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Holiday Rentals and Villas in Chincoteague Island, VA

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    Travellers to Chincoteague Island are booking October dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 31
    4.5 of 5 stars (5) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 12
    5 of 5 stars (7) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    1 / 19
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 21
    5 of 5 stars (30) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This historic Waterman's Cottage , circa 1920, located on Chincoteague Island, has been beautifully restored and is a perfect family vacation spot. We are across the street from the Chincoteague Bay and 1 mile to the center of town.The house has a large eat-in-kitchen, family room as well as a... View all property information
    Location Information
    Chincoteague Island, Virginia
    5 of 5 stars Reviewed 4 weeks ago
    Quaint, comfortable with several reading nooks & whimsy in unexpected places. Owners very nice & easily accessible. Games, wifi, tv, etc available though we spent so much time...
    5 of 5 stars Reviewed 18 August 2016
    Staying here felt like visiting a friend's house. It was thoughtfully and whimsically decorated, clean and comfy. My favorite features were the outdoor shower; the screened front...
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    1 / 15
    5 of 5 stars (2) Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Come stay and relax at this quiet retreat. This listing is a newly remodeled home which is tastefully decorated. There are three color themed bedroom's; which have two queens and two twin sized beds. There is serenity all around you, come sit on the screened in porch and relax while listening to... View all property information
    Location Information
    Chincoteague Island, Virginia
    5 of 5 stars Reviewed 4 May 2015
    This house isn't super fancy - it's just right. This retreat fits the spirit of Chincoteague Island. It is tastefully and simply decorated, nice paint colors - calming, peaceful...
    5 of 5 stars Reviewed 1 October 2014
    This rental is located close to Main Street, and was perfect for my husband, my mom, and I. Although we visited during the off-season and most the of the businesses on Main Street...
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    1 / 16
    5 of 5 stars (4) Excellent
    2 Bedrooms, 4 Bathrooms, Sleeps 15 | Quick View
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    About this property
    Fresh redo on this spacious and comfortable home, new carpet, flooring, furnishings, mattresses, granite counter tops, tile work and more !<BR> This house has extensive accomadations, two and a half bathrooms and an outdoor shower and foot washing station make as well as a private outdoor hot tub... View all property information
    Location Information
    Chincoteague Island, Virginia
    5 of 5 stars Reviewed 22 July 2016
    This was our 2nd year . this house is perfect for a large family vacation tim and Collen keep this clean and have a well stock kitchen every thing you need is there house is large...
    5 of 5 stars Reviewed 31 August 2015
    We have been visiting Chincoteague for over 40 years. We have rented many houses on the island but this home is truly a home away from home. This was our first time using VRBO...
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    1 / 12
    4 of 5 stars (1) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Private Garden
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    About this property
    Cute, colorful 2 bedroom cottage with front and back porches. Walking distance to charming old town Main Street shops and restaurants. Back yard with grill and picnic table. Outside shower. Have coffee on the sunny back porch overlooking private back yard. Lots of windows. Wifi. DVDs for... View all property information
    Location Information
    Chincoteague Island, Virginia
    4 of 5 stars Reviewed 4 weeks ago
    Good: - Clean, comfortable and functional - Location walkable to Main St shops and a bowling alley - Window air conditioners worked well Could be improved: - Owner's...
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    1 / 13
    4.5 of 5 stars (4) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Totally updated but traditional "home away from home" facing the Chincoteague Channel on Chincoteague Island, minutes from the quaint downtown and the Assateague National Seashore and Wildlife refuge. Relax in this spacious, clean, and beautifully furnished home with water views of the sunset from... View all property information
    Location Information
    Chincoteague Island, Virginia
    5 of 5 stars Reviewed 4 weeks ago
    We rented this house for a week in August. Our extended family included myself, my husband, my two teenagers, and my mother and stepfather. The house (four bedrooms) had plenty of...
    4 of 5 stars Reviewed 14 August 2014
    We were pleasantly surprised at how much we enjoyed staying in this rental. We usually stay on the other side of the island. We were worried about it being one of the older homes...
