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Holiday Rentals and Villas in Chincoteague Island, VA

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    Travellers to Chincoteague Island are booking April 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 26 August 2016
    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 / 12
    4 of 5 stars (1) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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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 26 August 2016
    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 / 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 / 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 26 August 2016
    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 / 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 / 27
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Ocean Views
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    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 / 20
    5 of 5 stars (37) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Air Conditioning
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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 / 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 / 18
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    **6378 Cropper Street** There's room for everyone at this grand home! Downstairs you'll find the living room, foyer, formal dining room w/ fireplace, cook's kitchen and great front porch. The second floor features 3 bedrooms, and the third floor is entirely a master bedroom suite with private bath... 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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    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 / 15
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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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
    Location Information
    Chincoteague Island, Virginia
    1 / 20
    5 of 5 stars (1) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Balcony
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    • Waterfront
    • Terrace
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    • x
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    About this property
    Charlotte's Morning Sun - 5321 Sunrise Shore Drive - a brand new waterfront five-star home. (1K,1Q, 1Bunk F/T, 2T, 1Futon) View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 24
    5 of 5 stars (2) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    ** 5173 Winder Lane ** Saltings is a stunning bayfront home with sweeping panoramic views over Chincoteague Bay. The home has an open floor plan with wood floors and beautiful windows. Saltings is nestled at the edge of a salt marsh where indigenous wildlife is abundant and sunsets are mesmerizing.... View all property information
    Location Information
    Chincoteague Island, Virginia
    5 of 5 stars Reviewed 15 July 2016
    We spent a very relaxing week on Chincoteague island at this beautiful house. The neighbours offered to take our boys out crabbing which they greatly enjoyed. We loved the...
    5 of 5 stars Reviewed 21 April 2016
    We stayed for a week at this house in the summer of 2015, and had a wonderful time. The bedrooms were all very comfortable, and we had many at-home dinners enjoying the...
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    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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    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 / 16
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • DVD Player
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    • x
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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
    Location Information
    Chincoteague Island, Virginia
    1 / 29
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Waterfront
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    • ?
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    About this property
    You Will Enjoy Spectacular Sunsets From This Lovely Water home Overlooking The Chincoteague Channel. This home is located at 4635 Main Street. This home is truly stunning from the inside and out. There is great detail on the outside of this house which make it very inviting. The inside of this... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 20
    5 of 5 stars (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • x
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    About this property
    2 story home overlooking tranquil salt marsh located at 4381 Salt Marsh Lane. NEW FOR THE 2010 SEASON A SCREENED IN PORCH. This home has a king bed, a queen bed, and 4 twin beds. Enjoy the many amenities this home offers such as; an open deck, DSL Wireless Internet, private dock, outside shower,... View all property information
    Location Information
    Chincoteague Island, Virginia
    5 of 5 stars Reviewed 25 July 2016
    We stayed here a few weeks ago. We had stayed in another house on the same street in a previous year- have been coming to the island for decades! The AC is COLD, the deck appears...
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    1 / 25
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    This cozy 2 story duplex is perfect for a small family. The large living room has plenty of seating. Enjoy dinner at the dining room table that seats 4. The kitchen has all the needed appliances including a dishwasher. The master bedroom has a king sized bed with 2 chests of drawers for clothing... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 9
    2 of 5 stars (1) Poor
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Porch
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    About this property
    This charming 2 bedroom home features all the amenities you'll need to enjoy a cool, comfortable vacation. Located next door to the Miss Agness house for larger groups, this home is located at 3264 South Main Street. This house comes with a shared pier on Chincoteague Bay. The master bedroom has 1... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 15
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    6321 Captain's Lane ** Villa 203 is a new unit that has been professionally decorated and offers five-star luxury. Spacious and accommodating, the groumet kitchen is perfect for cooking your favorite meals. It's well stocked and ready for your handiwork. There are three bedrooms, including a... View all property information
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    Chincoteague Island, Virginia
    1 / 14
    5 of 5 stars (1) Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Porch
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    5122 Main Street.** Live with history and your own private nature preserve. This updated 19th century island waterman's home is nestled on an acre and a half of secluded land. The Homestead is tastefully furnished and loaded with amenities. Take a shower under the stars or watch the egrets fish in... View all property information
    Location Information
    Chincoteague Island, Virginia
    5 of 5 stars Reviewed 15 August 2016
    We just spent a week at the Homestead, and it was everything we were looking for and more. We had a few semi rainy days and very high temps the whole time there. We all were...
