    Reviewed 11 June 2018
    This place was amazing. Spacious well kept house. Our own private drive. Close enough to stuff so we could get there quickly but not right in the middle of it all. We loved the...
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    About this property
    Totally updated but traditional 'home away from home' facing the Chincoteague Channel on Chincoteague Island, minutes from the quaint downtown and the Assateague National Seashore and Wildlife refuge. Relax in this spacious, clean, and beautifully furnished home with water views of the sunset from...
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    Chincoteague Island, Virginia
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sunset Bay Villas - Another Day in Paradise1 / 33
    (10)Excellent
    0.5 kilometres from Wine Cheese & More
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Washer
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    The location of this condo is amazing. You have gorgeous views of the bay from the living room - dinning room area and the master bedroom. The sunsets were amazing. We liked...
    Reviewed 2 April 2018
    Annie was so helpful & always prompt with answering any questions I had. The condo was very clean, spacious & suited our needs perfectly! The location is awesome being...
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    About this property
    ANOTHER DAY IN PARADISE CHINCOTEAGUE BEAUTIFUL BAY FRONT CONDO WITH AMAZING WATER VIEWS Owner operated by: Annie Switzer Call 240/498/0074 *** Booking Fall 2018 & Beyond *** PLEASE CONTACT ME BEFORE BOOKING SUMMER 2019 Unit 103 - 'Another Day in Paradise' Unit 213 - 'Sunset in Paradise' 2nd...
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    Chincoteague Island, Virginia
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sunset Bay Villas Chincoteague Island - Sunset in Paradise1 / 24
    (8)Excellent
    0.4 kilometres from Wine Cheese & More
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 July 2018
    This property was perfect for our family (family of 4 plus 2 grandparents). Annie was a pleasure to work with right from the beginning. Payment schedule was reasonable and...
    Reviewed 27 February 2018
    We stayed in Sunset in Paradise for a week a few years ago and absolutely loved it (and rented again for summer 2018)! The owners are very responsive, hospitable, and helpful in...
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    About this property
    ANOTHER DAY IN PARADISE CHINCOTEAGUE BEAUTIFUL BAY FRONT CONDO WITH AMAZING WATER VIEWS Owner operated by: Annie Switzer Call 240/498/0074 *** Booking Fall 2018 *** PLEASE CONTACT OWNER BEFORE BOOKING SUMMER 2019 Unit 213 - 'Sunset in Paradise' at Sunset Bay Villas *** Please see FKN 7097918...
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    Location Information
    Chincoteague Island, Virginia
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Key West Cottages1 / 4
    (9)Very good
    0.3 kilometres from Wine Cheese & More
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Patio
    • Balcony
    • Hot Tub
    • Air Conditioning
    • Parking
    • Shared Indoor Pool
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Was a beautiful place to stay. Made for two. Bed was comfortable. Living room couch should be one that reclines back. Was uncomfortable sittingStraight and looking at a tv...
    Reviewed 4 August 2018
    Key West Cottages Chincoteague was the perfect little getaway. The cottage was clean. The grounds were well kept.. Expect we will rent here again.
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    About this property
    Beautiful cottages located in the heart of Downtown Chincoteague with views of the Chincoteague Channel and Bay. The Key West Cottages are equipped with full kitchens, cozy living rooms, Queen bedrooms and large tiled showers. Amenities such as an indoor pool, hot tub and outdoor pool next door...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    0.9 kilometres from Wine Cheese & More
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    NEW for 2017. This beautiful Victorian is located on Main Street and just a short walk to town. The 4BR home is spacious and very charming with much of it's original integrity still in place. Amenities include central heat & air, all appliances including washer/dryer, outside hot & cold shower,...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    0.4 kilometres from Wine Cheese & More
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    As one of our newest vacation rental listings, we're pleased to be able to offer you 'A Sunshine Cottage'! With all the charm of a Chincoteague-style cottage, you'll be reminded of the days gone by. The front porch is the perfect spot to relax with a cool drink and book, and the convenient in-town...
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    Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Agape House1 / 15
    (1)Excellent
    0.7 kilometres from Wine Cheese & More
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Wi-Fi
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 June 2016
    We have been vacationing on Chincoteague for years and Love everything about it, This is a great house with lots of room we had two adults and four teens and it worked out...
