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Holiday Homes in Wingdale

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    Don't let other travellers get your favourite Wingdale area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 18 Rentals in Wingdale
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    Wingdale
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    The following rentals are within 25 kilometres of Wingdale.
    Verbank
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Roxbury, CT
    4 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    Washington, CT
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Parking
    • Private Garden
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    South Street is a mint condition 4 bedroom home with a heated pool, wonderful flat private quiet yard with a swing set far back from the street. The home is in Washington, the most desirable historic rural town in Litchfield County with wonderful restaurants, land preserves, private schools,...
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    06793, Washington, Connecticut
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    20'x40' inground private pool just for you&house with 4bedrooms1 / 36
    (4)Excellent
    New Milford, CT
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Washer
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 August 2014
    This is a spacious 4 bedroom property. it is high above the local road and is surrounded by trees. Neighbours are a good distance away, so the loudest sounds are from the local...
    Reviewed 21 July 2014
    A spectacular week in a secluded spot and yet minutes from quaint New Milford Village. Pool is GREAT
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    About this property
    LITCHFIELD COUNTY, New Milford, CONNECTICUT Beautiful!! very private country setting; four bedrooms, large family room with cathedral ceilings and grand piano. All amenities: cable TV, CD, DVD,VCR, internet and air conditioning. Deck--including a screen house; gas grill. 20x40 inground pool with...
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    06776, New Milford, Connecticut
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Rhubarb Hill, a Charming 1850's Farmhouse1 / 21
    (1)Excellent
    New Preston, CT
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Central Heating
    • Wi-Fi
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 July 2014
    We arrived all type A with many plans to hike and swim, ended up enjoying the comfort of the house, cooking, hanging out together. Switching from indoor seating for outdoor...
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    About this property
    Near Lake Waramaug $300 per night with a 3-night minimum $1800 per week. June $6,000 per month July $6,000 per month Aug $6,000 per month Memorial Day to Labor Day $14,000. During the winter months-mid-October-mid-March, I seek long term rentals. I only rent by the month during this...
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    06777, New Preston, Connecticut
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    New Milford, CT
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    1840 completely renovated country house with lots of room, convenience and quietness. 4,000 sq. ft. furnished with many antiques. A most unique country kitchen, formal dining room, eat-in kitchen, library, living room, den, five bedrooms (some have 'Sleep Number' mattresses), and 5 and a half...
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    06776, New Milford, Connecticut
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Sherman, CT
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Washer
    • Mountain Views
    • Grill
    • Housekeeping Included
    • Waterfront
    • Central Heating
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private secure community with million dollar homes. Perfect weekend retreat. 90 minutes from NYC. This two bedroom cottage has all the necessary amenities. Includes access to two private beaches on Candlewood Lake and Green Pond. Just renovated with new wood floors, new appliances, new...
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    06784, Sherman, Connecticut
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Private Lakefront & Pool DeeLuxGlamping. NYC Getaway1 / 31
    (1)Excellent
    Pawling
    2 Bedrooms, 1 Bathroom, Sleeps 12 Quick View
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    Amenities & Details
    • Parking
    • Private Outdoor Pool (Heated)
    • Mountain Views
    • Waterfront
    • Air Conditioning
    • Private Garden
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 September 2017
    Love the place. It was great for our family. Very spacious and clean. The place is also located in a great area so it was perfect. We will rent it again next year for our...
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    About this property
    You will have full access to this 2 bedroom camper that sleeps 12. We are located on a private/quiet road. This is not a camp ground. You will be the only family staying with us. We have a huge in ground salt water system pool that you will have full access to. We live here on the grounds, so the...
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    12564, Pawling, New York
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 12
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    Lake Bliss the Perfect Getaway1 / 20
    (9)Very good
    Holmes
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Washer
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 September 2016
    Review received! Just one more thing to do…We have received your review for Property #141424 Once you confirm it, we can work on getting it live! Read the review below; if...
