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    Travellers to Chincoteague Island are booking April dates now. Secure your holiday rental today, and have the perfect trip.
    All 299 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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    Sea Heart & Soul, Waterfront Memorial Park Rental1 / 32
    (9)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 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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    Waterman's Cottage1 / 21
    (40)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Secure Parking
    • Porch
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 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 6 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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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 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
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    • Internet Access
    • Air Conditioning
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 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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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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
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    • 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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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, 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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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Duck's Delight - Your Seaside Home Away From Home!1 / 20
    (44)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Grill
    • DVD Player
    • Wi-Fi
    • Patio
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    • Porch
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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.
    Reviewed 11 April 2017
    Staying here during spring break has become a tradition in our family! We love everything about this place! The location is great, the amenities were great and we enjoyed...
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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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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • DVD Player
    • Wi-Fi
    • Porch
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    • 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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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, 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 13 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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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    • Ocean Views
    • Patio
    • DVD Player
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 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 31 August 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 Fall dates available, Including Thansgiving! Pets subject to approval and an additional fee. See Deep Hole Creek s ite for more info and photos.! Scroll down to email Blair & Martha (owners) ....
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Key West Cottages1 / 4
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
    • Patio
    • Central Heating
    • Terrace
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 October 2017
    This was an adorable little cottage with some fantastic amenities. The bed was really comfortable and the rain shower was nice. A full kitchen with coffee maker, dishes...
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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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    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 13 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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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Porch
    • Parking
    • Washer
    • DVD Player
    • Air Conditioning
    • Grill
    • Waterfront
    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
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Cozy cottage near Old town Fishing Village1 / 12
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Private Garden
    • Washer
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    • 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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Air Conditioning
    • Housekeeping Included
    • Ocean Views
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Waterfront
    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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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Patio
    • Housekeeping Included
    • Grill
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy what nature has to offer in this quiet but active resort island on Virginia's Eastern Shore. The atmosphere is a relaxed one yet there is an extensive amount of activities for vacationers. From surf, bay or offshore fishing to kayaking, sunbathing, bird watching, hiking and biking nature...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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
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    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
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    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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    Location Information
    Chincoteague Island, Virginia 23336
    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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    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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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 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 10 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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    Location Information
    Chincoteague Island, Virginia 23336
    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
    Chincoteague Island, Virginia 23336
    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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    • 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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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Sunny Shack1 / 14
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Balcony
    • Terrace
    • Internet Access
    • DVD Player
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 September 2016
    One thing to note, the dock pictured is across the street -- not a terribly busy street -- but still not on property "proper." Our kids loved crabbing and catching...
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    About this property
    Words cannot describe this top-of-the-line luxury townhome. The moment you walk in, you'll find a game room with pool table board games and a large flat screen TV. The second level is a spacious open floor plan with views of the water from just about everywhere. The chef's grade kitchen has...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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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
    • Grill
    • Porch
    • Cable/satellite TV
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    • Air Conditioning
    • Washer
    • 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
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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
    • DVD Player
    • Washer
    • Waterfront
    • Air Conditioning
    Suitability
    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 17 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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    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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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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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
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Whispering Pines1 / 24
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Cable/satellite TV
    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 August 2017
    Great location...close to harbor for flounder fishing! Enjoyed the bikes at the house. We visit Chincoteague on a regular basis. Just love the island!
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    About this property
    Whispering Pines is a clean and comfortable duplex home located at the south end of the island next to the old Beebe Ranch of Misty fame. The property was once part of the Beebe Ranch so Misty probably grazed there! Whispering Pines accommodates up to 8 guests, utilizing the sleep sofa in the...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Pier Pressure1 / 16
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • DVD Player
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    WATCH SPECTACULAR SUNSETS FROM THIS LUXURY TOWNHOME! This exceptionally beautiful 3 bedroom/2 bath luxury vacation rental home has central AC/heat and will accommodate 6 guests. Amenities include a designer kitchen, Jacuzzi tub & top of the line upgrades throughout the home. The master bedroom and...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    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
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 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 15 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 13 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
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Tall Pines1 / 8
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    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, 2 Bathrooms, Sleeps 6
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    ' TEAGUERS DELIGHT ' Upscale Island Home with HOT1 / 16
    (4)Excellent
    2 Bedrooms, 4 Bathrooms, Sleeps 15 Quick View
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    • Grill
    • Parking
    • Cable/satellite TV
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    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 July 2016
    This was our 2nd year . this house is perfect for a large family vacation tim and Collen keep this clean and have a well stock kitchen every thing you need is there house is...
