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Holiday Rentals in Chesapeake

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    €143 Average
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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 15 Rentals in Chesapeake
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    Chesapeake Bay "BigBay" Beach House1 / 19
    (20)Excellent
    Chesapeake
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    The following rentals are within 15 kilometers of Chesapeake.
    Caicos Cottage (A Beach Lover's Dream)1 / 30
    (2)Very good
    Norfolk
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Norfolk
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Norfolk
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Air Conditioning
    • Waterfront
    • Grill
    • DVD Player
    • Satellite TV
    • Wi-Fi
    • Ocean Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy our beautiful five bedroom home within steps to the Chesapeake Bay. Huge master bedroom and expansive views of the bay. Opening living space, with three large out door decks. Please visit Vacation Rental By Owner to book. Property number 717981. Fish, Hunt for Shells, or just walk...
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    Norfolk, Virginia 23518
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    Mid-Century Modern Lakefront Estate: Bay & Beach1 / 38
    (8)Excellent
    Norfolk
    2 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Satellite TV
    • Washer
    • Housekeeping Included
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 May 2017
    The location was great loved every minute of itthe house is so beautiful and comfortable and oh the owner Chuck was so nice to was he went above and beyond for instance I went...
    Reviewed 9 November 2016
    It was a little weird to have the homeowner in the house with us, but he was helpful and gave good suggestions for things to do.
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    About this property
    Welcome to Wiseacre, an expansive, private estate reminiscent of Frank Sinatra, Dean Martin & Sammy Davis Jr.—with a dash of “Mad Men." This award-winning whimsical 4000sf Frank Lloyd Wright-inspired Mid-Century Modern home offers a relaxing retreat from the rat race (if not the rat pack)....
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    Norfolk, Virginia 23518
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 12
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    Norfolk
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Balcony
    • Internet Access
    • Washer
    • Air Conditioning
    • 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 close walking distance of the Chesapeake Bay. With 3 bedrooms, 3.5 baths, and a prime location near ample major Virginia attractions, including Ocean View Pier, Ocean View Golf Course, Norfolk's downtown and...
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    Norfolk, Virginia 23503
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    *New Listing for 20171 / 20
    (1)Excellent
    Norfolk
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Terrace
    • Balcony
    • Parking
    • 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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    Location Information
    Norfolk, Virginia 23518
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    2 Bedroom |Family-Friendly Vacation Rental - Walk To Beach1 / 12
    (19)Very good
    Norfolk
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Satellite TV
    • Secure Parking
    • Air Conditioning
    • Patio
    • Washer
    • Private Garden
    • Wi-Fi
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    We went to Virginia to see the beach & watch our daughters play volleyball at Va Wesleyan. We don't like the run-of-the-mill hotels or condo-style VRBO's. So this quaint 2 BR...
    Reviewed 4 weeks ago
    The previous reviews way overstate these accommodations.The good:*Justiana checked on us twice. Great service!*The short walk to the beach was nice and the beach was...
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    About this property
    This ground floor, two bedroom, fully furnished summer rental is your home away from home in a nice relaxed area; you will find peace tranquility and beauty off this ocean view. With only a 3 minute walk to the beach, you will find lots to do plus enjoy free live music on the weekends. Your stay...
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    Norfolk, Virginia 23503
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Norfolk
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Private Garden
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious cottage on 0.6 acres has a wonderful view of the Elizabeth River. The interior was recently renovated with a new kitchen and floors, a washer and dryer. The kitchen is fully equipped including a Keurig coffee machine. Breakfast is provided, and the sunrise over the water is...
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    Norfolk, Virginia 23502
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Parking
    • 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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    Location Information
    Norfolk, Virginia 23503
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Norfolk
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Internet Access
    • Grill
    • Air Conditioning
    • Parking
    • DVD Player
    • Satellite TV
    • Patio
    Suitability
    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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    Location Information
    Norfolk, Virginia 23503
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Norfolk
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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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    Location Information
    Norfolk, Virginia 23503
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    Amenities & Details
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 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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    Location Information
    Norfolk, Virginia 23518
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Norfolk
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Internet Access
    • Balcony
    • DVD Player
    • Terrace
    • 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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    Location Information
    Norfolk, Virginia 23510
    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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    Amenities & Details
    • 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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    Location Information
    Norfolk, Virginia 23518
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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