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Chincoteague Island Vacation Rentals

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    Travelers to Chincoteague Island are booking July dates now. Secure your vacation rental today, and have the perfect trip.
    All 343 Rentals in Chincoteague Island
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    ***6559 Church Street***Island home with large back yard and deck and Internet. Pet Friendly! Nearby is Chincoteague Crossing. 2 bedrooms and 2 baths downstairs/2 bedrooms upstairs.***Bed Sizes: 1 Queen, 1 Double, 4 Twin***Prime Season Rates: $795 weekly/$159 per night.Off Season Rates: $550...
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    Chincoteague Island, Virginia 23336
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Studio, 2 Bathrooms, Sleeps 8 Quick View
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    Coastal Breeze is a modern 3 bedroom, 2 bathroom home located on Bay Colony Drive off of North Main Street. You know as soon as you walk into this house that you are at the beach. There are tiled floors throughout the entire house with the exception of carpet in the bedrooms. The first floor offers...
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    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    ***5175 Coley's Lane***Totally remodeled traditional island home. Perfect for your vacation getaway! Located on private lane with large back yard. Master suite with sitting area. Two additional bedrooms and loft. Short distance to seafood market and boat launch.Bed Sizes:1 King, 1 Double, 3...
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Conch Shell1 / 14
    (2)Very good
    Studio, 1 Bathroom, Sleeps 7 Quick View
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    The house is located on Pine Drive on Piney Island, closest neighborhood to the beach and convenient for shopping and dinning on Maddox Blvd. This wonderful waterfront beach bungalow features a wrap around deck with views of Assateague and the light house. You can bring your boat, jet skies or...
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    Chincoteague Island, Virginia 23336
    Rental Home - 1 Bathroom, Sleeps 7
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    Studio, 3 Bathrooms, Sleeps 8 Quick View
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    Bay Dreamer is a spacious 3 bedroom duplex home with multiple porches and decks and spectacular sunset views, just minutes from downtown. When you enter the home you'll find a furnished rec room. The second floor is an open living room (queen sleeper sofa), dining area and kitchen that have all...
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bathrooms, Sleeps 8
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    SNUG HARBOR WATERFRONT COTTAGE with a stunning lighthouse view!1 / 49
    (35)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
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    It's a celebration of nature in its most magnificent form, as the wild Chincoteague ponies run up and down the marshland, the local birds will sing you a song. As this perfect day comes to an end, the laid back reggae tunes will set the mood for the miraculous montage of Caribbean colors that make...
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    Chincoteague Island, Virginia 23336
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    ****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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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    ***3241 Mulberry Lane***Immaculate waterview home with super large screen porch. It has a great kitchen for cooking large meals. This home is in a nice, quiet location that sits at the end of a cul-de-sac and is in walking distance to carnival grounds. All bedrooms on the same floor.***Wi-Fi for...
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Studio, 3 Bathrooms, Sleeps 10 Quick View
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    Luxury waterfront home in Salt Marsh Landing. Spectacular sunsets. A long, private pier over the salt marsh leads you to a bay front dock area with shade. It's perfect for crabbing, fishing or canoe and kayak launching. Well appointed and architecturally pleasing, Castlebar features a main level...
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    ***6301 Circle Drive***Charming pet friendly cottage in serene island setting with easy access to the Beach and to the Old Town. Spacious yard and screened porch. 2 full bathrooms. Bedrooms include 1 large master BR with king-size; plus 1 BR with 2 twins; and a cozy den with sofa/sleeper. Pet...
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Bayside1 / 14
    (3)Very good
    Studio, 3 Bathrooms, Sleeps 10 Quick View
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    Luxury waterfront townhome overlooking Chincoteague Bay. Beautiful sunsets. Long pier (shared) for fishing & crabbing. All amenities including all appliances, central air and enclosed porch (with a/c). Need more room? Bayside already booked? Try our sister homes right next door, Sunset Dreams or...
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bathrooms, Sleeps 10
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    A Shore Thing1 / 16
    (3)Very good
    Studio, 3 Bathrooms, Sleeps 8 Quick View
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    A very nice waterview duplex overlooking Assateague Island and the lighthouse. Located across the street from "Mr. Baldy's Restaurant" and within walking distance to Memorial Park park (where there is a boat ramp, a fishing pier, and play area for the kids). Enjoy the waterside screened porch....
