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Chincoteague Island Vacation Rentals

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    Travelers to Chincoteague Island are booking July dates now. Secure your vacation rental today, and have the perfect trip.
    All 341 Rentals in Chincoteague Island
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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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    Sea Heart & Soul, Waterfront Memorial Park Rental1 / 32
    (7)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Waterman's Cottage1 / 21
    (36)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Beautiful Chincoteague Island retreat1 / 15
    (6)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Satellite TV
    • Porch
    • DVD Player
    • Parking
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    We greatly enjoyed our stay at this beach house. It was very neat and clean and had a fully stocked kitchen that met all our needs. The owner was very accommodating.
    Reviewed April 16, 2017
    This house was so nice and relaxing. Located on a cul de sac. Listen to nature on the patio. Cute ducks playing in the street. House felt very clean. The kids(and the adults...
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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
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    SA 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
    • Satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 7, 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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Grill
    • Satellite TV
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Tranquil Shores - Relaxation With a Water View1 / 30
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Grill
    • Waterfront
    • Satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 25, 2017
    Thank you so much Shawn and Joe for sharing your beautiful home with us and our dogs. We were two couples from DC looking for a local retreat out of the city with our dogs...
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    About this property
    Peaceful 3 bedroom/2 bathroom home located directly on Eel Creek. Appreciate the natural beauty of Chincoteague Island with gorgeous nature views from both the lower level screened in porch as well as the balcony off of the master suite. Enjoy relaxing mornings with the sunrise and breeze filled...
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Vacation House1 / 12
    (9)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Air Conditioning
    • Wi-Fi
    • Porch
    • Balcony
    • Grill
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 3, 2016
    Beautiful vacation home. Everything was exactly as listed. Peaceful and comfortable! The owner was very quick to respond to email and phone call. I would highly recommend...
    Reviewed September 21, 2016
    The house had a nice open layout on the downstairs. We had 2 families with three kids (4 year old, 3 year old, and 6 months old) and one other adult. We all fit nicely, the...
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    About this property
    5203 Wild Pony Court. Oyster Bay II community. 2 story house located on secluded cul-de-sac. 3 bedrooms, 2 1/2 bathrooms, kitchen, laundry, living, and dining rooms, screened porch, wrap around porch, handicapped ramp, master bedroom on main floor. Private back yard and parking. Located on the...
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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
    • Satellite TV
    • Private Yard
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 25, 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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    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Epiphany on Deep Hole Creek - Waterfront & Dock - late June still 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
    • Satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 12, 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 August 31, 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 Two weeks in late June available! Pets subject to approval and an additional fee. See Deep Hole Creek site for more info and photos.! Scroll down to email Blair & Martha (owners) . Or Call...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Duck's Delight - Your Seaside Home Away From Home!1 / 20
    (42)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 April 11, 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...
    Reviewed April 1, 2017
    What a wonderful little place to get away from it all for a few days! The owners are very friendly and respond almost instantly. We couldn't have chosen a better home to stay at...
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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
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Spacious, historic Chincoteague Is. vacation house1 / 13
    (6)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Reviewed November 9, 2016
    I can't tell you how much we enjoyed staying in this wonderful home. It had everything we wanted with the exception of a washer and dryer. It was spacious, warm and inviting. We...
    Reviewed August 26, 2016
    We rented this house for a week in August. Our extended family included myself, my husband, my two teenagers, and my mother and stepfather. The house (four bedrooms) had plenty...
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    About this property
    Totally updated but traditional "home away from home" facing the Chincoteague Channel on Chincoteague Island, minutes from the quaint downtown and the Assateague National Seashore and Wildlife refuge. Relax in this spacious, clean, and beautifully furnished home with water views of the sunset from...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 4 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
    • 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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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
    • Satellite TV
    • Hot Tub
    • Washer
    • DVD Player
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 22, 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 August 31, 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 !<BR> This house has extensive accomadations, two and a half bathrooms and an outdoor shower and foot washing station make as well as a private outdoor hot tub...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 4 Bathrooms, Sleeps 15
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Air Conditioning
    • Housekeeping Included
    • Ocean Views
    • 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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Studio, 3 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • Internet Access
