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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 342 Rentals in Chincoteague Island
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    Waterman's Cottage1 / 21
    (35)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 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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    Beautiful Chincoteague Island retreat1 / 15
    (6)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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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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    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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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, 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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    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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    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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    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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    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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    • Wi-Fi
    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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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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
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    • Satellite TV
    • Hot Tub
    • Washer
    • DVD Player
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    • 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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    Agape House1 / 15
    (1)Excellent
    Studio, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Air Conditioning
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 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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    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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    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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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Satellite TV
    • Patio
    • Grill
    • Washer
    • Waterfront
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    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
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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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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    Studio, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Balcony
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***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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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    ***6201 Ocean Blvd***Bring your four legged friend to this well-appointed home within walking distance to restaurants, shops, and more! This is a great pet friendly house right in the heart of downtown. It offers DSL Wi-Fi and a fax machine in the separate sitting room off of the living room. The...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Studio, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    As a classic Chincoteague-style home, Hopkin's House is situated on the East Side of Chincoteague Island and overlooks the Assateague Channel. You'll enjoy a wonderful, relaxing vacation at this 3 bedroom home; it's just a short distance from the public boat ramp, Memorial Park, a restaurant and...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bathrooms, Sleeps 7
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    Studio, 4 Bathrooms, Sleeps 11 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    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
    Rental Home - 4 Bathrooms, Sleeps 11
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    On Island Time1 / 21
    (1)Excellent
    Studio, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    About this property
    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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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***7141 Wayne Road***Welcome to Blue Pearl Cottage, a lovely, sunny beach house, just minutes from fabulous beaches, wildlife and the quaint downtown of Chincoteague. This airy cottage nestled beside pine woods has a large wrap-around deck, a screened porch and offers privacy and quiet, with all of...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pearl in the Pines1 / 11
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Reviewed May 7, 2017
    My family of 4 stayed here. We enjoyed the open floor plan, the large dining room table and that everything is on one level, the shower in master bedroom was not very spacious...
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    About this property
    ****5476 Pearl Drive-Oyster Bay I***Lovely home located in private community with water view and next to boat ramp. WiFi Available. Nearby is DeColores in the Pines.*** Bed Sizes: 2 Queen, 2 Twin, 1 Queen Sleep Sofa***Prime Season Rates: $1050 weekly/$210 per night.Off Season Rates: $750...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Studio, 1 Bathroom, Sleeps 7 Quick View
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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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    Studio, 4 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Enjoy some of the island's best water views overlooking Oyster Bay from nearly every room of this custom beach home! Located on a bulk-headed waterfront lot in Richardson's Landing, you can fish and crab from the backyard! A wonderful feature of this spacious home is that you'll find your bedrooms...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 4 Bathrooms, Sleeps 8
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    Misty's Thicket1 / 13
    (1)Very good
    Studio, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Lovely townhome rental features TWO great screened porches! One with a ceiling fan just off living room, large bedrooms, including a master bedroom suite, second-level screened porch off one bedroom and an outside shower. A full ensemble of appliances, central air, galley-style kitchen, water...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 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
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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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    Hill House1 / 14
    (1)Excellent
    Studio, 3 Bathrooms, Sleeps 10 Quick View
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    Smoking allowed
    Reviewed September 13, 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
    Rental Home - 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
    About this property
    ***6703 Megan Lane***Bright and spacious duplex located on private lane. In walking distance of many island attractions. Offers second floor master bedroom suite. 1 bedroom and 1 bath downstairs/1 bedroom and 1 bath upstairs. Nearby is Georges Retreat.***Offering WiFi***Bed Sizes: 1 Queen, 1...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Studio, 3 Bathrooms, Sleeps 8 Quick View
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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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    About this property
    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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    Southern Dream1 / 14
    (1)Excellent
    Studio, 2 Bathrooms, Sleeps 8 Quick View
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    Reviewed March 12, 2016
    My family has stayed at this rental for the last few summers when we go to Chincoteague. My favorite thing here is the view of the water from the deck. We love cooking out...
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    About this property
    Charming 3 bedroom ranch home located in one of Chincoteague Island's finer residential communities. Nice, quiet location with a water view of Oyster Bay. Spend your time outside on the spacious deck or screened porch - there's plenty of room for all! Many modern amenities such as central air, high...