    Reviewed 31 August 2015
    We have been visiting Chincoteague for over 40 years. We have rented many houses on the island but this home is truly a home away from home. This was our first time using VRBO...
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    About this property
    Fresh redo on this spacious and comfortable home, new carpet, flooring, furnishings, mattresses, granite counter tops, tile work and more ! This house has extensive accomadations, two and a half bathrooms and an outdoor shower and foot washing station make as well as a private outdoor hot tub...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 15
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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
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    • 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 18 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
    Chincoteague Island, Virginia 23336
    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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    About this property
    What a beautiful home! This classic downtown Victorian is perfect for your vacation. The spacious first floor offers a large living room, formal dining room, fully equipped kitchen screened porch and queen bedroom plus half bath. Upstairs you'll be welcomed by two large bedrooms one Master Suite...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Carriage House1 / 16
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    About this property
    Rest and relax at the charming Carriage House while enjoying all of the modern conveniences of home. Built in a quiet community (Oyster Bay II), this home features a large and spacious kitchen, with an open concept living room and dining room. Plenty of sleeping space with a 1st floor master...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    ***5348 Oak Drive-Piney Island***Tucked away in Piney Island Just minutes from Assateague's nature trails and beach. Wireless internet and water access for canoe and kayak. Pet Friendly! New bedroom and bathroom added in 2013. All bedrooms on same level.***Bed Sizes: 1 Queen, 1 Double, 2...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Agape House1 / 15
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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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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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Island Sunrise1 / 13
    (2)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    Pet friendly
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    Smoking allowed
    Reviewed 23 September 2017
    Absolutely love Chincoteague and Island Sunrise. Such a pleasure dealing with ytour office. Love our trips and memoreis...til next year❤
    Reviewed 2 February 2014
    You should know that this is a duplex! We did not realize this and would not have been happy about it in peak season but the other half was empty so it was fine. I want to say...
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    About this property
    Island Sunrise is gorgeous 3 bedroom, 2.5 bathroom duplex home located in desirable Piney Island. Not only is this house pet friendly but it offers a deep water boat dock and 3 spacious decks. The views of Assateague Island and the Assateague Channel truly are second to none! Additional amenities...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Located very close to town, Bay Breeze will remind you of summer vacations as a child. This 3 bedroom, 2 bath homes sleeps 6 and has a washer & dryer, window a/c, and a ton of charm! Comfortable and affordable - this may be your spot at the beach! Additional amenities include: laundry: washer &...
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    Location Information
    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 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
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Lavinder House1 / 35
    (1)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    Pet friendly
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    Reviewed 3 weeks ago
    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, 4 Bathrooms, Sleeps 10
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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
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    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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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    The Bonnie Blue1 / 8
    (1)Terrible
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Terrace
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    Pet friendly
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    About this property
    ***7065 Wayne Road***Spacious rancher is pet friendly with large deck, fenced yard and internet.***Bed Sizes: 1 Queen, 1 Double, 1 Twin, 1 Double Sleep Sofa***2018 Rates:Prime Season Rates: $800 weekly/$160 per night.Off Season Rates: $650 weekly/$130 per night.Shoulder Season: $725 weekly/$145...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Hill House1 / 18
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Reviewed 13 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, 3 Bathrooms, Sleeps 9
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Terrace
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    Pet friendly
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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. Upstairs...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    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
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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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