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bathrooms, Sleeps 8
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    Studio, 4 Bathrooms, Sleeps 8 Quick View
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    Enjoy some of the island's best water views overlooking Oyster Bay from nearly every room of this custom beach home! Located on a bulk-headed waterfront lot in Richardson's Landing, you can fish and crab from the backyard! A wonderful feature of this spacious home is that you'll find your bedrooms...
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    Chincoteague Island, Virginia 23336
    Rental Home - 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    ***6317 Teal Lane***Affordable Getaway. Great Location, walk to restaurants, ice cream parlors and amusements. WiFi Available.*** This Property accepts Dogs 50lbs and Under Only. No Cats. ***Bed Sizes: 1 Queen, 1 Twin, 1 Bunk (2 Twins), 1 Double Sleep Sofa***Prime Season Rates: $750 weekly/$150...
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    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 7
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    Sunset Bay Villa 2031 / 15
    (1)Average
    Studio, 2 Bathrooms, Sleeps 8 Quick View
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    Villa 203 is a new unit that has been professionally decorated and offers five-star luxury. Spacious and accommodating, the gourmet kitchen is perfect for cooking your favorite meals. It's well stocked and ready for your handiwork. There are three bedrooms, including a master bedroom suite with...
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    Chincoteague Island, Virginia 23336
    Condo/Apartment - 2 Bathrooms, Sleeps 8
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    Studio, 3 Bathrooms, Sleeps 6 Quick View
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    A light, bright and airy beach rental with community pool and water access with shared dock. The spacious 2 bedroom, 2.5 bathroom home is tastefully furnished and features all appliances including washer/dryer and dishwasher. Wireless internet is included. Come and enjoy a great stay! Additional...
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    ***6265 Hancock Lane***This historic island home is immaculate and totally renovated for 2015! Tucked away on a private lane with a large screened porch overlooking a lovely yard. A perfect spot to unwind and enjoy your beach vacation! Remodeled kitchen and bath, new laundry room, spacious...
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    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Great White1 / 23
    (5)Very good
    Studio, 3 Bathrooms, Sleeps 12 Quick View
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    • Shared Outdoor Pool (Unheated)
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    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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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bathrooms, Sleeps 12
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    Studio, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
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    This property has a location that is rich with amenities. Situated right next to Memorial Park, you can sit on the deck and enjoy the water views as the kids run, play, skateboard, fish and crab. The first floor is an open room consisting of the kitchen, dining area and living room (with queen...
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    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bathrooms, Sleeps 6
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    Green Heron1 / 10
    (1)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    ***4560 Shelley Cove Lane - Smugglers Cove***Private, secluded neighborhood. Very natural wooded setting with water access available. Next door to Pine Cove Place and Serenity Now. Water access is for kayaks and canoes. 2 bedrooms and 1 bath downstairs/2 bedrooms and 1 bath upstairs.***This...
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    Chincoteague Island, Virginia 23336
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Admiral Benbow1 / 10
    (1)Excellent
    Studio, 3 Bathrooms, Sleeps 8 Quick View
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    A very nice contemporary home located in Oyster Bay I. Located next to the community boat ramp - you have access to the water and the kids can fish and crab from the dock areas. This house has an outdoor ramp to the ground level. Don't miss out on the great screened porch for a family dinner. Bed...
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bathrooms, Sleeps 8
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    Cool Shack1 / 8
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    ****6382 Church Street****Pet Friendly. This vintage inspired cottage is perfect for a couple or small family and your four legged friend! Centrally located only two blocks from historic downtown’s shops, restaurants and farmer’s market. Lovely cared for home with ceiling fans in every room,...
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    Chincoteague Island, Virginia 23336
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Eagle's View1 / 38
    (5)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    Eagle's View is a luxury vacation rental overlooking the Assateague Island Channel and lighthouse. Fully equipped for comfort and convenience, this house is your home base for quick access to beaches, Eastern Shore attractions, and natural beauty. In addition to basking on the unspoiled beaches,...
