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Holiday Homes 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 276 Rentals in Chincoteague Island
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    Jay's Retreat-Kayaker’s Delight use of 2 Kayaks; Oct/Nov Specials Start at $591 / 22
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Sea Heart & Soul, Waterfront Memorial Park Rental1 / 32
    (11)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Vacation House1 / 12
    (20)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Spacious, historic Chincoteague Is. vacation house1 / 13
    (12)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 August 2018
    The home was cozy, spacious and well equipped with anything we might need for the week-including a stroller, pack-n-play, beach toys, books, games, Barbie dolls and movies. In...
    Reviewed 12 June 2018
    This place was amazing. Spacious well kept house. Our own private drive. Close enough to stuff so we could get there quickly but not right in the middle of it all. We loved the...
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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...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sea Adventure: Waterfront  Views, Pier at this Park Rental!!!1 / 19
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Ocean Views
    • DVD Player
    • Washer
    • Air Conditioning
    • Waterfront
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 August 2018
    This was a lovely three bedroom house that was just perfect for us and our two young kids. With or without kids the location is very good, close to Main Street and a quick ride...
    Reviewed 8 July 2016
    We had rented both houses SHS and SA for our family/friends with kids. The house was very clean and comfortable for all. Very kid friendly, since it was just across from the...
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    About this property
    SEA ADVENTURE next to Sea Heart and Soul are 2 miles from Assateague Island and 5 miles from beach front fun. Check-in 4pm/ check-out 12pm. $229.00 per night. This home, right out your front door, has the coolest waterfront park ever!!! Chincoteague Veteran's Memorial Park, for the recreation of...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Waterfront, 5 BR, 4 BA, Elevator, sleeps 101 / 48
    (1)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Patio
    • Grill
    • Washer
    • Waterfront
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 June 2017
    Our family loved this home. It was spacious, comfortable, well appointed and oh that view. I ( the family chef) was very pleased with the state-of-the-art kitchen...I didn't...
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    About this property
    The Moorings North is an unique architecturally designed luxury 5 bedroom home in the heart of Chincoteague Island. The house is elegantly decorated and has mesmerizing panoramic views of Chincoteague Bay. It is conveniently located in walking distance to small shops, a coffee house, and...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Beautiful Chincoteague Island retreat1 / 15
    (18)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Porch
    • DVD Player
    • Parking
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Cute little neighborhood off Main Street. It's an easy walk to the shops and restaurants downtown. Of course, the main attraction for us is always the beach at Assateague. We...
    Reviewed 5 September 2018
    Nice location walking distance to town and to the pier for fishing. Located on a quiet street. House was cozy and decorated nicely.
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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...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Cozy cottage near Old town Fishing Village1 / 12
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Private Garden
    • Washer
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 August 2016
    Good:- Clean, comfortable and functional- Location walkable to Main St shops and a bowling alley- Window air conditioners worked wellCould be improved:- Owner's...
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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...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Tranquil Shores - Relaxation With a Water View1 / 30
    (11)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Grill
    • Waterfront
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 July 2018
    Wow! Exceptionally close (walking distance) to both Assateague National Wildlife Refuge AND family friendly activities, such as bike shops and eateries. Very quiet...
    Reviewed 19 July 2018
    Communication with the owner was great. The house was in a convenient location near downtown on a very quiet street. The kids were able to ride their bikes there safely. We...
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    About this property
    Peaceful 3 bedroom/2 bathroom home located directly on Eel Creek. Appreciate the natural beauty of Chincoteague Island with gorgeous nature views from both the lower level screened in porch as well as the balcony off of the master suite. Enjoy relaxing mornings with the sunrise and breeze filled...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sunset Bay Villas Chincoteague Island - Sunset in Paradise1 / 24
    (8)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 July 2018
    This property was perfect for our family (family of 4 plus 2 grandparents). Annie was a pleasure to work with right from the beginning. Payment schedule was reasonable and...
    Reviewed 27 February 2018
    We stayed in Sunset in Paradise for a week a few years ago and absolutely loved it (and rented again for summer 2018)! The owners are very responsive, hospitable, and helpful in...
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    About this property
    ANOTHER DAY IN PARADISE CHINCOTEAGUE BEAUTIFUL BAY FRONT CONDO WITH AMAZING WATER VIEWS Owner operated by: Annie Switzer Call 240/498/0074 *** Booking Fall 2018 *** PLEASE CONTACT OWNER BEFORE BOOKING SUMMER 2019 Unit 213 - 'Sunset in Paradise' at Sunset Bay Villas *** Please see FKN 7097918...