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    About this property
    A great three bedroom home with a convenient in town location - just a short distance to Maddox Blvd. and Main St. for dining, shopping, etc. The master suite has a queen bed and private bathroom with TV. The second bedroom offers two queen beds and lots of extra space. Through the open dining and...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    On Island Time1 / 20
    (1)Excellent
    0.5 kilometres from Wine Cheese & More
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 March 2017
    We have been coming to Chincoteague Island since 1988 and this is the best house we have been to. The décor is sweet and thoughtful. All the little touches are lovely and the...
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    About this property
    Wow... What a show piece! 'On Island Time' is exactly what you expect in your beach home, from the bright and fun decor to the spacious and bright floor plans, all of this wrapped in a traditional Eastern Shore Home. The front enclosed porch is great for reading or just relaxing in the afternoon...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Captain's Loft1 / 22
    (3)Very good
    1.1 kilometres from Wine Cheese & More
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 September 2017
    Been coming to Chincoteague for years and have stayed all over the island. Hands down this is my favorite place. Clean, plenty of Bedrooms and Bathrooms. It also does have a...
    Reviewed 13 October 2015
    This two-floor unit offered peace and quiet. The quality and amenities were good and more room than we expected. The three bedrooms downstairs included three full baths...
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    About this property
    Captain's Loft has NEW OWNERS! This vacation home is located just a short walk to Maddox Blvd! Close to everything, but situated perfectly for a quiet and relaxing stay. This duplex home features three bedrooms downstairs, and two of those bedrooms have full baths. There's another full bath...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Paradise1 / 28
    (1)Excellent
    1.1 kilometres from Wine Cheese & More
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2017
    Beautiful stunning and breath taking ! The view was beautiful. House was clean upon arrival, very spacious! Loved the kitchen. The bedrooms were very clean and spacious! Loved...
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    About this property
    If you're looking for that special vacation home that offers everything you'll need, look no further. Paradise offers all top-of-the-line amenities including cherry wood floors, chef's kitchen and spacious master bedroom suite with custom bathroom and Jacuzzi tub. The main floor features a bright,...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Anchor's Rest1 / 24
    (1)Excellent
    0.6 kilometres from Wine Cheese & More
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 July 2018
    This was the perfect beach house for our family of 5 plus our mastiff mix. This home is close to downtown and walking distance to shops. A nice walk each evening to the Island...
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    Anchor’s Rest—Centrally located, just a short walk to the carnival grounds, shopping, ice cream, dinner and the movies. This welcoming, spacious rental home features a fully equipped kitchen (don’t forget to bring k-cups!) with abundant counter space opening into the separate dining room. Enjoy the...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Hill House1 / 18
    (2)Excellent
    0.4 kilometres from Wine Cheese & More
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Wi-Fi
    • Air Conditioning
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 September 2013
    My family of five stayed with our in-laws with their family of six at this beautiful home in July of this year. Right on Main Street, within walking distance of a terrific...
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    About this property
    Welcome to the 'NEW' Hill House! Wonderful traditional island home with fantastic new upgrades! The kitchen has recently been renovated, along with the bathrooms. Excellent in town location, walk to dinner, movie, shopping & galleries. Hill House features 4 bedrooms and 2.5 bathrooms, with a first...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    Donovan's Reef1 / 15
    (1)Excellent
    0.4 kilometres from Wine Cheese & More
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Wi-Fi
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 August 2014
    Just returned from one of the best vacations ever. This house was nice and big. There were 8 in our party and there was plenty of room to speed out. The kitchen was well...
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    About this property
    What a great house and it is PET FRIENDLY! Donovan's Reef is a classic home that offers large living spaces and bedrooms. On the first floor the original wood floors will guide you through a beautiful dining room (will seat 8 comfortably), right into a well appointed living room and den plus...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    1.3 kilometres from Wine Cheese & More
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Grill
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tastefully remodeled and decorated, 'Gone Coastal' is the perfect motto for this beach getaway! Located close to downtown - movies, shopping, restaurants and more. And you're only about 2 miles to the entrance to the beach! This rental features all modern amenities (central a/c & all appliances)...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Mermaid Crossing1 / 21
    (1)Excellent
    1.5 kilometres from Wine Cheese & More
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Wi-Fi
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 July 2018
    This location was an unexpected delight! More than any one particular thing, it was comfortable! We will be returning!
