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Villas in Chincoteague Island

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    Travellers to Chincoteague Island are booking April dates now. Secure your holiday rental today, and have the perfect trip.
    All 308 Rentals in Chincoteague Island
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Panorama1 / 9
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Tastefully appointed gem situated on the Assateague Channel. Enjoy the unobstructed views of the channel and Assateague Lighthouse! Master bedroom suite with doors to waterside deck area, screened porch, open floor plan and more. Tastefully furnished, this is a great unit! Two parking spaces...
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    Chincoteague Island, Virginia 23336
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
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    Looking for a fun place for a family vacation? Look no further! Blue Diamond offers all amenities: community pool, shared water access, comfortable furnishings and high speed internet (just to name a few). And if that's not enough, Blue Diamond is located on the popular East Side of the island...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    About this property
    This delightful townhome features beach living at it's best. The Master Bedroom offers a private balcony with sunset views. Snow goose also offers (shared) dock access to a tidal canal that is full of wildlife. Additional amenities include: sight seeing, view: water access, laundry: washer &...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Sunset Bay Villa 1111 / 14
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    This 3 bedroom 2 bathroom luxury villa features a first floor, open floor plan villa for easy access, and it is dog friendly! The first bedroom offers a twin trundle bed, the second bedroom has a queen bed, and master suite has a queen bed with a private bathroom and access to the waterfront deck....
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    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    The Bonnie Blue1 / 8
    (1)Terrible
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    ***7065 Wayne Road***Spacious rancher is pet friendly with large deck, fenced yard and internet.***Bed Sizes: 1 Queen, 1 Double, 1 Twin, 1 Double Sleep Sofa***2018 Rates:Prime Season Rates: $800 weekly/$160 per night.Off Season Rates: $650 weekly/$130 per night.Shoulder Season: $725 weekly/$145...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tall Pines1 / 8
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Located in lovely Piney Island within a short bike ride to the beach. This single story 2 bedroom, 1.5 bathroom house offers a large screened porch, fully equipped kitchen and spacious living room. Piney Island offers community water access great for launching kayaks/canoes. To top it all off, Tall...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    ***6303 Chester Park*****Well appointed home located in quiet neighborhood offers first floor bedroom and bath. Offers internet access!***Bed Sizes: 2 Queen, 2 Sets of Bunks(1 Twin & 1 Double on each), 1 Queen Sleep Sofa***Prime Season Rate: $975 weekly/$195 per night.Off Season Rates: $625...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Sundance1 / 15
    (3)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Light, bright and airy - this beautiful home is very well maintained, tastefully furnished and boasts all amenities including screened porch, outside shower, all appliances including washer/dryer, tvs in every bedroom and more. The home is located just outside of town and offers a very quiet...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    Island Sunrise1 / 13
    (2)Very good
    3 Bedrooms, 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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    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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    ***3402 Ridge Road***Lovely 2 Bedrooms, 1.5 Baths duplex with water views. This duplex overlooks Assateague Island with great views for the Pony Swim. This is the Best way to watch the Pony Swim and not move from your porch! Sit and enjoy the views from 2 porches. The screened porch is off of the...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Very nice waterfront condo unit overlooking Assateague Island. Ground floor unit. This unit will sleep 4, and comes with a deep water boat slip for your use all week. Fish or crab from the dock. There is a community laundry facility on premises. The condo is conveniently located right next door to...
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    Chincoteague Island, Virginia 23336
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    Do you need a vacation rental where you can park your boat and bring your pet? You've found it! Sea Tag #23 is a great two bedroom unit (upper level) that overlooks beautiful Assateague Island. Enjoy relaxing on the covered porch after a fantastic day of fishing. The views of Assateague are...
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    Chincoteague Island, Virginia 23336
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
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    Pet friendly
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    Smoking allowed
    About this property
    Homeport is a comfortable, inviting, 2 bedroom, 1 bathroom, centrally air conditioned home located on a quiet street within a short walk to town. Upon entering the home you are greeted by a large living room with a queen sleeper sofa, and a kitchen that opens onto the back deck and screen porch....