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    1 / 10
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Situated on the intracoastal waterway, this unique waterfront cottage is a location sensation. The home was originally part of the community of Assateague, and later was relocated to the island of Chincoteague. The great room boasts vaulted ceilings, wrap around windows/doors with remote controlled... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 20
    5 of 5 stars (37) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Air Conditioning
    • Grill
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    • Patio
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    • Pet-friendly
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    About this property
    Duck's Delight is our home in America's Happiest Seaside Town (2014 Coastal Living)! Entire home updated/renovated for the 2015 booking season! 4 bedroom (3 queen sized beds and 2 sets of bunkbeds), 2 bath Cape Cod in Chincoteague, VA., home of the Assateague ponies. Small fishing town on the... View all property information
    Location Information
    Chincoteague Island, Virginia
    5 of 5 stars Reviewed 26 May 2016
    This was the perfect house for two families to spend some time together. We were able to walk almost everywhere that we went and we rented bikes for the kids and they had the...
    5 of 5 stars Reviewed 11 April 2016
    I and my family have been renting this house for years. I love this house! - It is always neat, clean and you can't ask for a better location. The location is great! You can...
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    1 / 14
    2 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    ** 4410 Eastwinds ** New to the vacation rental market! Tastefully remodeled and decorated, 'Gone Coastal' is the perfect motto for this beach getaway! Located close to downtown - movies, shopping, restaurants and more. And you're only about 2 miles to the entrance to the beach! This rental... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 19
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    This is a Charming Victorian cottage is located at 5020 Main Street. Enjoy a beautiful pond, garden and water views. This is a perfect getaway for couples. The master bedroom has a queen bed and a cozy sitting area. Enjoy many amenities such as a screened porch, dishwasher, microwave, washer/dryer,... View all property information
    Location Information
    Chincoteague Island, Virginia
    5 of 5 stars Reviewed 25 August 2015
    My husband and I stayed at Abbie Thornton cottage in August 2015 and are SO happy we booked this place! It was absolutely wonderful, from the screened in porch (perfect spot for...
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    1 / 29
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    ** 3386 Hook Drive ** Comfortable pet-friendly home on large, private creek-side lot. There are fantastic views from the front and back of house and tons of wildlife and birds. It is within walking distance to Memorial Park and the Fairgrounds. The home features a dock on a creek perfect for... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 16
    4.5 of 5 stars (2) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
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    • ?
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    3420 Ridge Road. * A very nice waterview townhome overlooking Assateague Island and the lighthouse. Located across the street from "Mr. Baldy's Restaurant" formerly known as Island Family Restaurant and in walking distance to Memorial Park park (where there is a boat ramp, a fishing pier, and... View all property information
    Location Information
    Chincoteague Island, Virginia
    4 of 5 stars Reviewed 4 April 2016
    We had a great time at the vacation house. The house was as expected and nicely decorated. The beds were a little hard but the view was beautiful and made up for it. We stayed...
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    1 / 32
    5 of 5 stars (2) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Washer
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    • Satellite TV
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Sand and Sea-renity is a Newly Listed, "Brand New", charming, calming, and relaxing, 4 bedroom, 3 and a half bath, central air conditioned home, that sleeps up to 8 people with 3 queen, and one day bed that can be used as 2 Twins or 1 King. Tucked away at the end of a quiet cul-de-sac in Oyster Bay... View all property information
    Location Information
    Chincoteague Island, Virginia
    5 of 5 stars Reviewed 28 June 2016
    Truly lived up to its name. Very peaceful area with wonderful water views. Close to town and island attractions. Nicely furnished and well equipped. Traveled with a party of...
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    1 / 7
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Shared Outdoor Pool...