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    Chincoteague Island, Virginia 23336
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    ***7518 Doe Bay Lane***Beautiful waterview 3 bedroom, 2.5 Bath Duplex with waterside balcony, fully equipped kitchen, comfortably furnished.***Bed Sizes: 2 Queen, 2 Twin, 1 Queen Sleep Sofa ***Prime Season Rates: $1195 weekly/$239 per night.Off Season Rates: $775 weekly/$155 per night.Pony Penning...
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Studio, 3 Bathrooms, Sleeps 8 Quick View
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    Wow, what a deal! This magnificent 5 bedroom, 3 bathroom waterfront home is perfect for your family vacation. Offering two first floor bedrooms one with a twin trundle bed and en suite bath, the second bedroom has a double bed. The large open rooms that sprawl the first floor include two spacious...
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bathrooms, Sleeps 8
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    Big Pines1 / 9
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    ***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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    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Studio, 1 Bathroom, Sleeps 6 Quick View
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    Take a step back in time at this lovely little cottage. What you won't find are the modern-day "connectivity" features - there is no cable TV or internet. This is the perfect spot to disconnect and just enjoy your time at the beach! Prime Time is located in Piney Island;just a short distance from...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 1 Bathroom, Sleeps 6
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    Heron's Cove On Salt Meadow1 / 16
    (1)Excellent
    Studio, 5 Bathrooms, Sleeps 10 Quick View
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    Peaceful and stunning waterfront home! Located on a quiet side-street, Heron's Cove features a reverse floor plan with all bedrooms on the first floor, and the main living-level on the second floor. This allows you to capture and maximize the fabulous bay views! The second floor also features a...
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    Chincoteague Island, Virginia 23336
    Rental Home - 5 Bathrooms, Sleeps 10
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    Island Sunrise1 / 13
    (1)Very good
    Studio, 3 Bathrooms, Sleeps 8 Quick View
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    Island Sunrise is gorgeous 3 bedroom, 2.5 bathroom duplex home located in desirable Piney Island. Not only is this house pet friendly but it offers a deep water boat dock and 3 spacious decks. The views of Assateague Island and the Assateague Channel truly are second to none! Additional amenities...
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    ***6422 Church Street*** Enjoy all that downtown has to offer in this cozy island home within walking distance to shops and restaurants. There is plenty of privacy in this petite home! First floor bedroom features a table and Tv, great for hanging out playing games or watching movies while others...
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    Chincoteague Island, Virginia 23336
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    ***5104 Blake Point Road****Goose Bay tucked away off the northern end of Main Street offers a tranquil and serene location with outstanding waterviews and sunsets over the Chincoteague Bay and ponds. First Floor bedroom and two additional bedrooms with lof/sitting areat on second level. Very...
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Studio, 3 Bathrooms, Sleeps 6 Quick View
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    Looking for a clean, comfortable spot that's conveniently located? It's here at Eastwinds! This 2 bedroom townhome features an open floor plan downstairs, and 2 bedrooms/2 full bathrooms upstairs. You're just a few minutes from downtown - restaurants, shopping, movie theater and more. And,...
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bathrooms, Sleeps 6
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    Studio, 2 Bathrooms, Sleeps 8 Quick View
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    This lovely vacation rental home features 3 bedrooms and 2 bathrooms, including a 1st floor master suite with a queen bed. Blissful Way is very bright and airy with a large living room/Dining Area. Off of the kitchen is a screened porch great for family bar-b-ques. Upstairs you'll find two more...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bathrooms, Sleeps 8
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    Stormbreak1 / 21
    (3)Very good
    Studio, 2 Bathrooms, Sleeps 6 Quick View
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    Historic 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 with sliding windows allows for room to spread out in any...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    ***6314 Cropper Street***Lovely renovated 3 story Victorian combines classic charm with affordable luxury located in the heart of downtown Chincoteague.***Bed Sizes: 2 Queen, 2 Twin***Prime Season Rates: $1000 weekly/$200 per night.Off Season Rates: $800 weekly/$160 per night. Additional amenities...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Studio, 2 Bathrooms, Sleeps 7 Quick View
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    As a classic Chincoteague-style home, Hopkin's House is situated on the East Side of Chincoteague Island and overlooks the Assateague Channel. You'll enjoy a wonderful, relaxing vacation at this 3 bedroom home; it's just a short distance from the public boat ramp, Memorial Park, a restaurant and...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bathrooms, Sleeps 7
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    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
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    ***6153 Marsh Island Drive-Marsh Island*** The owners of this new vacation rental have taken special care to provide their guests with many extras, including 1 person kayaks, beach items and a crab pot for your use. The view looking across Chincoteague Channel to Reed Memorial Park is...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    Studio, 4 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Prospect Point offers one of the BEST locations on Chincoteague Island. Situated on the last lot at the northern-most tip of the island. This house boasts views of nothing but protected conservation land and open water. There are two bedrooms on the first level and two bedrooms on the second level....