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    Location Information
    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Duck's Delight - Your Seaside Home Away From Home!1 / 19
    (46)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Grill
    • DVD Player
    • Wi-Fi
    • Patio
    • Parking
    • Porch
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 May 2018
    This house is a 5 star! Great location people! Very neat, clean and cozy. Beds are comfortable, kitchen has everything you need to cook and a screen porch to relax. Price is...
    Reviewed 13 December 2017
    We had a wonderful time at duck's delight. The house was great and the ducks even came to visit one morning. It was awesome!!! Thanks so much,The Frey's
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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...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Patio
    • Private Garden
    • Wi-Fi
    • DVD Player
    • Grill
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Check out our October & November Specials. Rates as low as $69/Night plus tax and fees. ****************************Now renting for 2019*********************************** Pets Considered: $100/wk. for first pet; $50/wk. for second. Prorated...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sunset Bay Villas - Another Day in Paradise1 / 33
    (10)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Washer
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 2018
    The location of this condo is amazing. You have gorgeous views of the bay from the living room - dinning room area and the master bedroom. The sunsets were amazing. We liked...
    Reviewed 3 April 2018
    Annie was so helpful & always prompt with answering any questions I had. The condo was very clean, spacious & suited our needs perfectly! The location is awesome being...
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    About this property
    ANOTHER DAY IN PARADISE CHINCOTEAGUE BEAUTIFUL BAY FRONT CONDO WITH AMAZING WATER VIEWS Owner operated by: Annie Switzer Call 240/498/0074 *** Booking Fall 2018 & Beyond *** PLEASE CONTACT ME BEFORE BOOKING SUMMER 2019 Unit 103 - 'Another Day in Paradise' Unit 213 - 'Sunset in Paradise' 2nd...
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    Location Information
    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Key West Cottages1 / 4
    (10)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Patio
    • Balcony
    • Hot Tub
    • Air Conditioning
    • Parking
    • Shared Indoor Pool
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 September 2018
    Was a beautiful place to stay. Made for two. Bed was comfortable. Living room couch should be one that reclines back. Was uncomfortable sittingStraight and looking at a tv...
    Reviewed 5 August 2018
    Key West Cottages Chincoteague was the perfect little getaway. The cottage was clean. The grounds were well kept.. Expect we will rent here again.
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    About this property
    Beautiful cottages located in the heart of Downtown Chincoteague with views of the Chincoteague Channel and Bay. The Key West Cottages are equipped with full kitchens, cozy living rooms, Queen bedrooms and large tiled showers. Amenities such as an indoor pool, hot tub and outdoor pool next door...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Air Conditioning
    • Housekeeping Included
    • DVD Player
    • Washer
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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,...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Dancing Water View1 / 9
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 2018
    This place is spectacular- already discussing another visit! Thank you!! Very clean, dock was great, nice breeze nightly. Central to everything.
    Reviewed 9 April 2018
    Beautiful views of Asseteague Island with lighthouse, ponies (with binoculars), fun dock to crab, kayak, or keep boat. Furniture and beds very comfortable and kitchen with...
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    About this property
    New Chincoteague rental with panoramic views of Asseteague Island, ponies and lighthouse. Enjoy sunsets, crab, fish, swim, and kayak from shared dock with optional boat slip. 2 bedrooms (full and 2 twin bunks) (queen) pullout queen couch in living room. One full bathroom. Newly renovated with new...
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    Location Information
    Chincoteague Island, Virginia 23336
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    A Getaway1 / 20
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 June 2018
    We recently stayed at A Getaway this year. It was perfect for the two of us (retired couple). The house was spacious and very clean. Housekeeping staff had done a great job! We...
    Reviewed 20 May 2018
    This house is located just off the Main road about a mile from town in a quiet community. Very clean with everything one might need. Well furnished and decorated it is an ideal...
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    About this property
    A Getaway is a bright and cozy home nestled between pink Crape Myrtles in the private, secluded neighborhood of Oyster Bay II right off of North Main Street. This home features a 12 x 24 screened in deck that is perfect for outdoor gatherings, dinners, and making memories. With clean, functional...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lighthouse Estates #31 / 22
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 September 2017
    The location was great, watching the lighthouse at night was amazing. The pool was wonderful to have and well cared for.
