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Villas in Chincoteague Island

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    Travellers to Chincoteague Island are booking August dates now. Secure your holiday rental today, and have the perfect trip.
    All 323 Rentals in Chincoteague Island
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    La Puesta Del Sol1 / 19
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Luxury water view vacation rental home with dock access. This home boasts a full ensemble of amenities and the most beautiful views of Assateague Island. The chef's kitchen compliments the spacious dining area that opens up to the large screened porch. Beautiful custom windows and large sliding...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Nestled beneath the tall pines is where you'll find this delightful Piney Island home. The Bird House features an open living room/kitchen/dining area, and extra "family" space in the private den. The many large windows throughout the home create a bright, airy atmosphere. Enjoy relaxing breezes on...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    ***5392 Sunrise Drive-Oyster Bay I***Newly remodeled in 2014 now with an open floor plan and expanded rooms! The renovated kitchen in this Oyster Bay waterfront home will inspire cooks and the new dining room is terrific for family gatherings. There is lots of new decking and when you're not at...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Rest and relax at the charming Carriage House while enjoying all of the modern conveniences of home. Built in a quiet community (Oyster Bay II), this home features a large and spacious kitchen, with an open concept living room and dining room. Plenty of sleeping space with a 1st floor master...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Comfortable, pet friendly home on large, private side-creek lot with fantastic views from both front and back of house! Excellent crabbing from dock! (Property sits on creek only suitable for kayaks, canoes and crabbing.) Easy walking distance to Memorial Park and Fairgrounds. 2 living areas, 2...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Conch Shell1 / 14
    (2)Very good
    3 Bedrooms, 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
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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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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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    A beautiful ground-floor villa with walk out to marina. Luxurious master bedroom with private bath includes both a roomy tiled shower and whirlpool bath. Villa 116 will sleep 8, and includes a full laundry, all appliances, a gourmet kitchen more. There's a pool and fitness room for your enjoyment....
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    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Return1 / 34
    (2)Average
    4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    Beautiful waterfront contemporary perched on the edge of Assateague Channel. Enjoy breathtaking vistas of Assateague Island, the lighthouse, the wild ponies and the abundant wildlife. This spacious home boasts a complete line of amenities including a 600' pier/dock with deep water access (17'), and...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 11
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Great White1 / 23
    (5)Very good
    5 Bedrooms, 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
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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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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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    All fresh, brand new, and waiting for you! You won't believe the NEW Nautilus! The new owners have taken great pleasure and pride in making this fabulous beach home everything that it is today. Enjoy the open floor plan inside that offers water views from nearly every room. There's also a dock with...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Aptly named, 'Peace Smuggler' will help you reclaim the peace and serenity you are looking for. A fabulous home with a unique floor plan - all situated along the natural marshes of the Chincoteague Bay. Featuring 4 bedrooms, large open main living spaces and all the modern amenities, this may be...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Sunset Bay Villa 3191 / 18
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Beautiful Villa 319 offers a premier location with all amenities. This top floor corner villa is spacious and accommodating, featuring 3 bedrooms. The master bedroom suite has a private luxury bath for your enjoyment and a private entrance to the waterside balcony. Enjoy romantic sunsets on...
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    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
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    Pet friendly
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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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
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    ***7235 Bunting***Very nice mobile home in private setting with large enclosed porch overlooking the marsh. Close to town harbour and offers all amenities including internet. All bedroom on the same level***Bed Sizes: 1 Queen, 1 Twin, 1 Bunk (2 Twins), 1 Bunk (1 Twin & 1 Double)***Rates:Prime...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Red Cedar1 / 16
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Nature calls at this nicely appointed 3 bedroom rental home. Red Cedar is nestled on the edge of a huge expanse of nature preserve-type land where you'll see all types of native wildlife. Birders bring your life list. The home features modern amenities, offers a first floor bedroom, full laundry,...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Edie's Folly1 / 20
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    ***6404 Pine Drive-Piney Island***Nature lover’s dream! Tucked away in Piney Island with Assateague just a short bike ride away . You’ll love relaxing in the large screen porch or enjoy the water views from the second level deck. Community boat launch great for kayakers. Sleeps 9, screen porch, 2...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Cockleshell Cottage1 / 14
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Nestled on a quiet cul-de-sac in a private community just off North Main Street (Oyster Bay II) is where you'll find the charming Cockleshell Cottage. This new 3 bedroom, 3 bathroom home boasts a first-floor master bedroom suite, all modern amenities and new furnishings. It is handlcap accessible....