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Shared Outdoor Pool (Unheated)
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    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    ***7134 Silver Sails Landing***Beautiful spacious duplex with all new furnishings. Screened porch overlooking the wetlands. Deck and community pool. Offers wireless internet!! Close to carnival grounds!***Bed Sizes: 2 Queen, 2 Twin, 1 Queen Sleep Sofa.***Prime Season Rates: $1350 weekly/$270 per...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Marsh Point1 / 13
    (3)Excellent
    Studio, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Wonderful 2 bedroom townhome that features a great screened porch off the living room, large bedrooms (including master bedroom suite) and second-level screened porch off one bedroom. Full ensemble of appliances, central air, water access, private pier (shared by other units), and more! New...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bathrooms, Sleeps 8
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    Studio, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bayside II is a nearly new, well appointed, waterview, 3-bedroom duplex located just off of South Main St. on the quiet southern end of the island. This spacious, nearly 2,000 sq ft. home offers a family of up to 8 an open floor plan to enjoy the whole gang without being cramped into a small area....
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bathrooms, Sleeps 8
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    La Puesta Del Sol1 / 19
    (1)Excellent
    Studio, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
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    Beautiful 3 bedroom, 2.5 bathroom waterfront townhome on Chincoteague Bay. Master bedroom suite with private bath. Screened porch overlooking bay. Long pier, great for fishing & crabbing. All amenities including wireless internet, all appliances and central air. Home sleeps 10. Additional...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bathrooms, Sleeps 10
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    Serenity Place1 / 12
    (1)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    ***5387 Hibiscus Drive-Oyster Bay I***Spend your day at the beach or on this wonderful wrap around screen porch. Canal front, located in private community.***Bed Sizes: 1 King, 2 Twin, 1 Trundle***Prime Season Rates: $1050 weekly/$210 per night.Off Season Rates: $800 weekly/$160 per night....
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    ***6444 Dogwood Lane*** Very nice and spacious home in quiet area of island. Large kitchen with stanless steel applicances, big dining area leads out to sun porch.***Bed Sizes: 2 Queen, 2 Twin***Prime Season Rates: $900 weekly/$180 per night.Off Season Rates: $775 weekly/$155 Per night....
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Assateague Light1 / 11
    (1)Very good
    Studio, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
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    This modern 2 bedroom condo located on the first floor features a master bedroom suite with a king bed, private bath and sliding glass door to the waterfront deck. The second bedroom has two twin beds with a full bathroom across the hall. This shared bath offers a walk in shower and washer/dryer....
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    Location Information
    Chincoteague Island, Virginia 23336
    Condo/Apartment - 2 Bathrooms, Sleeps 6
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    Studio, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This wonderful house is located on the edge of the Intercoastal Waterway/Chincoteague Bay, offering deep water access and breathtaking sunsets! Fish and dock your boat at your back door. Conveniently located, Lewis Creek House is just a short distance from the downtown area including shopping,...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bathrooms, Sleeps 6
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    Studio, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Air Conditioning
    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautifully renovated 4 bedroom, 2 bathroom home could be the ideal vacation home for your family and/or friends. Located on Oak Dr in Piney Island this home is an easy bike riding distance to the beach and trails of Assateague Island. Aramabad has a completely renovated kitchen with granite...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bathrooms, Sleeps 8
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