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Holiday Rentals 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 291 Rentals in Chincoteague Island
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    Vacation House1 / 12
    (15)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Epiphany on Deep Hole Creek - Waterfront & Dock - Thanksgiving available!1 / 31
    (44)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Spacious, historic Chincoteague Is. vacation house1 / 13
    (10)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Sea Heart & Soul, Waterfront Memorial Park Rental1 / 32
    (9)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Waterfront
    • Ocean Views
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2017
    We had a wonderful stay and the location couldn't have been better for our family. My husband was able to get up early to fish at the pier and I was able to let the kids sleep...
    Reviewed 10 July 2017
    We had a wonderful time staying at the SHS. The owner was very friendly and acomodating. Our kids loved the playground right across the street! We cant wait to come back!
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    About this property
    SEA HEART&SOUL next to SEA ADVENTURE: This home offers 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, relax and enjoy, coolers, beach chairs, grill, beach toys, storage under...
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    23336, Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tranquil Shores - Relaxation With a Water View1 / 30
    (6)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 1 week ago
    This home was just what we needed for the weekend. It was convenient to get to Main Street for the holiday happenings, stores, and restaurants, as well as convenient to the...
    Reviewed 14 September 2017
    This is a great house in a very good location (though the road is a bit rutted). The view from both decks is spectacular -- beautiful sunrises, even when there are some clouds...
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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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    23336, Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sea Adventure: Waterfront  Views, Pier at this Park Rental!!!1 / 19
    (1)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 7 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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    23336, Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Washer
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Joshua B. Jones Homeplace is a historic waterman's 19th century Victorian home. The home has been newly renovated but still has the beauty and charm of the original home. The home is located on Main Street and is within walking distance of of town to visit restaurants, movie theater and all the...
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    23336, Chincoteague Island, Virginia
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    Waterman's Cottage1 / 21
    (40)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Porch
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 September 2017
    The cottage was cute, but not so clean. The washer overflowed, but the property manager was on it and got a repair person out right away. The kitchen is not stocked well with...
    Reviewed 7 September 2017
    Great island feel. We had an issue with the air conditioning and it was fixed very quickly. Great location with easy walk to wonderful little shops and beautiful water views
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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...
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    23336, Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bayside Sunset, formerly known as Pine Warbler, is a 2 bedroom, 2.5 bath, centrally air conditioned townhome that sleeps up to six (6) people with 1 Queen, 2 Twin, and 1 Queen Sleeper Sofa. Upon entering the home on the first floor you will find a fully equipped kitchen with microwave &...
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    23336, Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    NEW! Canalside 3BR Chincoteague Island Home w/Pier!1 / 26
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Grill
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    What a wonderful house to spend the week. A great place to relax after watching rockets, exploring light houses, and combing the beach. Lots of crabs to come home to. Superb.
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    About this property
    Leave all of your worries behind when you stay at this marvelous 3-bedroom, 2-bathroom Chincoteague Island vacation rental house! Boasting space to sleep 8 guests, water views and a secluded canalside location with private pier, this quaint Virginia property will allow you to leave all your...
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    Location Information
    23336, Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Silver Thatch in Chincoteague1 / 18
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • DVD Player
    • Washer
    • Grill
    • Patio
    • Outdoor Dining Area
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 September 2013
    Really enjoyed ourselves here. It was large enough with enough porches and separate areas to allow everyone space to themselves
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    About this property
    Silver Thatch is a wonderful place to enjoy a Peaceful Island Getaway. Enjoy family gatherings on the spacious deck or curl up with a good book in the screened in living area. Silver Thatch is a beautifully decorated 4 bedroom / 2 bathroom home located close to the Assateague Island National...
