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Holiday Homes in Chesapeake

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    Don't let other travellers get your favourite Chesapeake area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 25 Rentals in Chesapeake
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    Stay at the Quay!1 / 30
    (2)Excellent
    Chesapeake
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Big Bay- A Private Beach front Home on the Chesapeake Bay1 / 57
    (23)Excellent
    Chesapeake
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    The following rentals are within 15 kilometres of Chesapeake.
    Beautiful Waterfront Cottage Near Downtown Norfolk with Private Dock and Sunroom1 / 51
    (3)Excellent
    Norfolk
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Norfolk
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Secure Parking
    • Private Garden
    • Air Conditioning
    • Wi-Fi
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This comfortable three bedroom house is located in a quiet neighborhood. The house has a real homely feel to it. Newly renovated to put you in a mellow mood while relaxing in a fresh new look. All in all a great living area, with a fully equipped kitchen, two Queen sized beds, two singles (+one...
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    23503, Norfolk, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Community
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Private Garden
    • Wi-Fi
    • Secure Parking
    • Air Conditioning
    • Grill
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Soft water system throughout the house and reverse osmosis water filtration for drinking and cooking. Guests have access to Hulu and Netflix in 2 of the bedrooms and the living area, basic cable only in the living room. Board games are available (Apples to Apples, Headbandz, Taboo), dining room...
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    23452, Community, Virginia
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Grill
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Charming 3 bedroom 2 and 1/2 bathroom 1,672 sq. ft townhouse is equipped with everything you need to feel completely furnished with your comfort in mind. So if you decide to relax inside and enjoying a home cooked meal away from home. Guess what! We've got the bases covered. We provide a fully...
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    23453, Community, Virginia
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    Norfolk
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Internet Access
    • Balcony
    • DVD Player
    • Terrace
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Exquisitely furnished 1bdrm New York loft style luxury condo with interior brick, and Brazilian hardwood floors throughout. Stainless steel island with industrial grade updraft and ventilation system. Granite counters throughout kitchen and master bath. Flat screen 3-D television with your favorite...
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    23510, Norfolk, Virginia
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Norfolk
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Apartment is 2 blocks from the beach. You’ll love it because of the new pillow-top comfy bed, the kitchen, and the condo is modern and cozy. It's a comfortable one bedroom end unit and the master sleeps two, but the futon pulls out to sleep another two. It's good for couples, solo adventurers,...
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    23518, Norfolk, Virginia
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    *New Listing for 20171 / 20
    (1)Excellent
    Norfolk
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Terrace
    • Balcony
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    • Washer
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note that the pictures show the house unfurnished. However updated pictures will be uploaded as soon as possible. Great home for the summer season. This home is fully furnished ready to receive you and your family! Great open floor plan for entertaining along with enough room for...
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    23518, Norfolk, Virginia
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Norfolk
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sandswept Carriage House - Luxurious and Spacious Cathedral Ceiling Open Floor Plan Fully Furnished Executive Jumbo 1BR 1.5BTH at the beach includes EVERYTHING! Everything means furniture, pots, pans, dishes, linens, electricity, cable, wifi, water, trash, washer/dryer. Apartment is above a...
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    23503, Norfolk, Virginia
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Norfolk
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
    • Waterfront
    • Hot Tub
    • Ocean Views
    • Balcony
    • Patio
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A picture is worth a thousand words so just look at the views of the sunrise from your master suite. Then crawl into your indoor hot tub and watch the dolphins jumping each morning and night. When the urge strikes you walk down to the beach and just take a deep breathe. If you are up for some...
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    23503, Norfolk, Virginia
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Norfolk Apartment - Walk to Beach & Chesapeake Bay1 / 24
    (1)Very good
    Norfolk
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
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    • DVD Player
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pack your swimsuits and head off to the Chesapeake Bay by booking this 2-bedroom, 2-bathroom vacation rental apartment in Norfolk. Complete with all the comforts of home, this classic home offers 2 stories, 1,200 square feet of living space, and accommodations for up to 5 guests! With the beach...
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    23503, Norfolk, Virginia
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    *Waterfront**10 Mile View**Hot Tub**Pet Friendly**1 / 31
    (1)Excellent
    Norfolk
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
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    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 August 2016
    Very nice house. On the water looking at a marina & across the river is a Naval yard with aircraft carriers, destroyers, and daily helicopters practicing. Even a seal...
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    About this property
    This house has waterfront views from every Room! Crabbing/fishing off large deck, (1 of 4 decks) Owned/managed by military veteran, (thanks for your support)! **Sail boat races on Thursday can be seen from the decks & giant ships! **BEACHES ** 50 steps behind home is a small community beach, 3...