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    About this property
    Comfortable, pet friendly home on large, side-creek lot with fantastic views from both the front and back of house! Excellent crabbing from dock! (Property sits on creek only suitable for kayaks, canoes and crabbing.) Just a short distance to Memorial Park and Fairgrounds. 2 living room areas, 2...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Aerie (Sunset Bay 120)1 / 29
    (1)Very good
    0.4 kilometres from Wine Cheese & More
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 June 2018
    We stayed in #120 in Sunset Bay Villas. The condo was updated, beautifully decorated and clean. It was perfect for our family of 6. The location was great, right on the bay with...
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    About this property
    Come and enjoy this beautiful 3 bedroom villa! Conveniently located next to to pool, this ground-level condo allows you to walk right out from your balcony to the marina/dock. Enjoy all of the Chincoteague Island decor, spacious open floor plan, and the master bedroom suite featuring a private bath...
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    Chincoteague Island, Virginia
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Big Pines1 / 9
    (2)Excellent
    0.7 kilometres from Wine Cheese & More
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 November 2015
    Well maintained home within walking and biking distance of many shops and restaurants. Lovely screened in porch and the fire pit was an added bonus.
    Reviewed 25 September 2014
    I have went to chincoteague yearly since i was born and by far this is the first place i am going to stay for now on. Walking into this home i fell in love and instantly wanted...
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    About this property
    ***3545 Willow Street*** Very nice, comfortable 2 BR home will delight you with it's updated kitchen and new appliances. The large screened-in back porch with gas grill. Deck will accommodate outdoor entertaining. Centrally located, it is a short walk to town/shopping and the carnival grounds. 3...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Porthole1 / 20
    (1)Very good
    0.9 kilometres from Wine Cheese & More
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • DVD Player
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2018
    This is a very nice house with some Pros and Cons. Good location. Clean and modernPlenty of parking. Great Views. Large waterfront deck area. WiFi and AC reliable...
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    Porthole - Fabulous Waterfront Location featuring 180 degree waterviews of Chincoteague Bay and Marsh Island from the living room, dining room, covered deck and bonus room. Deep water slip on intercoastal waterway accommodates your boat up to 45 feet. Central air, ceiling fans in all rooms,...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    0.9 kilometres from Wine Cheese & More
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for a vacation retreat without all the fancy and frills? Look no further than this fabulous home - Holly Haven. Clean and comfortable best describes this single-story, ranch style family home. Enjoy outdoor living on the back deck or back yard. Holly Haven is conveniently located on a...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    A 'Teague of Our Own1 / 21
    (3)Excellent
    0.1 kilometres from Wine Cheese & More
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Wi-Fi
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    This pet-friendly home is a wonderfully comfortable place to spend a vacation. The owners have it furnished to satisfy many different tastes, - from those of us who like a...
    Reviewed 2 August 2018
    My family stayed here recently and had the best time! The house is comfortable and well-decorated, with great natural light, plenty of space to spread out, and lots of seating...
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    About this property
    Welcome to A 'Teague of Our Own! Formerly known as 'Stormbreak,' this in-town home is an easy walk or bike to downtown or Maddox Blvd. Nicely decorated with three bedrooms. Living room has abundant seating a flat screen TV and DVD player. Wireless internet service is provided. The enclosed porch...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Heron Creek1 / 31
    (1)Excellent
    1.2 kilometres from Wine Cheese & More
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 June 2018
    Fantastic time at Heron Creek. Couldn't ask for better. Very clean, very comfortable, perfectly situated.
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    About this property
    This beautiful creek front duplex has everything you could dream of in your vacation home. The moment you enter Heron Creek you'll be invited by the high foyer ceilings that will walk you into the spacious great room. There you'll find a beautiful upgraded kitchen with stainless appliances, granite...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sundance at Marsh Island1 / 16
    (1)Excellent
    0.2 kilometres from Wine Cheese & More
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 July 2018
    This was my 1st time visiting Chincoteague Island. I can honestly say I will be back next year. We stayed the second week of July, we had beautiful weather. If you are looking...