    Reviewed 29 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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    About this property
    This comfortable, family friendly vacation rental is waiting for you to enjoy. This unit has pool access and dock access directly across the street for easy access for those fun family fishing and crabbing experiences. It is just a short distance to Memorial Park and Etta's Waterfront dining. The...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cockleshell Cottage1 / 14
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Air Conditioning
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 June 2018
    This home by far was the best rental we have had yet. From the quiet peaceful area to the wildlife seen just from the backyard. Close enough to enjoy walking to the shops or...
    Reviewed 24 May 2017
    This home was decorated beautifully and was more than roomy for the two of us plus our 2 yorkies. Loved sitting on the back screened in porch while reading or eating ice cream...
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    About this property
    Nestled on a quiet cul-de-sac in a private community just off North Main Street (Oyster Bay II) is where you'll find the charming Cockleshell Cottage. This new 3 bedroom, 3 bathroom home boasts a first-floor master bedroom suite, all modern amenities and new furnishings. It is handlcap accessible....
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Cedar Cove1 / 25
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Wi-Fi
    • Waterfront
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 July 2018
    Cedar Cove was a great place to stay. It was fully equipped with everything we needed and was right along Oyster Bay. It was also very close to everything. Would definitely stay...
    Reviewed 17 September 2017
    Great home for our large family. Quiet location within a bike ride of everything Chincoteague has to offer. Would definitely book again.
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    About this property
    Beautiful custom waterfront home in Oyster Bay. The open floor plan is bright and airy with plenty of room for everyone. The downstairs features an open living & dining room w/ gas fireplace, kitchen, and the master bedroom and bathroom. Upstairs you'll find the other 2 bedrooms and bathroom, as...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Lavinder House1 / 36
    (1)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 November 2017
    This gerrymandered Victorian is the almost perfect weekend get-a-way rental - except . . . Of the five bedrooms, there is only one that you can get to without climbing steep and...
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    About this property
    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, Lavinder House tells its...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Windrush1 / 25
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 May 2018
    Looking for a secluded gem to get away for a few days? We were and this place fit the bill to a T! From the huge wrap-around deck, to the comfortable beds, the Windrush was the...
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    About this property
    Our guests come year after year to relax and enjoy truly fabulous views of our famous Chincoteague Bay sunset! This roomy, attractively decorated home is surrounded by water views, wetlands and birds! Windrush boasts lots of outdoor space including two screened porches, open decks/balcony's and a...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Grill
    • Terrace
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***4473 Deep Hole Road*** This wonderful duplex has all the amenities you'd want including LOCATION!! Just off Maddox Blvd., you have easy access and can walk to everything! ***Electric Grill*** Bed Sizes: 1 Queen, 1 Twin Daybed w/Trundle, 1 Queen Sleep Sofa*** Prime Season Rates: $795...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Epiphany on Deep Hole Creek - Waterfront & Dock -wow!1 / 31
    (44)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Ocean Views
    • Patio
    • DVD Player
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 June 2016
    My family and I thoroughly enjoyed our stay at the Epiphany house recently. The house is fully equipped with EVERYTHING you'll need to make your stay wonderful. We packed so...
    Reviewed 1 September 2015
    And what a week it was. The teens made the most of the clear, sunny days by swinging in the hammock, riding bikes, and kayaking and crabbing (for the first time). The parents...
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    About this property
    Epiphany on Deep Hole Creek. Deep Hole Creek Vacation Rentals Member, Chincoteague Chamber of Commerce Pets subject to approval and an additional fee. See DeepHoleCreek s ite for more info and photos.! Scroll down to email Blair & Martha (owners) . Or Call Blair & Martha at the number listed for...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
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    Catch of the Day is very comfortable and affordable duplex home that will cater to all of your vacation needs. This can be your home away from home - near the beach! The first level offers a large living room, a bedroom (D), an eat-in kitchen, 1/2 bath and very nice screened porch. There are two...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Red Cedar1 / 16
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • DVD Player
    • Wi-Fi
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 June 2017
    Comfortable 3 bedroom house surrounded by nature. At various points we saw herds of goats, llama, or ponies, raccoons, opossum, a variety of birds, and at night the chatter of...
    Reviewed 30 September 2016
    My wife and I stayed here in early September, 2016 for four nights to go kayaking and explore the area. The house worked very well for us. The beauty of the Red Cedar is the...