    • Air Conditioning
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luxury waterfront home in Salt Marsh Landing. Spectacular sunsets. A long, private pier over the salt marsh leads you to a bay front dock area with shade. It's perfect for crabbing, fishing or canoe and kayak launching. Well appointed and architecturally pleasing, Castlebar features a main level...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bathrooms, Sleeps 10
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    Studio, 1 Bathroom, Sleeps 7 Quick View
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    • Internet Access
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    Pet friendly
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    Smoking allowed
    About this property
    Quaint and charming island cottage with all the amenities! Located on the southern end of the island, Daisey Cottage offers everything you'll need for an enjoyable vacation - central a/c, dishwasher, WiFi, washer/dryer and more. And it's even pet friendly! Additional amenities include: bedding 2:...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 1 Bathroom, Sleeps 7
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    Cowboy Cottage1 / 13
    (2)Very good
    Studio, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Balcony
    • Terrace
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 10, 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 St. 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 screened...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bathrooms, Sleeps 6
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    Assateague WATERFRONT CABANAS with a grand view!1 / 14
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Satellite TV
    • Terrace
    • Waterfront
    • Grill
    • Balcony
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 28, 2016
    This is the most beautiful and most peaceful setting ever. Close to everything but far enough to enjoy peace and quiet. Sitting by the water, enjoying the view and ocean breeze...
    Reviewed September 23, 2016
    I was just hoping for a nice place on the water to relax but this rental and location way exceeded my expectations. I really wanted to be close to the water and when we arrived...
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    About this property
    Our waterfront cabanas are located right on Assateague channel on East side Rd. The property overlooks Assateague Island and the National Park and the Wildlife Refuge. You can see the Assateague Lighthouse and the famous wild ponies straight from the property right across the water. You can wake...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Studio, 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
    Freshly updated Piney Island home with roots in island history. The kitchen and guest bedroom wing of this home were originally on Assateague Island, as part of the Assateague Village settlement! This pet friendly home boasts three bedrooms, large living and dining rooms, two full baths and a...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bathrooms, Sleeps 8
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    Studio, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Whispering Pines is a comfy 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, utilizing the sleep sofa in the living room. The open floor...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bathrooms, Sleeps 8
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    Agape House1 / 15
    (1)Excellent
    Studio, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 3, 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 - easy walking 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
    Rental Home - 2 Bathrooms, Sleeps 8
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    Lighthouse Estates #31 / 22
    (1)Excellent
    Studio, 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 June 28, 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 within walking distance to Memorial Park and Etta's Waterfront dining. The...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bathrooms, Sleeps 8
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    GORGEOUS 3BR  WATERVIEW "GINCOTEAGUE ESTATE"1 / 19
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Satellite TV
    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 11, 2017
    This full size residence is perfect for a family or a couple. It is spacious and clean and offers a water view as well as tons of privacy. It is located directly across the...
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    About this property
    This beautiful estate is nestled on a gorgeous, large yard on Chincoteague Island. It has just been renovated so now it's ready for you to come and enjoy it! This spectacular house offers a nice living room with 50 inch plasma TV, sun room, spacious kitchen, three bedrooms and two full bathrooms....
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    East Wing1 / 12
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Terrace
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    Pet friendly
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    About this property
    ***5159 Deep Hole Road***This charming island cottage built in 1920 features wood plank floors, open-beam ceilings, a screened-in porch and a large yard. Beautifully restored, East Wing is within walking distance of Little Oyster Bay, a boat launch, playground,restaurans and the best ice cream...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    June's Retreat1 / 33
    (1)Excellent
    Studio, 5 Bathrooms, Sleeps 12 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 17, 2016
    This is our 7th time vacationing in Chincoteague and June's Retreat was by far our favorite rental! We are a group of 12 and this spacious, beautifully decorated home easily...
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    About this property
    June’s Retreat is Chincoteague Island’s premier luxury vacation rental home, nestled on serene waterfront marshlands just north of town off of Main Street. This custom designed and decorated home leaves no detail unnoticed. From the bright spacious rooms with floor-to-ceiling windows to the...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 5 Bathrooms, Sleeps 12
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    Hidden Treasure1 / 20
    (1)Excellent
    Studio, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 25, 2016
    We stayed here a few weeks ago. We had stayed in another house on the same street in a previous year- have been coming to the island for decades! The AC is COLD, the deck...
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    About this property