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Lighthouse View Townhouse1 / 15
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Lighthouse View is located on the east side of our ialnd and includes a private community pool for your enjoyment. The 3 bedroom, 2 bath townhouse features two first floor bedrooms with full bath in the hallway and a master bedroom suite upstairs. There's water access across the street with a...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 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***2017 Off Season Rates: $650 weekly/$130 per night.2018Prime Seaosn Rates: $950...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    ***4446 Main Street****Pet Friendly. Proud traditional with a water view of the Chincoteague Bay. Large appointed rooms, back deck and front screened porch.***Bed Sizes: 2 Queen, 2 Twin, 1 Double***Prime Season Rates: $875 weekly/$175 per night.Off Season Rates: $650 weekly/$130 per night.Shoulder...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Chincoteague Charm1 / 25
    (3)Average
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    About this property
    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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    Shady Side1 / 14
    (4)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Shady Side is located in Piney Island, which is among the closest communities to the beach. It is also a short bike ride to the trails and beach at Assateague. There is a private boat launch in the community for your boat, kayak, or canoe. The house features two queen bedrooms (both with new...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    ***6321 Captain's Lane Unit #107 Sunset Bay Villas***Beats Campin in a total luxury Waterfront Condo, first floor unit overlooks Marina and Chincoteague Bay. Master Bedroom with jacuzzi tub and large waterfront balcony off the spacious living area. Fully equipped with all amenities. Internet...
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    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sunset Bay Villa 3121 / 16
    (3)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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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    ***4265 Pension Street***Charming, traditional island home near town. Walking distance to shops, restaurants, and waterfront. Perfect for gathering family/friends!! Near Cattail Cottage, Miss Niccies, Time Out, Cool Shack and Rhinos Retreat. 4 bedrooms upstairs/2 baths downstairs.***Bed Sizes: 1...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Stingray1 / 15
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Luxurious 2nd-level waterfront condo with views you won't believe! Tastefully decorated with work of local artisans, features all amenities, as well as master bedroom suite with king bed & waterside balcony. Many extras like a flat screen TV and a Lazy Boy leather recliner. The open floor plan is...
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    Chincoteague Island, Virginia 23336
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Vanity Fair1 / 13
    (1)Excellent
    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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Paradise View1 / 44
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Truly a masterpiece, this luxury vacation rental home offers only the finest amenities. Each bedroom is a separate suite with private bath. The master bedroom suite (K) features two a spa bath with jetted tub, a private waterside deck area and beautiful water views. To capture the best views,...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    ***3849 Main Street***Charming and spacious island home offering a first floor bedroom and Outside Shower. Close to center of town, near restaurants, shopping and nightly entertainment.***1 Bedroom & 1Bath downstairs/3 Bedrooms & 1 Bath-2nd floor/1 Bedroom-3rd floor***20 Foot Boat slip rentals...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Smoking allowed
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    This wonderful 3 bedroom, 2.5 bath rental home is light, bright & airy. Adam's Apple boasts all amenities including community pool privileges, 1st floor master, open floor plan, screened porch, deck, fully stocked kitchen & more. Adam's Apple is located in a nice, natural setting not too far from...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Great 2 bedroom, 2.5 bath townhome in Lighthouse Estates community off East Side Drive. This home features all amenities including central air, washer/dryer and new kitchen appliances. In addition, there is a community pool as well as water access and a dock (shared) to fish and crab from. This is...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Misty's Thicket1 / 13
    (2)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Lovely townhome rental features TWO great screened porches! One with a ceiling fan just off living room, large bedrooms, including a master bedroom suite, second-level screened porch off one bedroom and an outside shower. A full ensemble of appliances, central air, galley-style kitchen, water...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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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 the Assateague Channel, 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 -...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    ***7460 Pony Swim Lane***Waterfront duplex with deep water dock and great views of Assateague Island and Lighthouse. Newly remodeled kitchen, living room, and dining room. Now offers wireless interenet. 2 bedrooms and 1 bath upstairs, 1 bath downstairs.*** Bed Sizes: 1 Queen, 4 Twin***Rates:...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    This great contemporary beach home is located at the edge of the community harbor area, a perfect location for you and your guests. As a pet friendly house, you'll enjoy the wide open spaces for your dogs. The 3BR/2BA home features an open floor plan with lovely eat-in kitchen and cook area that is...