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    About this property
    Nature calls at this nicely appointed 3 bedroom rental home! Red Cedar is nestled on the edge of a huge expanse of nature preserve-type land where you'll see all types of native wildlife. Birders bring your life list. The home features modern amenities, offers a first floor bedroom, full laundry,...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    As one of our newest vacation rental listings, we're pleased to be able to offer you 'A Sunshine Cottage'! With all the charm of a Chincoteague-style cottage, you'll be reminded of the days gone by. The front porch is the perfect spot to relax with a cool drink and book, and the convenient in-town...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Nestled beneath the tall pines is where you'll find this delightful Piney Island home. The Bird House features an open living room/kitchen/dining area, and extra 'family' space in the private den. The many large windows throughout the home create a bright, airy atmosphere. Enjoy relaxing breezes on...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Daisey Cottage1 / 15
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Reviewed 22 July 2018
    This cottage was adorable and had everything we needed. It made our beach vacation absolutely wonderful! The layout was open and the decor was adorable. The master bedroom...
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    About this property
    Quaint and charming island cottage with all the amenities! Located on the southern end of the island, Daisey Cottage offers everything you'll need for an enjoyable vacation - central a/c, dishwasher, WiFi, washer/dryer and more. And it's even pet friendly! Additional amenities include: 4 pets max....
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Grey Heron is an amazing contemporary waterfront home nestled on the shoreline of Chincoteague Bay. You'll love the floor plan; a terrific great room with wood floors flanked by a kitchen on one side and a fireplace on the other. And great windows throughout! There's also a 'sitting room' with...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sunset Bay Villa 2031 / 52
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed 28 September 2016
    My family and I were extremely satisfied with our stay at Sunset Bay Villa 203. The unit is tastefully decorated without being beach tacky.. The furniture is relatively new...
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    About this property
    Villa 203 is a new unit that has been professionally decorated and offers five-star luxury. Spacious and accommodating, the gourmet kitchen is perfect for cooking your favorite meals. It's well stocked and ready for your handiwork. There are three bedrooms, including a master bedroom suite with...
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    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tall Pines1 / 10
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Reviewed 21 June 2017
    We stayed at Tall Pines on the advise of a friend. She said it was small, but nice.The house is all we needed as a family of four. The queen bedroom was bright and airy. The...
    Reviewed 29 August 2015
    Pros: Nestled in pine forest, well shaded so that AC was not necessary for most of our 2 week stay (esp when we could borrow fans from the management company). Very quiet...
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    About this property
    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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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Water's Edge1 / 34
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
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    Reviewed 25 May 2017
    Water's Edge is in a great location - right on the water and close enough to walk into town. The house was clean and equipped with anything you might need. As mentioned in...
    Reviewed 18 October 2016
    This recently renovated home features an open floor plan with wrap around windows facing out to the water. The small watch tower at the top of the house has stunning views and...
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    About this property
    Water's Edge is an adorable Bay Front cottage in walking distance to Chincoteague's Historic Downtown. You'll be impressed by the charm of this home from the time you pull in the driveway. On the first floor you'll find a full bathroom with an open great room with expansive bay views. There is a...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Come enjoy this 2-bedroom, 2.5 bath townhouse in the Lighthouse Estates community off East Side Drive. There is a community pool as well as water access and a dock (shared) to fish and crab from. This unit features a washer/dryer, wireless internet, central air conditioning and all the other...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    About this property
    As a classic Chincoteague-style home, Hopkin's House is situated on the East Side of Chincoteague Island and overlooks the Assateague Channel. You'll enjoy a wonderful, relaxing vacation at this 3 bedroom home; it's just a short distance from the public boat ramp, Memorial Park, a restaurant and...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Bay Dreamer is a spacious 3 bedroom duplex home with multiple porches and decks and spectacular sunset views, just minutes from downtown. When you enter the home you'll find a furnished rec room. The second floor features an open living room (queen sleeper sofa), dining area and kitchen. There is a...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    About this property
    Aptly named, you'll enjoy a nice relaxing vacation at 'Tranquil Escape!' As one of the newest additions to the vacation rental market, this home is located in a quiet residential neighborhood and features expansive porches and outdoor areas for you to enjoy! With 4 bedrooms, 3.5 bathrooms, an...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    ***5505 Warren Street*** Lovely spacious3 BR canal home at Northern end of island is top notch for a delightful vacation experience. Wildlife and birdwatching throughout the day with panaramic views throughtout. Open floor plan with large dining area and back screened in waterfront porch....