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    ** 6321 Captian's Lane, Unit 110 ** Located on the edge of beautiful Chincoteague Bay, Sunset Bay Villas are distinctive condominium homes that offer nothing less than the finest amenities. This unit boasts over 1,700 square feet of living space with 3 bedrooms, spacious waterfront balcony, private... View all property information
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    Chincoteague Island, Virginia
    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    About this property
    This home is located at 7452 Memorial Park Drive. Located right next to Memorial Park! Enjoy fantastic water views from your deck and all the amenities Memorial Park offers; picnic areas, fishing dock, boat ramp & more. This great 2 bedroom home offers a queen bed, 2 twin beds, and a sleeper sofa.... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 16
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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    • x
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    About this property
    This is a lovely 2 bedroom townhome with gorgeous water views of the Assateague Island. This home will accommodate up to 6. There is a queen sized bed, a double sized bed, and 2 twin sized beds. This home features a full line of appliances including an washer/dryer, a dishwasher, central air, and... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 12
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Pet-friendly
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    • x
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    8152 Marsh Point Lane. **This lovely vacation rental home features 3BR/2BA (2Q/D/T), central air, screened porch, out door shower (hot & cold) and a nice open floor plan. There is a full line of amenities including central air, all appliances and washer/dryer. There is also WIRELESS INTERNET... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 25
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    6254 Wagner Lane.** This beautiful 2BR ranch home has a quiet, out-of-the-way location on Little Oyster Bay. The views of the bay are beautiful. And there's a long pier and dock. It's perfect for crabbing, kayaking & canoeing. An Unfettered View features all amenities including a private master... View all property information
    Location Information
    Chincoteague Island, Virginia
    5 of 5 stars Reviewed 2 weeks ago
    This place is absolutely EVERYTHING you could hope for on vacation. The home is immaculately clean and lots of room. The well-kept , private dock is an exciting and successful...
    5 of 5 stars Reviewed 28 September 2015
    An Unfettered View felt like home away from home. The house is very comfortable and offers a beautiful view of Little Oyster Bay. It was super-clean and well maintained. We found...
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    1 / 27
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Ocean Views
    • Satellite TV
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    • Waterfront
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    • Pet-friendly
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    • x
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    • x
    About this property
    SEA HARBOR: 1 mile from Assateague Island and 5 miles from beach front fun. Check-In 4pm Check-Out 12pm. This home offers large open spaces, a cozy, clean and comfortable place to stay along with amazing adventures for everyone to explore. It is furnished with many necessities so you can rest,... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 17
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Pet-friendly
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    • x
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    3050 Main Street.** Our Oasis - this very popular waterfront rental home on South Main Street offers breathtaking views over Chincoteague Bay and the most gorgeous sunsets ever. The spacious three bedroom home has all the bells and whistles -- a master bedroom suite (K) with private bath and... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    ** 7518 Doe Bay Lane ** A beautiful, nearly brand new 3 bedroom duplex home that offers great views of Chincoteague Bay and a great location on South Main Street. The home has been tastefully furnished with good quality, comfortable furniture that you'll enjoy. The three bedroom home has all the... View all property information
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    Chincoteague Island, Virginia
    1 / 35
    5 Bedrooms, 4 Bathrooms, Sleeps 11 | Quick View
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    • Grill
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    4653 Main Street.**. Tucked away off North Main on the waterfront, Lavinder House is a charming Victorian-style home steeped in tradition. From the original woodwork to the brick kitchen floor, you'll enjoy the original integrity this island home features. Once the home of actress Linda Lavin,... View all property information
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    Chincoteague Island, Virginia
    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
    • DVD Player
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    • Terrace
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    • x
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    About this property
    This is a very nice rental unit with views of Assateague Island and is located on 7452 Memorial Park Drive. The master bedroom has one queen bed. The second bedroom has 2 twin beds. There is also a queen sleeper sofa. This home is in a prime located. It is steps from the water and from Memorial... View all property information
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    Chincoteague Island, Virginia
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    **3914 Main Street.** Very nice 3 bedroom home sleeps 6. Full bath on each level (shower only on first level). The spacious living room has a great picture window overlooking Main Street. There's a separate dining room - a great space for gathering the gang for a meal! Bedrooms on both levels... View all property information
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    Chincoteague Island, Virginia
    1 / 11
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    Very nice waterfront condo unit overlooking Assateague Island located at 7482 East Side Drive. This unit is a ground floor unit. The master bedroom has 1 queen bed and the living room sofa turns into a queen sleeper sofa for extra guests. This home comes with a deep water boat slip for you to use... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 22
    5 of 5 stars (1) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • x
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    About this property
    7665 East Side Drive** We have added internet access! If you feel the need to stay connected, we are here for you. This home has it all - a community pool, a dock for fishing and crabbing, and even a beatiful master bedroom suite with jacuzzi tub! (3Q/ 1QSS). We are close to Memorial Park and... View all property information
    Location Information
    Chincoteague Island, Virginia
    5 of 5 stars Reviewed 28 June 2016
    Loved everything about this place! Location was perfect to Assateague Island and town. Our 13 year old twin grandchildren loved having big (queen-sizes) beds and own full...