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    Location Information
    23336, Chincoteague Island, Virginia
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • DVD Player
    • Wi-Fi
    • Porch
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Melva’s Place is a warm and inviting retreat, located in the Heart of Chincoteague. Upon entering this 1 story home you are greeted by a Fully Stocked Kitchen, Dining Room, Large Living Room with a Queen Sleeper Sofa, 1 Full Bath, and 2 Bedrooms. The first Bedroom is furnished with a Double bed,...
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    23336, Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Outdoor Dining Area
    • Internet Access
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lorna’s Dune is a 2 bedroom, 1 1/2 bath, central air conditioned home that sleeps up to 4 people with 1 Queen and 2 Twin beds. On the first floor you will find the kitchen that is furnished with stove, refrigerator, dishwasher, microwave, coffee pot, crock pot, pots and pans, dishes, glasses,...
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    23336, Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Beautiful Chincoteague Island retreat1 / 15
    (12)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Porch
    • DVD Player
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    • Washer
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 September 2017
    The house was a good location, very close to a lot of stores and attractions. Very cute layout, with a stocked kitchen, screened porch, and a lovely breakfast nook. The beds and...
    Reviewed 22 September 2017
    Enjoyed our stay here. Cozy and close to downtown. All appliances and A/C functioned well (except the vacuum cleaner -- never figured that one out). Screened porch was...
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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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    23336, Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Sidewalk's End1 / 14
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
    • Patio
    • DVD Player
    • Grill
    • Parking
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 July 2014
    This was an incredibly cute place and surprisingly spacious--large living room and master bedroom, comfortable area rugs. I was happy to see a bookshelf with a random...
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    About this property
    Sidewalk’s End is an adorable, 2 bedroom, 1 1/2 bath, central air conditioned cottage located in town for summer evenings spent strolling, shopping, playing miniature golf, exploring the many restaurants, and of course the ice cream parlors. The Comfortable living room with plenty of seating, is...
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    23336, Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Our Sanctuary1 / 22
    (4)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Balcony
    • Terrace
    • Air Conditioning
    • Waterfront
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 July 2017
    This was by far one of the nicer rentals we've ever booked. It had just about everything you need for your vacation. There is a dock area in the back so that you can do some...
    Reviewed 19 August 2015
    This was a wonderful townhouse in a beautiful location. I can highly recommend it and we hope to return next year.
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    About this property
    Our Sanctuary is a Canal Front 2 Bedroom, 2 ½ bath, central air conditioned, town home that sleeps up to six (6) people with 2 Queen ( 1 Queen bed, 1 Queen Sleep Sofa), and 3 Twin Beds. Relax and unwind while enjoying the beautiful water views that the back yard, deck and balcony offer, or spend...
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    23336, Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Duck's Delight - Your Seaside Home Away From Home!1 / 20
    (45)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 days ago
    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
    Reviewed 12 September 2017
    This is a truly well kept house with a great location for a terrific price. I will definitely try to rent it every time we go back to Chincoteague.
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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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    23336, Chincoteague Island, Virginia
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Assateague Overlook #21 / 15
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    • DVD Player
    • Air Conditioning
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 July 2013
    We had a great stay at Assateague Overlook #2. We travelled with our 3 kids (ages 4, 2 and 8 mos) during Pony Swim Week on Chincoteague. The rental was a great location. Not too...
    Reviewed 22 July 2013
    My husband and I came down for our honeymoon--this was our first visit to Chincoteague and we didn't know totally what to expect. I'm glad we chose to stay at this place as it...
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    About this property
    Assateague Overlook #2. is located on the eastside of Chincoteague just off the bank of the Assateague Channel. Enjoy watching the wild ponies from your balcony. Experience the wonderful breezes. Take in the breath taking views of Assateague Island and the historic Lighthouse. You are within a...
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    Location Information
    23336, Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bayberry is an inviting, 2 bedroom, 2 ½ bath, centrally air conditioned, canal front townhome that sleeps up to 6 people with 1 Queen, 1 Queen Sleep Sofa, and 2 Twin beds. This island getaway is the perfect spot for enjoying the Fresh Salt Air from the first floor deck or the second floor balcony...