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    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
    Location Information
    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 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    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 / 14
    4 of 5 stars (4) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Porch
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    • ?
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    **3130 Harris Lane** (Off Beebe Road) - Clean, cool and affordable! As one of the newest additions to our vacation rental inventory, Bay Window offers a nice, quiet location and bright, large rooms for your family! Located on a side street not far from South Main Street, you're conveniently located... View all property information
    Location Information
    Chincoteague Island, Virginia
    4 of 5 stars Reviewed 15 August 2016
    We have stayed at the Bay Window several different years and enjoyed staying there. Since we have dogs, it is pet friendly and sits off the Main Street so we can walk our pets...
    5 of 5 stars Reviewed 26 September 2013
    First of all, BAY WINDOW is pet friendly. That was winning point #1 for our angel of a dog. House was clean & showed no evidence of previous dogs. Everything was easily booked...
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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 / 22
    5 of 5 stars (1) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Shared Outdoor Pool...
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    • x
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    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 / 32
    5 of 5 stars (2) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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    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 / 11
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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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 / 17
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    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 / 17
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Internet Access
    • Terrace
    • Satellite TV
    • Balcony
    • Waterfront
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
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    • Smoking allowed
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    About this property
    ** 6151 Marsh Island Drive, Marsh Island // Waterfront // Beds: 2K, Trundle (2T) ** (Formerly known as Bacon's Point) Escape from the hustle and bustle of everyday life at this little slice of paradise nestled on the edge of the Chincoteague Bay! Bay Daze is a clean, comfortable and modern townhome... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 21
    4.5 of 5 stars (3) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Grill
    • DVD Player
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
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    About this property
    7556 East Side Drive - -Located on the Assateague Channel, this is your chance to watch the ponies from your own deck. A wonderful panoramic view awaits you…to the left is the Assateague Bridge; right of the bridge is the Assateague Lighthouse and ponies; and to the far right is Tom’s Cove and the... View all property information
    Location Information
    Chincoteague Island, Virginia
    5 of 5 stars Reviewed 21 May 2016
    We stayed at Dockside as our family vacation. The house was great, it had everything that you could ever want or need. The kitchen had everything including wine glasses. The...
    5 of 5 stars Reviewed 3 January 2016
    We had a lovely stay! The house is well laid out,, clean and has a wonderful water view from the living room and its own dock just a few steps off the back deck. We arrived in the...
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    1 / 23
    4 of 5 stars (5) Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Shared Outdoor Pool...
    • DVD Player
    • Internet Access
    • Porch
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
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    About this property
    3867 Main Street.** Huge 5 bedroom, 2.5 bath Victorian home right on Main Street - close to downtown. Pet friendly & big enough to accomodate 12! Beautiful balcony views of the island & Chincoteague Bay. Fantastic wrap-around screened porch out front! Great White includes access to a swimming... View all property information
    Location Information
    Chincoteague Island, Virginia
    5 of 5 stars Reviewed 29 March 2015
    We loved this rental property. Lots of room and places to hang out with friends and family. The deck was great in the evenings for a glass of wine :) Our kids really enjoyed...
    4 of 5 stars Reviewed 12 March 2015
    I have stayed in this house may times with my family and have had a wonderful time. Is spacious and have all the commodities needed for our group (we were nine). Very quiet and...
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    1 / 44
    5 of 5 stars (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Balcony
    • Terrace
    • Internet Access
    • Grill
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
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    About this property
    ** 5118 Richardson Street, Richardson's Landing ** 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... View all property information
    Location Information
    Chincoteague Island, Virginia
    5 of 5 stars Reviewed 2 weeks ago
    Absolutely loved paradise view from Chincoteague Resort Vacations. The scheduling was a breeze and everything was from scheduling to rental agreements to check in were a breeze...
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    1 / 21
    2.5 of 5 stars (4) Poor
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Grill
    • Porch
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
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    About this property
    3464 Ridge Road.** Luxury water view vacation rental home with dock access. Newly constructed, 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.... View all property information
    Location Information
    Chincoteague Island, Virginia
    3 of 5 stars Reviewed 4 January 2016
    I thought the house was a good size but it could use a DEEP cleaning and some updated furniture and more TV's. The deck was unusable and dirty and the house probably was sealed...
    3 of 5 stars Reviewed 27 September 2015
    There are some things to love about this rental. First, it is spacious and relatively updated. However, there are plenty of issues at the detail level that we didn't find...