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    Chincoteague Island, Virginia 23336
    Rental Home - 2 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
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    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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    Edie's Folly1 / 20
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • DVD Player
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    Reviewed July 27, 2014
    My husband and I took our 3 teenagers for our 8th visit to Chincoteague. It was our first time staying at Edie's Folly, located in Piney Island, the neighborhood closest to...
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    About this property
    ***6404 Pine Drive-Piney Island***Nature lover’s dream! Tucked away in Piney Island with Assateague just a short bike ride away . You’ll love relaxing in the large screen porch or enjoy the water views from the second level deck. Community boat launch great for kayakers. Sleeps 9, screen porch, 2...
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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 above...
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 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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    Studio, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Wow, what a deal! This magnificent 5 bedroom, 3 bathroom waterfront home is perfect for your family vacation. Offering two first floor bedrooms one with a twin trundle bed and en suite bath, the second bedroom has a double bed. The large open rooms that sprawl the first floor include two spacious...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    ****4379 Ridge Road****Lovely 2 bedroom home conveniently located on Ridge Road, not far from Maddox Blvd, with many great island attractions. Perfect house for a family of 4! This house offers extra space in the large sunroom. Bright and airy, the sunroom works for both cool and warm weather. The...
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    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Cockleshell Cottage1 / 14
    (2)Excellent
    Studio, 3 Bathrooms, Sleeps 8 Quick View
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    Reviewed 4 weeks ago
    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 6 Quick View
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    About this property
    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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    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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    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bathrooms, Sleeps 8
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    Cowboy Cottage1 / 13
    (2)Very good
    Studio, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Shared Outdoor Pool (Unheated)
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    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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    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    ***6138 Fir Landing***Located just steps away from Fir Landings Public Boat Launch, this spectacular property is sure to please the boater in your family with its quick and easy access to Little Oyster Bay. 2 first level bedrooms and 2 second level bedrooms, with a large open floor plan makes this...
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    Chincoteague Island, Virginia 23336
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    An Unfettered View1 / 25
    (5)Excellent
    Studio, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Reviewed 4 weeks ago
    We try to visit the Eastern Shore near Assateague once a year in May before the summer crowds come in. We'd usually tent camp at Assateague seashore or Toms Cove but this year...
    Reviewed September 12, 2016
    This place is absolutely EVERYTHING you could hope for on vacation. The home is immaculately clean and lots of room. The well-kept , private dock is an exciting and successful...
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    About this property
    This beautiful 2BR ranch home has a quiet, out-of-the-way location on little Oyster Bay. The views of the bay are beautiful and expansive with a long pier straight from the back deck its perfect for crabbing, kayaking & canoeing. An Unfettered View features all amenities including a private master...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Air Conditioning
    • Housekeeping Included
    • Ocean Views
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    • Waterfront
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    Pet friendly
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    About this property
    SEA HARBOR: 1 mile from Assateague Island and 5 miles from beach front fun. Check-In 4pm Check-Out 12pm. This home offers large open spaces, a cozy, clean and comfortable place to stay along with amazing adventures for everyone to explore. It is furnished with many necessities so you can rest,...
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Nestled beneath the tall pines is where you'll find this delightful Piney Island home. The Bird House features an open living room/kitchen/dining area, and extra "family" space in the private den. The many large windows throughout the home create a bright, airy atmosphere. Enjoy relaxing breezes on...
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    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bathrooms, Sleeps 8
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    About this property
    Bayside II is a nearly new, well appointed, waterview, 3-bedroom duplex located just off of South Main St. on the quiet southern end of the island. This spacious, nearly 2,000 sq ft. home offers a family of up to 8 an open floor plan to enjoy the whole gang without being cramped into a small area....
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bathrooms, Sleeps 8
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    Heron's Cove On Salt Meadow1 / 16
    (1)Excellent
    Studio, 5 Bathrooms, Sleeps 10 Quick View
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    About this property
    Peaceful and stunning waterfront home! Located on a quiet side-street, Heron's Cove features a reverse floor plan with all bedrooms on the first floor, and the main living-level on the second floor. This allows you to capture and maximize the fabulous bay views! The second floor also features a...
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    Chincoteague Island, Virginia 23336
    Rental Home - 5 Bathrooms, Sleeps 10
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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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