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    23503, Norfolk, Virginia
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Cozy Mother-in-Law Suite1 / 7
    (1)Excellent
    Norfolk
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 November 2016
    After my trip from Dallas it was nice to walk in to a place that felt just like home even for such a short stay. Very well kept, clean and fresh. I would definitely recommend...
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    About this property
    This carefree suite is fully furnished for a comfortable experience. We provide all bed and bath linens for your convenience. just bring your bags and the rest is waiting for you. Our suite offers a quiet beach environment... but for those wanting a night on the town....the Virgina Beach Boardwalk...
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    23518, Norfolk, Virginia
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Engleside
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
    • Washer
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A coastal Virginia getaway awaits up to 6 guests at this 2-bedroom, 1-bath vacation rental near Wayne Creek in Norfolk. Well-maintained, beautifully decorated and ready to provide you with a comfortable retreat, this home offers easy access to the city's best attractions - just 10 minutes from...
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    23509, Engleside, Virginia
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Norfolk
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sail away in your dreams on this adorable Vintage sailboat! A truly unique experience, walking distance to the beach through the pristine East Beach neighborhood. Basic creature comforts in a gorgeous spot! Hang out with the local 'pirates' at the Lagoon and swap stories of adventures on the high...
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    23518, Norfolk, Virginia
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Community
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Air Conditioning
    • Cable/satellite TV
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Virginia Beach Vacation Paradise. 3 bedroom, 2 bath home centrally located for access to town center, the beach, and local attractions. More information The space- Our home is warm and welcoming so make yourself at home and enjoy your stay. It's all yours! You'll only need to share the space with...
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    23453, Community, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Norfolk
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for an affordable location 50 steps from the beach? This 2 bedroom, 1 bath apartment leads to a walkway with stairs to a white sandy beach on the Chesapeake Bay. The very affordable rental rate offsets not being able to see the beach from the apartment, but 50 steps cannot be beat for the...
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    23503, Norfolk, Virginia
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Engleside
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    • Air Conditioning
    • Terrace
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled in Ocean View, 'Shiloh Bay Beach House' is ready to host your next east coast getaway! This 2,200-square-foot townhome easily accommodates 12 guests with 4 bedrooms and 3.5 bathrooms, plus all of the comforts of home. There's even a private balcony and gas grill. But the vacation rental's...
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    23518, Engleside, Virginia
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Norfolk
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Terrace
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come visit this lovely bayside Norfolk vacation rental townhome, ideally settled within walking distance of the Chesapeake Bay. With 3 bedrooms, 3.5 bathrooms, 2,437 square feet, and accommodations for up to 8 guests, this is the perfect home for families of all sizes! You'll love the prime...
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    23503, Norfolk, Virginia
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Engleside
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    • Washer
    • Ocean Views
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The perfect stay for friends and family seeking an east coast getaway, this home features 3 bedrooms, 2.5 bathrooms, and room for 6 guests! All of the comforts of home and modern amenities, like a fully equipped gourmet kitchen, wireless internet connection and a gas grill, come together to create...
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    23518, Engleside, Virginia
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Engleside
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • Washer
    • Patio
    • DVD Player
    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled in Ocean View, 'Sealah Sanctuary Beach House' is ready to host your next East Coast getaway! This 3,000-square-foot vacation rental townhome easily sleeps 12 guests with 4 bedrooms and 3.5 bathrooms, plus all of the comforts of home. There are outdoor decks and balconies on every level...
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    23518, Engleside, Virginia
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Norfolk
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come soak up the sun at this 2-bedroom, 1-bathroom Norfolk vacation rental apartment, ideally situated within close walking distance of Chesapeake Bay. With accommodations for 5 people, this beach getaway property boasts tasteful nautical decor, a view of the bay, and tons of nearby beachside...
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    23503, Norfolk, Virginia
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Engleside
    4 Bedrooms, 2 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Book an unforgettable beach vacation to this homey 4-bedroom, 2-bathroom vacation rental home in Virginia Beach. Located within 20 minutes of the beach and boardwalk, this 1,764-square-foot home for 14 is perfect for those looking to soak up the sun. When you aren't swimming at Little Creek Beach...
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    23464, Engleside, Virginia
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 14
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    Engleside
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Patio
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    • Grill
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape your busy schedule for an east coast retreat at this vacation rental townhouse in Virginia Beach! This 2-bedroom, 2-bathroom, duplex-style property is best suited for 4 guests, with a comfortable interior, old-world architecture, and plenty of backyard space located right on the lake. Not to...
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    23455, Engleside, Virginia
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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