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    1 / 15
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Light, bright & comfortable townhouse in Lighthouse Estates with pool privileges and water views, located at 7665 East Side Drive. There's water access across the street w/a boat dock. The boat dock is first come first serve. The bedrooms and bathrooms are on both levels. There is 2 queen beds, 2... View all property information
    Location Information
    Chincoteague Island, Virginia
    4 of 5 stars Reviewed 4 July 2016
    I enjoyed my stay in this home. My only complaint is that I initially inquired if there was a dishwasher prior to renting because it was not listed as an amenity. I was answered...
    5 of 5 stars Reviewed 7 April 2015
    We have stayed in this rental several times over the past 14 years. It is well furnished, has plenty of room, is beautifully decorated, and excellent for a large family!! The pool...
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    1 / 12
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    5373 Britton Lane. Bay Dreamer is a spacious 3 bedroom(2Q/1QSS/1futon/1Bunk-F/T) modern home with multiple porches and decks and spectacular sunset views, just minutes from downtown. This large three level home features a furnished rec room, open living and dining room with modern kitchen, large... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 18
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    7057 Pine Creek Dr.** Enjoy privacy and convenience in this happy home. The last house on the road nestled in a pine grove is both private and safe at the same time, close to the carnival grounds, pony pen, supermarket and main roads. The spacious 3 bedroom (2Q/ 2T/ 1 QSS) home will sleep 8 and... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 16
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    5405 Miflin's Marsh - Nature calls at this nicely appointed 3 bedroom rental home. The home 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... View all property information
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    Chincoteague Island, Virginia
    1 / 15
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    6313 Popular Street. A great three bedroom home (3Q, 1D) with a great 'in-town' location. Walk to movies, restaurants, shopping, etc. Agape House features many new upgrades including updated bathrooms, fresh paint, new carpeting & more. Master Bedroom suite features a whirlpool tub - so come... View all property information
    Location Information
    Chincoteague Island, Virginia
    5 of 5 stars Reviewed 3 June 2016
    We have been vacationing on Chincoteague for years and Love everything about it, This is a great house with lots of room we had two adults and four teens and it worked out...
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    2 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    4092 Grand Bay Court.** Family-Friendly, FUN -- This is a great rental home that features 2BR/2.5BA. (1Q/ 1D/ 1QSS/ 1 TRUNDLE) The home features all amenities including central air, washer/dryer, dishwasher and is located across the street from Memorial Park, Etta's... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 15
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Beautiful 3 bedroom home located in one of Chincoteague Island's private WATERFRONT communities called Oyster Bay! This home address is 5412 Coral Court. Snoozin' Goose offers an open floor plan with a large and bright rooms and modern amenities. This home is located in a quiet and peaceful... View all property information
    Location Information
    Chincoteague Island, Virginia
    5 of 5 stars Reviewed 19 April 2014
    We liked the open floor plan, five decks (!), and location in the pines next to a canal leading to Oyster Bay. The home is in a very nice development in a quiet location, The...
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    1 / 14
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    ** 7041 Pine Creek Drive ** 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... View all property information
    Location Information
    Chincoteague Island, Virginia
    5 of 5 stars Reviewed 16 July 2013
    I loved this property. This was the third time my family and I stayed at Island Thyme. The location is great, it's in the middle of the little town and less than half a mile from...