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    About this property
    Nestled on the tip of Marsh Island, this fabulous 2 bedroom townhome features spectacular views of the Chincoteague Bay. Watch the fishing boats go by and witness the million dollar sunsets everyone talks about - all from the comfort of your own vacation home! The open floor plan downstairs is very...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Cowboy Cottage1 / 18
    (4)Very good
    0.7 kilometres from Wine Cheese & More
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Wi-Fi
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 July 2018
    This was within walking distance of dollar general and some other shops, only a couple of miles from the beach!House was perfect!!!How was pet friendly and clean! lots of room...
    Reviewed 7 August 2017
    I found Chincoteague Island an enjoyable vacation destination. The Cowboy Cottage is a comforortable, somewhat rustic place to stay. It's central location on the island makes...
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    About this property
    Cowboy Cottage is a pet friendly home conveniently located a block from Maddox Blvd., and just a couple of blocks from downtown Main Street. This ranch-style home has an open floor plan and is handicap accessible with a ramp to enter the house and bedroom/bathroom accessibility. There is a large...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    A Second Wind1 / 21
    (1)Excellent
    1.1 kilometres from Wine Cheese & More
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 days ago
    Unfortunately we had to evacuate within 2.5 days of getting into the house. The house was absolutely beautiful with a great view. So far out of the 6yrs of coming I love the...
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    About this property
    A luxury waterfront vacation rental home with community pool privileges. Located on Chincoteague Bay, right at the water's edge. Enjoy breathtaking views and beautiful sunsets! On the first floor you'll find a sitting area (Double-size pull out sofa), two bedrooms (Queen & 2 Twins) with a common...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Shady Rest1 / 10
    (1)Excellent
    1.5 kilometres from Wine Cheese & More
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 weeks ago
    This was an absolute hidden gem! Kitchen was newly remodeled and well stocked. Made breakfast every morning and 2 dinners during our stay. Everything we needed was there. I...
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    About this property
    ***6303 Chester Park***** Well appointed home located in quiet neighborhood offers first floor bedroom and bath. Offers internet access!*** Bed Sizes: 2 Queen, 2 Sets of Bunks(1 Twin & 1 Double on each)*** Prime Season Rate: $975 weekly/$195 per night. Off Season Rates: $625 weekly/$125 per...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Poppy's House1 / 9
    (1)Excellent
    0.2 kilometres from Wine Cheese & More
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 July 2017
    This was the 4th time been to Poppy's House in Chincoteague.we stayed 10 days this time and loved every minute of it. The house had a great part in helping to make this vacation...
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    About this property
    ***6313 Cleveland Street*** Walk to everything including shopping, restaurants and entertainment from this convenient in town location! This house has been completely renovated and is a great house for your vacation! Wireless internet!*** Outside Shower is not enclosed*** Bed Sizes: 2 Queen, 2...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Island Retreat1 / 11
    (1)Excellent
    1.4 kilometres from Wine Cheese & More
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 August 2017
    I enjoyed the stay here with my husband and two daughters. the master was very nice and spacious, i loved the layout and having the kids on 1st floor. Location was very...
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    About this property
    ***7071 Bond Street*** Tastefully decorated townhouse with many new appliances, screen porch and convenient in town location. Offers Wi-Fi. 2 bedrooms and 1 bath downstairs/1 bedroom and 1 bath upstairs.*** Bed Sizes: 1 King, 1 Double, 2 Twin, 1 Queen Sleep Sofa*** Prime Season Rates: $650...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Water's Edge1 / 34
    (4)Very good
    1.1 kilometres from Wine Cheese & More
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • DVD Player
    • Washer
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 May 2017
    Water's Edge is in a great location - right on the water and close enough to walk into town. The house was clean and equipped with anything you might need. As mentioned in...
    Reviewed 17 October 2016
    This recently renovated home features an open floor plan with wrap around windows facing out to the water. The small watch tower at the top of the house has stunning views and...
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    About this property
    Water's Edge is an adorable Bay Front cottage in walking distance to Chincoteague's Historic Downtown. You'll be impressed by the charm of this home from the time you pull in the driveway. On the first floor you'll find a full bathroom with an open great room with expansive bay views. There is a...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    Mystical Sand1 / 10
    (3)Excellent
    0.7 kilometres from Wine Cheese & More
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 January 2018
    We love staying at this lovely little home Very clean! the painting really made you feel like you where at the beach at all times. and close to a couple of the stores so easy...
    Reviewed 10 July 2017
    We (my wife, son, mother-in-law, wife's aunt, and myself) stayed here last summer. My son was only a year old so it was really only 4 full grown people. We loved the location...