    Escape to the beach - come to this wonderful "Hidden Treasure" nestled within one of Chincoteague Island's most prestigous communities. Hidden Treasure features a great open floor plan downstairs, as well as the privacy of a separate den (with sleep sofa), full bathroom and bedroom (2 twins). A...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***7469 Goose Lane***Very private and spacious waterfront home overlooking Assateague Island with pier and deep water dock. It offers over 1100 square feet of outside decking and large screen porch and over one acre prime waterfront setting overlooking marsh and beautiful vistas. Nice bedrooms...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Studio, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    Take a step back in time at this lovely little cottage. What you won't find are the modern-day "connectivity" features - there is no cable TV or internet. This is the perfect spot to disconnect and just enjoy your time at the beach! Prime Time is located in Piney Island;just a short distance from...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 1 Bathroom, Sleeps 6
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    Cockleshell Cottage1 / 14
    (2)Excellent
    Studio, 3 Bathrooms, Sleeps 8 Quick View
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    Reviewed May 24, 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 July 26, 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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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bathrooms, Sleeps 8
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    Studio, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Enjoy bay views and stunning sunsets from rocking chairs on the front porch and serene views over a tidal creek while dining on the back porch. This 3,000-square-foot, three-story home in the quiet, wooded neighborhood of Smuggler’s Cove is surrounded by loblolly pines and shares a boat launching...
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bathrooms, Sleeps 8
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    Admiral Benbow1 / 10
    (1)Excellent
    Studio, 3 Bathrooms, Sleeps 8 Quick View
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    Reviewed August 30, 2013
    My favorite vacation home ever! This house was beautiful and you get that "beach feeling" as soon as you pull in. The bay is within view from the house and the beach is...
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    About this property
    A very nice contemporary home located in Oyster Bay I. Located next to the community boat ramp - you have access to the water and the kids can fish and crab from the dock areas. This house has an outdoor ramp to the ground level. Don't miss out on the great screened porch for a family dinner. Bed...
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bathrooms, Sleeps 8
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    About this property
    Family-Friendly FUN -- This is a great rental home! The first floor offers a large living room that is open to the spacious eat in kitchen. Walk through the sliding glass doors from the kitchen out to your pond front patio with seating, a grill and beautiful views of wildlife that fills the pond....
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bathrooms, Sleeps 8
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    On Island Time1 / 21
    (1)Excellent
    Studio, 1 Bathroom, Sleeps 6 Quick View
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    Reviewed March 29, 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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    Wow... What a show piece! On Island Time is exactly what you expect in your beach rental, 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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    Chincoteague Island, Virginia 23336
    Rental Home - 1 Bathroom, Sleeps 6
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    Casa Bella1 / 15
    (3)Average
    Studio, 1 Bathroom, Sleeps 6 Quick View
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    Reviewed August 24, 2015
    My three middle aged friends and I spent a week on Chincoteague Island. Casa Bella is beautiful on the inside and the outdoor shower in back is wonderful. The location is...
    Reviewed July 8, 2013
    We booked our stay prior to the reading the other review. I worried the whole way to Chincoteague that we had made a mistake after reading that review. We could not have been...
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    About this property
    Very popular pristine beach bungalow located within a short walk to Main Street, downtown waterfront park, shopping and dining. Fully stocked kitchen, nicely landscaped yard, backyard deck, large outside shower (with hot/cold water), screen porch off the kitchen, large fenced back yard. New...
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    Chincoteague Island, Virginia 23336
    Rental Home - 1 Bathroom, Sleeps 6
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    Studio, 3 Bathrooms, Sleeps 10 Quick View
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    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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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bathrooms, Sleeps 10
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    Studio, 2 Bathrooms, Sleeps 10 Quick View
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    About this property
    Beautiful custom waterfront home in Oyster Bay. The open floor plan is bright and airy with plenty of room for everyone. The downstairs features an open living & dining room w/ gas fireplace, kitchen, and the master bedroom and bathroom. Upstairs you'll find the other 2 bedrooms and bathroom, as...
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    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bathrooms, Sleeps 10
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    Island Girl1 / 19
    (4)Very good
    Studio, 2 Bathrooms, Sleeps 10 Quick View
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    Reviewed September 17, 2015
    This was the perfect rental for our party. We had three couples and 4 kids. There are three beds, all queen, and the loft has four twins. The kids loved being in the loft...
    Reviewed August 31, 2014
    Nice quiet location. Home was clean and spacious however a little limited for eight with only two bathrooms. The kids did some successful crabbing from the bulkhead. We...
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    About this property
    Spacious waterfront home with water views from every window! The Great Room includes comfortable living and dining areas and a modern, fully stocked kitchen w/ breakfast bar. Amenities include central heat & air, private outside shower, wood stove, grill, screened porch and lots of deck space! New...