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    Location Information
    23336, Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Kokomo1 / 14
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Grill
    • Parking
    • Cable/satellite TV
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    • Patio
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Kokomo is a charming, Original Style Chincoteague Cottage, Shabby Chic furnished and decorated, central air conditioned, 2 bedroom, 1 sleeping den with door for privacy, with 2 full baths, that sleeps up to 6 people with 1 Queen, 2 Twin, 1 Twin Trundle, and a Double Futon Sofa. This home boasts a...
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    23336, Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lighthouse Estates #31 / 22
    (2)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Air Conditioning
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 September 2017
    The location was great, watching the lighthouse at night was amazing. The pool was wonderful to have and well cared for.
    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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    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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    23336, Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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    Agape House1 / 15
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Air Conditioning
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 June 2016
    We have been vacationing on Chincoteague for years and Love everything about it, This is a great house with lots of room we had two adults and four teens and it worked out...
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    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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    23336, Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Coco Banana on Chincoteague Island1 / 26
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • DVD Player
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Porch
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 May 2017
    Great location, very well stocked( ie. dish towels, cook ware, seasonings..) This rental is the nicest one I have stayed in and I have been coming to the Island for 20 +years...
    Reviewed 19 August 2016
    My family has declared that Coco Banana is the best 2 bedroom, 2 bathroom rental in Chincoteague! We love the layout of the house, the detail of the décor, the screened porch...
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    About this property
    COCO BANANA is a bright and spacious 2-bedroom, 2-full bath, central air conditioned home, located on a quiet dead-end street near the heart of town. It is just a short walk to historic Main Street where you can explore Chincoteague’s quaint gift shops, restaurants ice cream parlor and movie...
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    Location Information
    23336, Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Delightful end-unit townhome overlooking the Assateague Channel and Lighthouse. This unit boasts many fine features including a fully-stocked kitchen, waterside master bedroom suite (with balcony), and a 28inch flat screen TV with DVD player. Living room has a 32inch flat screen TV with a DVD...
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    Location Information
    23336, Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We invite you to come and explore all that the sea & land offer at Surf & Turf. Upon entering this spacious and comfortable home the first floor greets you with a large family room that is open to the kitchen, separate living room to escape and read a good book, Master Bedroom with king bed and...
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    Location Information
    23336, Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    23336, Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Anchor’s Rest—Centrally located, just a short walk to the carnival grounds, shopping, ice cream, dinner and the movies. This welcoming, spacious rental home features a fully equipped kitchen (don’t forget to bring k-cups!) with abundant counter space opening into the separate dining room. Enjoy the...
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    Location Information
    23336, Chincoteague Island, Virginia
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • DVD Player
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This property has a location that is rich with amenities. Situated right next to Memorial Park, you can sit on the deck and enjoy the water views as the kids run, play, skateboard, fish and crab. The first floor is an open room consisting of the kitchen, dining area and living room (with queen...
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    Location Information
    23336, Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Abbie Thornton Cottage1 / 19
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Air Conditioning
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 August 2015
    My husband and I stayed at Abbie Thornton cottage in August 2015 and are SO happy we booked this place! It was absolutely wonderful, from the screened in porch (perfect spot...
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    About this property
    This charming Chincoteague cottage was built in the 1930's and is located directly across the street from the Chincoteague Bay. Abbie Thornton Cottage has kept much of the original integrity, but has been lovingly restored to offer all the modern comforts of home. There's a cozy screened porch off...
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    Location Information
    23336, Chincoteague Island, Virginia
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This property has a location that is rich with amenities. Situated right next to Memorial Park, you can sit on the deck and enjoy the water views as the kids run, play, skateboard, fish and crab. The first floor is an open room consisting of the kitchen, dining area and living room (with queen...