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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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    ***6402 Teal Lane*** The unobstructed view of Eel Creek and Little Oyster Bay will get your attention at sunrise and sunset! Put your kayak in the water at the shared dock at high tide. Now has WiFi and 42' TV*** This Property accepts Weekly Rentals Only.*** Bed Sizes: 2 Queen, 1 Bunk Bed...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sunset Bay Villa 2211 / 19
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Reviewed 20 July 2015
    Excellent and clean unit in a nice condo site. Close to the main area of town. Large unit with all the comforts of home. All household items we needed were there and in good...
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    About this property
    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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    Location Information
    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Misty's Thicket1 / 16
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Reviewed 28 September 2017
    Our family's second visit to Misty's Thicket was just as perfect as our first. Very comfortable house and the dock for crabbing is where we spend most of our time. We caught...
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    About this property
    Located on South Ridge Road, this lovely town-home features a private pier, central air conditioning, and galley style kitchen complete with a dining area and all necessary appliances. The cozy living room leads you onto one of two screened in porches perfect for unwinding with family and friends....
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Agape House1 / 15
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Reviewed 4 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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    About this property
    A great three bedroom home with a convenient in town location - just a short distance to Maddox Blvd. and Main St. for dining, shopping, etc. The master suite has a queen bed and private bathroom with TV. The second bedroom offers two queen beds and lots of extra space. Through the open dining and...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Hill House1 / 18
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Reviewed 14 September 2013
    My family of five stayed with our in-laws with their family of six at this beautiful home in July of this year. Right on Main Street, within walking distance of a terrific...
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    About this property
    Welcome to the 'NEW' Hill House! Wonderful traditional island home with fantastic new upgrades! The kitchen has recently been renovated, along with the bathrooms. Excellent in town location, walk to dinner, movie, shopping & galleries. Hill House features 4 bedrooms and 2.5 bathrooms, with a first...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    Bay's Landing1 / 10
    (1)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Reviewed 25 May 2018
    We've stayed on Marsh island several times but this was the first time at Bays landing. The view is amazing and having a garage was great. But the there is no wifi so we had to...
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    About this property
    ***6153 Marsh Island Drive-Marsh Island*** The owners of this new vacation rental have taken special care to provide their guests with many extras, including 1 person kayaks, beach items and a crab pot for your use. The view looking across Chincoteague Channel to Reed Memorial Park is...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Charlotte's Morning Sun1 / 26
    (2)Average
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    Set in the boutique residential community of Oyster Bay II, ‘Charlotte's Morning Sun’ is a stunning 5-star waterfront home that offers unobstructed water views and breathtaking vistas of Oyster Bay. Flowing generously over two levels, Charlotte features 4.5 bathrooms and 4 light-filled bedrooms,...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    ***4379 Ridge Road*** Lovely 2 bedroom home conveniently located on Ridge Road, not far from Maddox Blvd, with many great island attractions. Perfect house for a family of 4! This house offers extra space in the large sunroom. Bright and airy, the sunroom works for both cool and warm weather. The...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Sea Tag #221 / 19
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Reviewed 13 August 2015
    Nicely remodeled 2 BR/1 BA Condo. Great view of Assateague Island & the lighthouse. Perfect for pony penning & bring your binocs to view the ponies year round. Rental...
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    About this property
    We are pleased to be able to offer you this fabulous 2nd level unit! The interior has been completely renovated, from the drywall and paint, to the furniture! You'll enjoy all modern amenities including flat-screen TVs (3), internet, washer/dryer facility and updated kitchen (appliances, cabinets,...
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    Location Information
    Chincoteague Island, Virginia 23336
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Enjoy some of the island's best water views overlooking Oyster Bay from nearly every room of this custom beach home! Located on a bulk-headed waterfront lot in Richardson's Landing, you can fish and crab from the backyard! A wonderful feature of this spacious home is that you'll find your bedrooms...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    ****6300 Church Street **** Affordable vacation rental in historic downtown Chincoteague. Walk to shops, restaurants, fishing pier, waterfront park and farmers market. First floor bedroom, both bathrooms downstairs. Enjoy the back screened porch after the beach or relax in the front porch swing....
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Paradise View1 / 44
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Reviewed 14 September 2016
    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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    About this property
    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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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    1
    Island holiday rentals - seaside villas, waterfront homes and condos

    Browse through our holiday home rentals, and you’ll discover some very tempting choices for your family holiday. 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 holiday 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 holiday home, if you want to skip the kitchen duties and enjoy their excellent dinner selections.

    Villa and home rentals – the perfect seashore holiday choice

    There is no better way to enjoy a lazy, leisurely island holiday 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.

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