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    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    5397Oak Drive.** New to the Chincoteague vacation rental market. This very nice 3 bedroom home is located in Piney Island - just a short walk to Assateague Island. (1K/1Q/1F/T/1QSS). The home boasts all amenities including a fully equipped kitchen with all appliances & washer/dryer, central air,... View all property information
    Location Information
    Chincoteague Island, Virginia
    5 of 5 stars Reviewed 9 July 2013
    We LOVED this property!!! The pictures did not do it justice. Everything was new, clean, in great condition and perfect. Well stocked kitchen with washer/dryer right off to the...
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    1 / 11
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    3255 Colona Street. Off South Main Street is where you'll find this cute vacation cottage. Peekaboo offers many amenities including a nice eat-in kitchen and screened porch. (1Q/1D/1 BUNK/ 1QSS) You'll enjoy the peek-a-boo view of Chincoteague Bay! (limited waterview) All appliances including... View all property information
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    Chincoteague Island, Virginia
    1 / 14
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    This cottage is peaceful with a great waterfront location on Pine Drive. There is a large yard that overlooks the Assateague Island. The home is nicely furnished, has a large deck area, is pet friendly (dogs only) & offers a small boat dockage. The waterfront is bulk headed which provides a great... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 14
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This cozy ranch styled home overlooks wet lands and is located at 5521 American Circle Drive, Richardson's Landing. Step inside this home and you will find a spacious living room with many windows and a ceiling fan. The living room has a sofa and 3 chairs that surround a TV. The eat in kitchen has... View all property information
    Location Information
    Chincoteague Island, Virginia
    5 of 5 stars Reviewed 12 March 2016
    My family has stayed at this rental for the last few summers when we go to Chincoteague. My favorite thing here is the view of the water from the deck. We love cooking out there...
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    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 located at 7482 Eastside Drive. The upper level of this home has 1 double bed and 4 twin beds. This home features beautiful views that overlooks Assateague Island.... View all property information
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    Chincoteague Island, Virginia
    1 / 15
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    8165 Marsh Point Lane. ** This great rental home will sleep 8 and has an open floor plan, great kitchen with center island, wood floors, master bedroom suite, screened porch, central air conditioning & all appliances. There's also a den and an additional private room on the second level.... View all property information
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    Chincoteague Island, Virginia
    1 / 12
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    ** 7158 Piney Island Road, Unit 1 ** Delightful end-unit townhome overlooking the Assateague Channel and Lighthouse. This unit boasts many fine features including a fully-stocked kitchen, waterside master bedroom suite (with balcony), a fireplace and a 26' flat screen TV with DVD player. Living... View all property information
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    Chincoteague Island, Virginia
    1 / 16
    5 of 5 stars (1) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    ** 4138 Ridge Road ** Light, bright & 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 & more. The home is located just outside of town and offers... View all property information
    Location Information
    Chincoteague Island, Virginia
    5 of 5 stars Reviewed 26 August 2014
    We stayed at Sundance last week and it was great. Very roomy and bright and airy. The king bed in the master bedroom was very comfortable. The kitchen was well stocked and had...
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    Beautiful home in quiet piney island located at 5408 Oak Drive. Enjoy a game room for all ages. Step inside this home and you will be surprised to see a modern interior with white walls and carpeting. The living room is very cozy with a large sectional sofa and 2 chairs. The kitchen has all needed... View all property information
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    Chincoteague Island, Virginia
    1 / 17
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • Shared Outdoor Pool...