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    ***5169 Winder Lane***This waterfront 4 bedroom, pet friendly home is tucked away off North Main Street. Watch the sunset from the large screened porch. Offers fenced yard, well stocked kitchen, dinign room and a spacious living room. Upstairs has master suite with private bath, 2 bedrooms and a...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Chincoteague Charm1 / 25
    (3)Average
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Chincoteague Charm is a beautiful home located on North Main Street. It's just across the street from Chincoteague Bay and there is water access to the bay for kayaks & canoes. The home is very tastefully furnished, has a great kitchen/dining area with center island and quality stainless steel...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    June's Retreat1 / 33
    (1)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Grill
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    June’s Retreat is Chincoteague Island’s premier luxury vacation rental home, nestled on serene waterfront marshlands just north of town off of Main Street. This custom designed and decorated home leaves no detail unnoticed. From the bright spacious rooms with floor-to-ceiling windows to the...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    Misty Manor1 / 11
    (1)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    ****8118 Leo Lane****This bright and cheerful home is tucked away on a private lane next to Misty's Pony Farm. It offers first floor bedroom and bath. Close to Summer Memories.*** Now offering WiFi.This Property accepts pets under 40lbs Only***Bed Sizes: 1 Queen, 1 Double, 1 Set of Bunks, 1...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Southern Exposure is nestled along the natural shoreline of Little Oyster Bay, offering some of the most beautiful water views on Chincoteague Island. Conveniently located in one of Chincoteague's most popular residential communities, you're only minutes from the beach and attractions - shopping,...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    ***7541 Pony Cove Lane***Comfortable duplex with screen porch is a delight. Next to Seagull's in Flight. WiFi in the prime season.***Bed Sizes: 1 King, 1 Queen, 4 Twin, 1 Double Sleep Sofa, & 1 Twin Day Bed***Prime Season Rates: $950 weekly/$190 per night.Off Season Rates: $650 weekly/$130 per...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    ***3584 Willow Street***Pet Friendly.Charming restored island home will make you smile! Relax in the screened porch after a day at the beach. Close to everything! A Short walk to the carnival and historic downtown with shops and restarurants. Large yard, perfect for children and pets. Close by...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Beautiful 3 Bedroom, 2 bath single family home located in Piney Island - the closest community to the beach! Downstairs you'll find an open kitchen and dining area, living room, 2 bedrooms (with twin beds), a bathroom, and a large screen porch. Perfect for enjoying meals outside in the breeze! The...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Snowy Egret1 / 14
    (1)Average
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Light, bright & airy, Snowy Egret is a wonderfully large vacation home that boasts a full ensemble of amenities along with a nice waterfront setting. Downstairs you'll find a large living/dining room combo and a nice modern kitchen. Off the kitchen is a private den area (futon) - a perfect spot to...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Very nice waterfront home overlooking Assateague Island and lighthouse. Satellite TV, all amenities. Nice waterside deck areas. Long pier and dock (deep water) shared with house next door. New waterside screened porch and upper level balcony. Relax and chill out after a long day at the beach. Close...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Abbie Thornton Cottage1 / 19
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    This charming Chincoteague cottage was built in the 1930's and is located directly across the street from the Chincoteague Bay. Abbie Thornton Cottage has kept much of the original integrity, but has been lovingly restored to offer all the modern comforts of home. There's a cozy screened porch off...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Sunset Bay Villa 1091 / 20
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
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    This beautiful ground-level villa boasts five-star amenities including a private deck off the living room area with a walk-out to the marina. Enjoy this master bedroom suite, with private bath that features a jetted tub to relax in and a private exit to the waterside deck area. The gourmet kitchen...
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    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Blue Heron1 / 19
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    This modern beach retreat features an open floor plan, perfect for socializing with friends or just relaxing after a fun day at the beach. It is located on Oak Drive on Piney Island, closest neighborhood to the beach and convenient for shopping and dining on Maddox Blvd. A few of the amenities...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Sea Gulls in Flight1 / 10
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    ***7531 Pony Cove Lane***This is an immaculate, tucked away duplex for very quiet and peaceful setting. It offers a large sun porch,and back yard. Will be a 10 x 22 screen porch will be added for the 2010 rental season.***Bed Sizes: 2 Queen, 1Twin Day Bed w/Trundle, 1 Queen Sleep Sofa ***Prime...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Charming home located on South Main Street. Large screened porch on the front of the house - you'll enjoy relaxing while watching the sun set at night. The large 3 bedroom home boast all amenities, including central air, washer/dryer, screened porch, outside shower and more. ** SPECIAL NOTE: Miss...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sunset Bay Villa 3121 / 16
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Villa 312 is a beautiful 3 bedroom villa featuring a master bedroom suite with luxury bath, gourmet kitchen with center island which is great for entertaining, laundry room with washer/dryer and a waterside balcony overlooking Chincoteague Bay. There are tvs in all the bedrooms, and a computer desk...
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    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sand Dollar1 / 15
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    This very nice 3 bedroom home is located in Piney Island - just a short distance to Assateague Island. The home boasts all amenities including a fully equipped kitchen with all appliances, washer/dryer, central air, outside h/c shower, screened porch, plenty of parking. The open floor plan and...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Back by popular demand, Channel Point is a charming example of a historic shingle-covered Chincoteague Island Waterman's Cottage. Located at the point where the Chincoteague Channel meets the Chincoteague Bay, you'll enjoy breathtaking sunset views from the screened porch or the open second level...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
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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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    We cannot say enough about this delightful beach home! Located in popular Oyster Bay I private community, you'll enjoy the serene waterfront location. Featuring 3 bedrooms, 2 bathrooms and all modern amenities, a wonderful vacation awaits you at 'Smooth Sailing'! Additional amenities include:...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cowboy Cottage1 / 13
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Cowboy Cottage is a pet friendly home conveniently located a block from Maddox Blvd and just a couple of blocks from downtown Main St. 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 screened...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    ***6317 Highland Park Drive***Bring your kayaks and kids! This is a bright tastefully decorated rancher! Playset in backyard for small children, located in quiet neighborhood and in walking distance of restaurants and attractions. All bedrooms on the same level.***Bed Sizes: 1 Queen, 1 Double, 2...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Charming in-town 3 bedroom home with a day-bed alcove, 2 baths, large fenced yard, carport and screened porch. Located on a quiet street, but a short walk to downtown shopping, movies and restaurants. Expanded Master Bedroom with claw foot tub and king size bed. Amenities also include outside...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Assateague Breeze1 / 17
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    ****5466 Amrien Circle****You won't believe the outstanding views of Assateague Island with this lovely 3 Bedrooms, 2 Bathrooms, contemporary home. Lovely marsh to the back, this home has location going on. Large, open and bright great room leads out to deck and porch. Living room with gas...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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