    Reviewed 6 July 2016
    Great little getaway for the weekend. Really enjoyed the lake, the barbecue, and the canoes. There isn't much else to do, so a long vacation may not be the best idea. I think an...
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    About this property
    Fully furnished gorgeous home directly on beautiful Whaley Lake only 1-1½ hours from New York City. Two levels each with full kitchen and bath. Washer & dryer, wireless internet, plenty of parking. The units can be rented separately or together. Lower level with huge panoramic windows overlooking...
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    12531, Holmes, New York
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    LaGrangeville
    2 Bedrooms, 2 Bathrooms, Sleeps 3 Quick View
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    Amenities & Details
    • Washer
    • Mountain Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Secluded on a knoll of Norway Spruce, atop eight acres, Frank Lloyd Wright associate Aaron Resnick's Mid-Century Modern (MCM) design is a classic example of organic Usonian architecture. This Usonian home features a completely private setting with a pool. The home is located in the heart of the...
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    12540, LaGrangeville, New York
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 3
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    New Preston, CT
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Waterfront
    • Internet Access
    • Washer
    • Cable/satellite TV
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Visit the beautiful shores of Lake Waramaug in this charming 3-bedroom, 2-bathroom New Preston vacation rental cottage that comfortably sleeps 6. Relax and recharge on the brand new stone patio and spend your days by the water on the private lakefront area and 22 foot dock. With 1,300 square feet...
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    Location Information
    06777, New Preston, Connecticut
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Roxbury, CT
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Private Garden
    • Mountain Views
    • Air Conditioning
    • Grill
    • Secure Parking
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The best way to experience Roxbury Connecticut... A completely Private Apartment in Modern contemporary home located on Route 67 in Roxbury Connecticut. 2 Bedrooms, Full Kitchen, Full Bathroom, Living Room, Oversized Deck, Outdoor Grill, and 3+ Acres of Land with Outdoor Seating. Close to...
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    06783, Roxbury, Connecticut
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    New Fairfield, CT
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Patio
    • Internet Access
    • Parking
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Savor a piece of Connecticut paradise at this 3-bedroom, 2-bathroom New Fairfield vacation rental house! Suitable for up to 10 guests, this Hampton-style home featuring an outdoor kitchen and 4 levels of outdoor space provides travelers with an ideal location on Candlewood Isle, where you can enjoy...
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    Location Information
    06812, New Fairfield, Connecticut
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    LaGrangeville
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cozy, quiet & quaint space overlooking tranquil pond surrounded by trees and nature, and within a mile of essentials. Catch your breath & hear yourself think. Serene setting to get away from the day-to-day and unwind. Great secluded spot to read, write, work or just rest. The surroundings light up...
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    12540, LaGrangeville, New York
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Amenia
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Private Garden
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Magnolia Cottage!! 44,000 Gallon in-ground saltwater pool. Covered Front Porch with wicker chairs. Gardens, Greenhouse, & Walking Trails. Side Patio with BBQ and Gas Fire Pit. Basic Stocked Fridge (milk, eggs, butter, jams, etc.). High thread-count cotton linens and towels. Two...
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    12501, Amenia, New York
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Warren, CT
    7 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Washer
    • Hot Tub
    • Air Conditioning
    • Waterfront
    • Patio
    • DVD Player
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    **Please note that this property can be rented alongside with VRBO listing 3921932ha (Evolve #256841) for discounted rates. Please inquire for additional information** When searching for the perfect place to stay for your next peaceful family gathering, 'Carriage House' is just the spot for you....
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    06777, Warren, Connecticut
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 16
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    Kent, CT
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This classic 19th century victorian home is located in the heart of downtown Kent, CT. The Kent Victorian is across the street from So Delicious Homemade Bakery, restaurants, The IGA Super Market, Ace Hardware Store, dry cleaner, Webster Bank and other stores. The Kent Victorian Vacation Rental is...
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    Location Information
    06757, Kent, Connecticut
    Private Room - 2 Bedrooms, 1 Bathroom, Sleeps 3
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