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    Location Information
    23336, Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cowboy Cottage1 / 18
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 August 2017
    I found Chincoteague Island an enjoyable vacation destination. The Cowboy Cottage is a comforortable, somewhat rustic place to stay. It's central location on the island makes...
    Reviewed 11 September 2016
    We stayed here for a week with our two large dogs and an 18 month old. Loved the open floor plan and the furniture was comfy. Kitchen is well stocked and washer and dryer were...
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    About this property
    Cowboy Cottage is a pet friendly home conveniently located a block from Maddox Blvd., and just a couple of blocks from downtown Main Street. This ranch-style home has an open floor plan and is handicap accessible with a ramp to enter the house and bedroom/bathroom accessibility. There is a large...
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    Location Information
    23336, Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    23336, Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Peter’s House is situated in the Piney Island area. It is within ½ mile of Maddox Blvd., the road to Assateague Island and the beach. It is very convenient to and within walking distance of shops, restaurants, miniature golf and much more. There is off street parking at the house for three...
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    Location Information
    23336, Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, 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
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    • Waterfront
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 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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    Location Information
    23336, Chincoteague Island, Virginia
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    On Island Time1 / 20
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 March 2017
    We have been coming to Chincoteague Island since 1988 and this is the best house we have been to. The décor is sweet and thoughtful. All the little touches are lovely and the...
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    About this property
    Wow... What a show piece! 'On Island Time' is exactly what you expect in your beach home, from the bright and fun decor to the spacious and bright floor plans, all of this wrapped in a traditional Eastern Shore Home. The front enclosed porch is great for reading or just relaxing in the afternoon...
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    Location Information
    23336, Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Bay Daze1 / 17
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Terrace
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 2017
    A beautiful condo with nautical decor, comfortable beds, well-stocked kitchen, large refrigerator and 2.5 baths. Two balconies provide gorgeous views of the waterway, marsh and...
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    About this property
    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 (end unit) offering all the amenities you'll need for a perfect vacation! On the main level you'll find an open...
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    Location Information
    23336, Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Homeport is a comfortable, inviting, 2 bedroom, 1 bathroom, centrally air conditioned home located on a quiet street within a short walk to town. Upon entering the home you are greeted by a large living room with a queen sleeper sofa, and a kitchen that opens onto the back deck and screen porch....
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    Location Information
    23336, Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Paradise by the Lighthouse1 / 8
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 May 2015
    Paradise by the lighthouse is very decieving as from the outside it appears a little worn -but when you step into this good sized split sectioned home you will be amazed at the...
    Reviewed 12 July 2014
    We truly enjoyed our stay. The house was very clean and the decor made us feel right at home! Even the little odds and ends were not forgotten. If you needed something, it was...
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    About this property
    Paradise By The Lighthouse is located on the eastside of Chincoteague just off the bank of Assateague Channel. Enjoy watching the wild ponies from your balcony and experience the wonderful breezes and breathe taking views of Assateague Island and the historic Lighthouse. You are within a stone’s...
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    Location Information
    23336, Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Moorings South1 / 45
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Washer
    • Porch
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    • Waterfront
    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 July 2015
    I just returned from a week in this lovely home with a family group of 7, including my father, who is disabled and can walk short distances with a quad cane but cannot handle...
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    About this property
    The Moorings South is a four bedroom, four bathroom, central air conditioned, luxury style vacation rental that sleeps up to eight people with 2 King/ 1 Queen/2 Twin beds, and is nestled directly on the deep water of the Chincoteague Channel for easy boating. This home has been built on a reverse...
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    Location Information
    23336, Chincoteague Island, Virginia
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Water's Edge1 / 14
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 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
    23336, Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    Las Brisas1 / 16
    (7)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
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    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 August 2017
    We booked this place after our AirBnB reservation was cancelled just 2 months before our vacation. Although we're not picky and were vacationing on a very small budget, we...
    Reviewed 19 July 2017
    Las Brisas is a small, second floor efficiency, on March Island directly off of the bridge entering Chincoteague. We've been going to Chincoteague and have stayed in many...