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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 7 Quick View
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    Come and check out the new 'Channel Watch'! Beautiful waterfront duplex in a secluded area on Piney Island just minutes from the beach! Features include a waterside screened porch (accessible from the main living area and master bedroom suite), central heat/air, private pier, 2 master bedroom...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    What a beautiful home! This classic downtown Victorian is perfect for your vacation. The spacious first floor offers a large living room, formal dining room, fully equipped kitchen screened porch and queen bedroom plus half bath. Upstairs you'll be welcomed by two large bedrooms one Master Suite...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Lighthouse Pointe1 / 15
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    One of East Side's most popular rentals! Features include open floor plan with waterside balcony downstairs, and a spacious third level master bedroom suite with private waterside balcony. All levels have balconies or deck! Very conveniently located - close to Memorial Park, restaurants and marina....
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Island Thyme1 / 14
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    There's plenty of room for everyone here at Island Thyme! This spacious home features a living room and den, large eat-in kitchen and dining area, and a huge wrap-around deck -- perfect for enjoying the quiet, peaceful setting. The many extras include a hot tub (on back deck), and Foosball table....
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Admiral Benbow1 / 10
    (1)Excellent
    3 Bedrooms, 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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Sunset Bay Villa 2211 / 13
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    COME AND ENJOY! You've earned it. Located on the edge of beautiful Chincoteague Bay, Sunset Bay Villa 221 is a luxury waterfront condominium that sleeps 8 with three rooms for sleeping. This unit boasts over 1,700 square feet of luxury living space with all amenities - waterfront balcony, master...
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    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    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.***Rates:Prime Season Rates: $1350 weekly/$270 per night.Off Season...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    • Balcony
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    Pet friendly
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    Smoking allowed
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    ***7136 Silver Sails Landing***Spacious duplex overlooking the wetlands. With screen porch, deck, first floor master suite, enjoy the community pool after a long day at the beach! Next door to Bay Pony.***Bed Sizes: 2 King, 2 Twin***Prime Season Rates: $1350 weekly/$270 per night.Off Season Rates:...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Serendipity1 / 14
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Come stay in this classic Eastern Shore Style home. Located just a few blocks from our famous downtown Main Street area, you are within walking distance to most of our shops and restaurants. Serendipity has a very nice screened porch for those memorable Chincoteague Summer evenings. This home also...
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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 6 Quick View
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    We are pleased to be able to offer Quackers within our inventory of distinctive rental properties. This 3BR/2 bath contemporary ranch has all the bells and whistles - a lovely screened porch, a grilling deck, a luxurious master bedroom suite with private bath and internet access. The quiet setting...
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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 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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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sand Dollar1 / 14
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    ***7142 Pine Drive-Piney Island***Lovely home in Piney Island offers views of Assateague Island and water access. Perfect for a large family. Community boat launch area great for kayakers. Within walking distance to Assateague and Water Park***Also offering Internet connected Blu-Ray player***Bed...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Assateague Light1 / 11
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    About this property
    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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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Tastefully remodeled beach home featuring a reverse floor plan and spectacular views of the Assateague Channel and Lighthouse! Located on the popular East Side of Chincoteague Island, Channel View is conveniently located near a public boat ramp, restaurants and Memorial Park. And you're about a...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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