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    7665 East Side Drive. Formerly known as "Welcome Aboard" ** NEW FOR 2011 ** Bedding upgrade, 2nd bedroom now has two new twin beds! ** Great 2 bedroom, 2.5 bath townhome in Lighthouse Estates community off East Side Drive. This home features all amenities including central air and washer/dryer.... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 21
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    5386 Main Street. A wonderfully charming Chincoteague home that is fresh, bright and inspirational! The two bedroom/den home features a master bedroom suite with private bath, a second bedroom with twins and a private den off the living room with sleeper sofa. There is another full bath off the... View all property information
    Location Information
    Chincoteague Island, Virginia
    5 of 5 stars Reviewed 4 December 2014
    We were greeted by a Great Blue Heron and a pair of mallards! So peaceful, so quiet! The house was well appointed and met our every need. There was even a list of things to do...
    5 of 5 stars Reviewed 14 October 2014
    We really enjoyed our stay at Sweet Retreat. This was a comfortable and very clean home. They had everything you would ever need. There was plenty of space for the 4 of us that...
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    1 / 14
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    ** 5146 Deep Fern Court, Oyster Bay II ** Nestled on a quiet cul-de-sac in a private community just off North Main Street is where you'll find the charming Cockleshell Cottage. This new 3 bedroom, 3 bathroom boasts a first-floor master bedroom suite, all modern amenities and new furnishings. Relax... View all property information
    Location Information
    Chincoteague Island, Virginia
    5 of 5 stars Reviewed 26 July 2015
    The rental was just perfect! We wished we could have stayed longer. The house was very clean, it was decorated so nice in a nautical theme. We were away from downtown...
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    ** 5321 Cedar Drive ** 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.... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 20
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    6321 Captain's Lane ** 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... View all property information
    Location Information
    Chincoteague Island, Virginia
    5 of 5 stars Reviewed 17 August 2015
    Rental is clean and spacious. Had an absolutely lovely family vacation and no regrets on splurging on this condo! Condo is well equipped with up to date appliances, and staying on...
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    Island vacation rentals - seaside villas, waterfront homes and condos

    Browse through our vacation home rentals, and you’ll discover some very tempting choices for your family vacation. An historic Main Street home is surrounded by a private landscape with a screened porch, bikes and beach toys. A luxurious custom home overlooks beautiful Oyster Bay, and family-friendly condos feature waterside decks, swimming pool and marina.

    Abundant outdoor recreation and attractions

    Naturally, the seashore is the dominant focus for outdoor fun on Chincoteague Island. Fish from the dock or walk the beach. Take a bird-watching hike or bicycle ride through wildlife preserves and quaint island lanes. Enjoy dolphin watching, island tours and spectacular sunset views from your own guided cruise through remote bays and waterways. Either Assateague or Chincoteague beaches are ideal for family picnics and water sports.

    Believe it or not, the wild Chincoteague Ponies are an unusual attraction on adjacent Assateague Island. The kids will love a trip to the Chincoteague Pony Center to enjoy pony rides, a show and riding competition. Book a small, charter deep-sea fishing trip that offers the opportunity to land big game fish from mahi-mahi and tuna to marlin and sharks.

    Leisurely shopping and dining

    As a contrast to all of that outdoor adventure, explore the village feel of the historic downtown and Maddox Boulevard areas. You’ll find exceptional hand-crafted duck decoys and original wildlife and landscape paintings and charming gift shops. To keep you entertained on a lazy sun-filled afternoon, stop in at Sundial Books to browse for book favorites and enjoy a cup of coffee or tea.

    Fresh ocean fare dominates local restaurant menus that are loaded with clams, oysters, and all-you-can-eat seafood platters. Of course, you can’t take the kids on vacation without finding the perfect pizza place, and that would be Famous Pizza Family Restaurant. They’ve been serving home-fresh pizza, cheese steaks and more for over 30 years. And you positively have to stop in at The Sea Shell Café for a gourmet salad and authentic Smith Island Cakes. They even cater to your vacation home, if you want to skip the kitchen duties and enjoy their excellent dinner selections.

    Villa and home rentals – the perfect seashore vacation choice

    There is no better way to enjoy a lazy, leisurely island vacation than from your carefully-chosen home rental. You’ll have plenty of room to relax, waterside views to enjoy and some wonderful home-grilled meals or bountiful breakfasts that will long be memorable for your entire family.