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    About this property
    ***6096 Taylor Street*** Perfect retreat for the traveler on a budget! Tastefully decorated cottage with 36 inch television and within walking distance of shops and restaurants. All bedrooms on same level.*** Bed Sizes: 1 Queen, 2 Twin, 1 Queen Futon*** Prime Season Rates: $650 weekly/$130 per...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Bay Daze1 / 17
    (2)Very good
    0.2 kilometres from Wine Cheese & More
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 July 2018
    We stayed at Bay Daze last July and just loved it so we booked again for the same week this summer. Here are the positives:-The view of the bay is stunning and I spent every...
    Reviewed 30 August 2017
    A beautiful condo with nautical decor, comfortable beds, well-stocked kitchen, large refrigerator and 2.5 baths. Two balconies provide gorgeous views of the waterway, marsh and...
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    About this property
    Escape from the hustle and bustle of everyday life at this little slice of paradise nestled on the edge of the Chincoteague Bay! Bay Daze is a clean, comfortable and modern townhome (end unit) offering all the amenities you'll need for a perfect vacation! On the main level you'll find an open...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Shear Water1 / 12
    (1)Excellent
    0.4 kilometres from Wine Cheese & More
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***6347 Jester Street*** Unique Pet Friendly Chincoteague home located in town within walking distance to shops and restaurants. Has large fenced in back yard and a private outside rinse area.*** ***New HVAC-Central heating and Air for 2018*** Bed Sizes: 1 King, 2 Twins, 1 Daybed with Trundle***...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.2 kilometres from Wine Cheese & More
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Do you need a vacation rental where you can park your boat and bring your pet? You've found it! Sea Tag #23 is a great two bedroom unit (upper level) that overlooks beautiful Assateague Island. Enjoy relaxing on the covered porch after a day of fishing. The views of Assateague are fantastic and...
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    Location Information
    Chincoteague Island, Virginia
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    0.4 kilometres from Wine Cheese & More
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A stunning condo that offers you all of the comforts of the Sunset Bay Villa community. Enjoy the community pool and fitness center! This is one of the pet friendly units at Sunset Bay. Note: This villa does not have a boat slip. Additional amenities include: 2 pets max. max. pets allowed, 2...
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    Location Information
    Chincoteague Island, Virginia
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1.3 kilometres from Wine Cheese & More
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***7141 Wayne Road*** Welcome to Blue Pearl Cottage, a lovely, sunny beach house, just minutes from fabulous beaches, wildlife and the quaint downtown of Chincoteague. This airy cottage nestled beside pine woods has a large wrap-around deck, a screened porch and offers privacy and quiet, with all...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.1 kilometres from Wine Cheese & More
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Terrace
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***6242 Church Street*** Proud 3 story Traditional home located at the edge of town is rich in detail and history of the island. Beautiful renovations make this home just right for the whole gang. Just a few steps and walk to shopping and waterfront downtown plaza. Spacious rooms and large...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Sunset Bay Villa 2091 / 28
    (1)Very good
    0.4 kilometres from Wine Cheese & More
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 September 2015
    This unit is easily accessible, and nicely decorated. It truly felt like home for a week. Its a short walk to restaurants, shops, and groceries in downtown. Sit on the deck...
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    About this property
    A sense of the tropics! This British Colonial style villa is one of our most popular villas. You can enjoy romantic sunsets on the waterside balcony at the end of the day, or enjoy a soothing soak in a luxury jetted tub located in the master bath. Sunset Bay amenities (outdoor pool, fitness room...
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    Location Information
    Chincoteague Island, Virginia
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Serendipity1 / 20
    (2)Very good
    0.7 kilometres from Wine Cheese & More
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come stay in this classic Eastern Shore Style home. Located just a few blocks from our famous downtown Main Street area, you are within walking distance to most of our shops and restaurants. Serendipity has a very nice screened porch for those memorable Chincoteague Summer evenings. This home also...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Canalside Chincoteague Island Home w/ Pier!1 / 26
    (2)Very good
    1.4 kilometres from Wine Cheese & More
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Patio
    • Balcony
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Terrace
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 November 2017
    What a wonderful house to spend the week. A great place to relax after watching rockets, exploring light houses, and combing the beach. Lots of crabs to come home to. Superb.