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    1 / 16
    4 of 5 stars (2) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Shared Outdoor Pool...
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
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    About this property
    6321 Captain's Lane ** 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... View all property information
    Location Information
    Chincoteague Island, Virginia
    5 of 5 stars Reviewed 3 August 2014
    This was a wonderful place to stay. The pictures don't do this place justice. Definitely will stay again.
    3 of 5 stars Reviewed 26 August 2013
    third floor rental with view of marina and bay...good living room couches....nice mbr furniture (if thats important)...but, I found it a struggle to find basic utensils in the...
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    1 / 15
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
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    About this property
    Luxurious 2 bedroom, 2 bath waterfront townhome with views you won't believe! This home is located at 7622 East Side Drive. It is tastefully decorated with work of local artisans. All amenities are provided. The master bedroom suite has a king bed and a waterside balcony! The second bedroom has 1... View all property information
    Location Information
    Chincoteague Island, Virginia
    5 of 5 stars Reviewed 8 July 2012
    I recently stayed at the stingray with my husband, our two-year-old son, and my mother who came for a few nights. The condo was well outfitted, comfortable and clean. It was...
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    1 / 15
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Internet Access
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
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    About this property
    ** 7718 East Side road ** 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... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 13
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • DVD Player
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
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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 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
    Location Information
    Chincoteague Island, Virginia
    1 / 18
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Grill
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
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    About this property
    ** 3749 Willow Street ** Looking for a relaxing beach vacation? Look no further! Enjoy a relaxing stay in this beautifully decorated island cottage. A quiet location to get the much needed R&R not to mention the extras such as bikes, wifi and a Nintendo Wii! BEDS: Q/B(2T) Additional amenities... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Balcony
    • DVD Player
    • Grill
    • Internet Access
    • Terrace
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • ?
    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
    Location Information
    Chincoteague Island, Virginia
    1 / 15
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Shared Outdoor Pool...
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • ?
    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 / 22
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Grill
    • DVD Player
    • Waterfront
    • Internet Access
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
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    About this property
    5543 Hibiscus Dr.** Beautiful custom waterfront home in Oyster Bay. The open floor plan is bright and airy with plenty of room to move around. The downstairs features an open living & dining room w/ gas fireplace, kitchen, and a bedroom and bathroom. Upstairs you'll find the other 2 bedrooms and... 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
    • Shared Outdoor Pool...
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • ?
    About this property
    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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    1 / 12
    1 of 5 stars (1) Terrible
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • ?
    About this property
    7482 East Side Drive. ** This great 1BR waterfront condo overlooks Assateague Island and lighthouse. Your rental includes use of a private deep water boat slip all week. So bring your boat and leave it in the water! Nicely furnished,( 1Q/ 2T) this unit has a great location - there's a marina &... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 8
    4 of 5 stars (1) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Shared Outdoor Pool...
    • DVD Player
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
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    About this property
    6321 Captain's Lane ** A SENSE OF THE TROPICS! This British Colonial style villa is one of our most popular villas. You can enjoy romantic sunsets on the waterside balcony at the end of the day, or enjoy a soothing soak in a luxury jetted tub located in the master bath. The master bedroom suite... View all property information
    Location Information
    Chincoteague Island, Virginia
    4 of 5 stars Reviewed 15 September 2015
    This unit is easily accessible, and nicely decorated. It truly felt like home for a week. Its a short walk to restaurants, shops, and groceries in downtown. Sit on the deck and...
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    1 / 25
    3.5 of 5 stars (3) Average
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Air Conditioning
    • DVD Player
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
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    About this property
    4662 Main Street. ** A beautiful Chincoteague home - new on the vacation rental market. Chincoteague Charm is a beautiful 3BR Chincoteague home located on North Main Street.( 3Q/ 4T/ 1QSS). It's just across the street from Chincoteague Bay and there is water access to the bay for kayaks & canoes.... View all property information
    Location Information
    Chincoteague Island, Virginia
    5 of 5 stars Reviewed 10 August 2015
    This was a wonderful beach house for our extended family vacation. Our four sons, their significant others and our two grandsons were able to sleep comfortably, eat meals all...
    3 of 5 stars Reviewed 8 July 2015
    We rented Chincoteague Charm and its guest cottage from June 28th- July 5th 2015. We have been traveling to the Island for the last 6 years during this time frame and it is a...
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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.