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    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bathrooms, Sleeps 10
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    Studio, 2 Bathrooms, Sleeps 8 Quick View
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    One of our newest Captain's Cove listings! Lakeside is a clean, comfortable home situated on a partially wooded lot that backs up to a wonderful lake. Guests can use the lake for canoeing and kayaking! You'll enjoy watching the ducks and geese in their natural habitat, and they'll even come up...
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    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bathrooms, Sleeps 8
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    Studio, 3 Bathrooms, Sleeps 10 Quick View
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    About this property
    Luxury waterfront townhome overlooking Chincoteague Bay. Beautiful sunsets. Long pier (shared) for fishing & crabbing, and enclosed porch (with a/c). Need more room? Book Sunset Dreams II or Bayside right next door! WIRELESS INTERNET is included with this unit. Pet friendly (with restrictions)....
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    ****4379 Ridge Road****Lovely 2 bedroom home conveniently located on Ridge Road, not far from Maddox Blvd, with many great island attractions. Perfect house for a family of 4! This house offers extra space in the large sunroom. Bright and airy, the sunroom works for both cool and warm weather. The...
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    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    ***3402 Ridge Road***Lovely 2 Bedrooms, 1.5 Baths duplex with water views. This duplex overlooks Assateague Island with great views for the Pony Swim. This is the Best way to watch the Pony Swim and not move from your porch! Sit and enjoy the views from 2 porches. The screened porch is off of the...
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    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    A Summer Place1 / 18
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Reviewed October 15, 2014
    The pics of the home make it appear very secluded. That is not the case. It is surrounded by 4 other homes with no direct access to the water. That being said - We had nice...
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    ***5094 Blake Point Road****Timeless Traditional home dates back to the turn of the century. Renovations have upgraded this fine 4 bedroom home that is also pet friendly and sleeps 10. Grand views of the Chincoteague Bay with large front screened porch and decks off both levels. Very quiet and...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Studio, 3 Bathrooms, Sleeps 8 Quick View
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    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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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bathrooms, Sleeps 8
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    Studio, 3 Bathrooms, Sleeps 6 Quick View
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    Poole's Cove manages to be tucked away right on Main Street. This home has been decorated with an artists' eye and poet's heart. The set up of this home offers plenty of room for the whole family, but enough distance for quiet moments to yourself. The Master bedroom suite is located in the main...
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bathrooms, Sleeps 6
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    Saltings1 / 24
    (2)Excellent
    Studio, 3 Bathrooms, Sleeps 8 Quick View
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    Reviewed July 15, 2016
    We spent a very relaxing week on Chincoteague island at this beautiful house. The neighbours offered to take our boys out crabbing which they greatly enjoyed. We loved the...
    Reviewed April 21, 2016
    We stayed for a week at this house in the summer of 2015, and had a wonderful time. The bedrooms were all very comfortable, and we had many at-home dinners enjoying the...
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    Saltings is a stunning custom-designed bayfront home with sweeping panoramic views over Chincoteague Bay. The home has an open floor plan designed to capture these breathtaking water views from every room. Saltings is nestled at the edge of a salt marsh where indigenous wildlife is abundant and...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bathrooms, Sleeps 8
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    Studio, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    Enjoy some of the island's best water views overlooking Oyster Bay from nearly every room of this custom beach home! Located on a bulk-headed waterfront lot in Richardson's Landing, you can fish and crab from the backyard! A wonderful feature of this spacious home is that you'll find your bedrooms...
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    Chincoteague Island, Virginia 23336
    Rental Home - 4 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    ****6206 Marsh Island Drive Unit #1***Wonderful effiencency condo unit located on Marsh Island. Enjoy some of the best water views and sunsets on Chincoteague. Fully equipped effiencincy kichen and laundry area. Shared pier and waterside picnic area. Comfortable and affordable with private...
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    Chincoteague Island, Virginia 23336
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    ***5323 Hibiscus Drive-Oyster Bay I*** This spacious pet friendly home is located in the private community of Oyster Bay II. Enjoy your morning coffee from the large deck or screened porch. Wildlife abounds with deer, rabbits, ducks, geese, and lots of songbirds in this quiet retreat! Enjoy...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tall Pines1 / 8
    (2)Excellent
    Studio, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed 1 week ago
    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 August 29, 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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    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bathrooms, Sleeps 6
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    Island vacation rentals - seaside villas, waterfront homes and condos

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

    Abundant outdoor recreation and attractions

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

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

    Leisurely shopping and dining

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

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

    Villa and home rentals – the perfect seashore vacation choice

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

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