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    About this property
    Leave all of your worries behind when you stay at this marvelous 3-bedroom, 2-bathroom Chincoteague Island vacation rental house! Boasting space to sleep 8 guests, water views and a secluded canalside location with private pier, this quaint trailer-style property will allow you to leave all your...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    0.5 kilometres from Wine Cheese & More
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • Terrace
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***4312 Main Street*** Enjoy the water view from this immaculate home offering spacious rooms and a quiet location off Main Street. All bedroom on the same level.*** Bed Sizes: 3 Queen, 1 Double Futon*** Prime Season Rates: $775 weekly/$155 per night. Off Season Rates: $600 weekly/$120 per...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    Sundance1 / 20
    (3)Excellent
    1.2 kilometres from Wine Cheese & More
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • DVD Player
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 September 2017
    Our stay was AMAZING!! Our family of 7 loved everything about this rental! Clean house, more than enough room for all of us, 3 full bathrooms! Quiet, welcoming home! We...
    Reviewed 1 August 2017
    This house is spacious, comfortable, well decorated, and labeled. Yes, labeled! The owner has every switch, cupboard, drawer, and remote labeled, which we really appreciated, as...
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    About this property
    Light, bright and airy - this beautiful home is very well maintained, tastefully furnished and boasts all amenities including screened porch, outside shower, all appliances including washer/dryer, tvs in every bedroom and more. The home is located just outside of town and offers a very quiet...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    Sunset Bay Villa 1111 / 18
    (2)Excellent
    0.5 kilometres from Wine Cheese & More
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 September 2016
    This place is really niiice!! Very spacious, modern kitchen.nice size bedrooms. Night time view off the living room/bedroom deck beautiful! It's very peaceful. I enjoyed...
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    About this property
    This 3 bedroom 2 bathroom luxury villa features a first floor, open floor plan villa for easy access, and it is dog friendly! The first bedroom offers a twin trundle bed, the second bedroom has a queen bed, and master suite has a queen bed with a private bathroom and access to the waterfront deck....
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    Location Information
    Chincoteague Island, Virginia
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Horseshoe Haven1 / 14
    (1)Very good
    1.1 kilometres from Wine Cheese & More
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 August 2018
    Cannot say enough about this wonderful rental & Harbour Realty. House was very clean & well stocked. A great family rental and a plus was being able to bring out pup...
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    ***7111 Horseshoe Lane*** Lovely home centrally located on a quiet residential street. Watch the Saltwater Cowboy's saddle up for the pony round ups right from the comfort of the airy screened porch. Too hot at the beach, no problem than enjoy the pool. This home has all the amenities for beach...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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    Great White1 / 23
    (5)Very good
    0.4 kilometres from Wine Cheese & More
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 March 2015
    We loved this rental property. Lots of room and places to hang out with friends and family. The deck was great in the evenings for a glass of wine :)Our kids really enjoyed...
    Reviewed 12 March 2015
    I have stayed in this house may times with my family and have had a wonderful time. Is spacious and have all the commodities needed for our group (we were nine). Very quiet and...
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    About this property
    Huge 5 bedroom, 2.5 bath Victorian home right on Main Street - close to downtown. Great White is pet friendly & big enough to accomodate 12! Fantastic wrap-around screened porch out front! This home includes access to a swimming pool and fitness center at Sunset Bay Villas. Amenities include a...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 12
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    0.2 kilometres from Wine Cheese & More
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ****6300 Church Street **** Affordable vacation rental in historic downtown Chincoteague. Walk to shops, restaurants, fishing pier, waterfront park and farmers market. First floor bedroom, both bathrooms downstairs. Enjoy the back screened porch after the beach or relax in the front porch swing....
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Misty Sails1 / 13
    (1)Very good
    1.3 kilometres from Wine Cheese & More
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Balcony
    • Private Outdoor Pool (Unheated)
    • Terrace
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    We enjoyed our stay at this house. The only reason I did not give a 5 star review was that we use the broiler a lot on vacation and the broiler was not working at the time of...
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    About this property
    ***7136 Silver Sails Landing*** Spacious duplex overlooking the wetlands. With screen porch, deck, first floor master suite, enjoy the community pool after a long day at the beach! Next door to Bay Pony.*** Bed Sizes: 2 King, 2 Twin*** Prime Season Rates: $1350 weekly/$270 per night. Off Season...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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