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    About this property
    Las Brisas is a 1 bedroom, window air conditioned, waterfront condo, located on Marsh Island that sleeps up to 4 people with 1 queen bed, and a full size sleeper sofa. You can enjoy crabbing, fishing, and docking your boat at this private “Island Retreat”. This beautifully decorated, and well...
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    Location Information
    23336, Chincoteague Island, Virginia
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Assateague Light1 / 11
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 August 2012
    Assateague Light is a very nice first-floor waterfront condo facing the Assateague Channel. The view from the deck is spectacular. When we were looking for vacation rentals on...
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    About this property
    This modern 2 bedroom condo located on the first floor features a master bedroom suite with a king bed, private bath and sliding glass door to the waterfront deck. The second bedroom has two twin beds with a full bathroom across the hall. This shared bath offers a walk in shower and washer/dryer....
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    Location Information
    23336, Chincoteague Island, Virginia
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cockleshell Cottage1 / 14
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 26 July 2015
    The rental was just perfect! We wished we could have stayed longer. The house was very clean, it was decorated so nice in a nautical theme. We were away from downtown...
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    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
    23336, Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Captain's Loft1 / 18
    (3)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 September 2017
    Been coming to Chincoteague for years and have stayed all over the island. Hands down this is my favorite place. Clean, plenty of Bedrooms and Bathrooms. It also does have a...
    Reviewed 14 October 2015
    This two-floor unit offered peace and quiet. The quality and amenities were good and more room than we expected. The three bedrooms downstairs included three full baths...
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    About this property
    Captain's Loft has NEW OWNERS! This vacation home is located just a short walk to Maddox Blvd! Close to everything, but situated perfectly for a quiet and relaxing stay. This duplex home features three bedrooms downstairs, and two of those bedrooms have full baths. There's another full bath...
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    Location Information
    23336, Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    • Air Conditioning
    • Waterfront
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beacon View is a beautiful 4 bedroom/ 3 full bathroom home located on the deep water of Assateague Channel. This vacationer’s dream has a gorgeous view of Assateague Island and the Lighthouse and includes a private deep water boat dock for fishing, crabbing or just relaxing and enjoying the...
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    Location Information
    23336, Chincoteague Island, Virginia
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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    Lighthouse Pointe1 / 15
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    One of East Side's most popular rentals! Features include open floor plan with waterside balcony downstairs, and a spacious third level master bedroom suite with private waterside balcony. All levels have balconies or deck! Very conveniently located - close to Memorial Park, restaurants and marina....
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    Location Information
    23336, Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    ***5203 Oak Springs Lane***Very private water front home with acess to the Chincoteague Bay. Private dock for canoes, kayaks and flat bottom boats. Features a lovely pond in the front yard. Large back deck, screen porch, Wi-Fi, private dock & fenced back yard. Nearby is Refuge, A Summer Place and...
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    Location Information
    23336, Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***5215 Shell Drive***'Belle of The Bay' is a unique vacation experience. Premier & private location for total waterfront enjoyment on Chincoteague's Oyster Bay and overlooking Assateague Island. Panoramic views, large multi-level decks & screened porch. 3 bedroom home sleeps 8 and bonus area...
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    Location Information
    23336, Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Joy's House1 / 15
    (1)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 September 2013
    We loved our stay at Joy's House! My husband has been vacationing in Chincoteague since he was a young child and this our second year coming as a family of four. We wanted to...
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    About this property
    Joy’s House is a Charming, 2 bedroom, 2 ½ bath, Chincoteague Style, window air conditioned, water front home with stunning views of the Chincoteague Channel. This home is located close to the Curtis Merritt Harbor for the boating enthusiasts in the family. Breathtaking sunsets, cool salt breezes...
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    Location Information
    23336, Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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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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    Location Information
    23336, Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    Previous
    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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