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Chincoteague Island Vacation Rentals

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    Travelers to Chincoteague Island are booking September dates now. Secure your vacation rental today, and have the perfect trip.
    All 257 Rentals in Chincoteague Island
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    Vacation House1 / 12
    (22)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Jay’s Retreat:  Kayaker’s Delight w/use of 2 kayaks-Pets Considered1 / 22
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Beautiful Chincoteague Island retreat1 / 15
    (17)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Waterfront, 5 BR, 4 BA, Elevator, sleeps 101 / 48
    (1)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Patio
    • Grill
    • Washer
    • Waterfront
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 12, 2017
    Our family loved this home. It was spacious, comfortable, well appointed and oh that view. I ( the family chef) was very pleased with the state-of-the-art kitchen...I didn't...
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    About this property
    The Moorings North is an unique architecturally designed luxury 5 bedroom home in the heart of Chincoteague Island. The house is elegantly decorated and has mesmerizing panoramic views of Chincoteague Bay. It is conveniently located in walking distance to small shops, a coffee house, and...
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    Chincoteague Island, Virginia 23336
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Sweet Retreat:  Charming Cottage-Great for Family or Romantic Getaway1 / 28
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Patio
    • Private Yard
    • Wi-Fi
    • DVD Player
    • Grill
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 19, 2019
    Sweet Retreat has everything you need for a peaceful and comfortable stay. The cottage has all you need to enjoy yourself. Clean is the word and I would suggest the linen rental...
    Reviewed April 8, 2019
    The Sweet Treat was exactly that - Sweet! It has so much room inside and was so clean and comfortable that we did not want to leave. Thank you for providing all the amenities...
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    About this property
    Sweet Retreat is part of of the owner managed properties of O'Connor Properties. We have hosted over 150 guests in Sweet Retreat over the last 3 years and have graciously received many five star reviews. * Perfect for a romantic getaway * 3 bedrooms, 2 bath, marsh-view home, located in...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sunset Bay Villas Chincoteague Island - Sunset in Paradise1 / 24
    (8)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 30, 2018
    This property was perfect for our family (family of 4 plus 2 grandparents). Annie was a pleasure to work with right from the beginning. Payment schedule was reasonable and...
    Reviewed February 26, 2018
    We stayed in Sunset in Paradise for a week a few years ago and absolutely loved it (and rented again for summer 2018)! The owners are very responsive, hospitable, and helpful in...
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    About this property
    ANOTHER DAY IN PARADISE CHINCOTEAGUE BEAUTIFUL BAY FRONT CONDO WITH AMAZING WATER VIEWS Owner operated by: Annie Switzer Call 240/498/0074 *** Booking 2019 *** PLEASE CONTACT OWNER WITH QUESTIONS BEFORE BOOKING Unit 213 - 'Sunset in Paradise' at Sunset Bay Villas *** Please see FKN 7097918...
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    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Spacious, historic Chincoteague Is. vacation house1 / 13
    (14)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Yard
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 3, 2019
    This was a beautiful, comfy home and a great price for a 4 bedroom water view Main Street home. The kitchen was fully stocked and had a gas stove, dishwasher, toaster oven. We...
    Reviewed June 30, 2019
    Lots of space though not too large, it retains intimacy. Well equipped kitchen, and we all felt the beds were extremely comfortable. On the down side, it would have been nice...
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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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    Lighthouse Estates #31 / 22
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 14, 2017
    The location was great, watching the lighthouse at night was amazing. The pool was wonderful to have and well cared for.
    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 just a short distance to Memorial Park and Etta's Waterfront dining. The...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Tranquil Shores - Relaxation With a Water View1 / 30
    (11)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Grill
    • Waterfront
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 26, 2018
    Wow! Exceptionally close (walking distance) to both Assateague National Wildlife Refuge AND family friendly activities, such as bike shops and eateries. Very quiet...
    Reviewed July 19, 2018
    Communication with the owner was great. The house was in a convenient location near downtown on a very quiet street. The kids were able to ride their bikes there safely. We...
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    About this property
    Peaceful 3 bedroom/2 bathroom home located directly on Eel Creek. Appreciate the natural beauty of Chincoteague Island with gorgeous nature views from both the lower level screened in porch as well as the balcony off of the master suite. Enjoy relaxing mornings with the sunrise and breeze filled...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cedar Cove1 / 25
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 15, 2019
    Staying @ Cedar Cove definitely enhanced our week-long visit to Chincoteague Island. We enjoyed sitting out on the spacious deck every morning (& evening) watching birds...
    Reviewed July 22, 2018
    Cedar Cove was a great place to stay. It was fully equipped with everything we needed and was right along Oyster Bay. It was also very close to everything. Would definitely stay...
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    About this property
    Beautiful custom waterfront home in Oyster Bay. The open floor plan is bright and airy with plenty of room for everyone. The downstairs features an open living & dining room w/ gas fireplace, kitchen, and the master bedroom and bathroom. Upstairs you'll find the other 2 bedrooms and bathroom, as...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    A Getaway1 / 20
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 19, 2018
    We recently stayed at A Getaway this year. It was perfect for the two of us (retired couple). The house was spacious and very clean. Housekeeping staff had done a great job! We...
    Reviewed May 19, 2018
    This house is located just off the Main road about a mile from town in a quiet community. Very clean with everything one might need. Well furnished and decorated it is an ideal...
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    About this property
    A Getaway is a bright and cozy home nestled between pink Crape Myrtles in the private, secluded neighborhood of Oyster Bay II right off of North Main Street. This home features a 12 x 24 screened in deck that is perfect for outdoor gatherings, dinners, and making memories. With clean, functional...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Red Cedar1 / 27
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • DVD Player
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 10, 2017
    Comfortable 3 bedroom house surrounded by nature. At various points we saw herds of goats, llama, or ponies, raccoons, opossum, a variety of birds, and at night the chatter of...
    Reviewed September 30, 2016
    My wife and I stayed here in early September, 2016 for four nights to go kayaking and explore the area. The house worked very well for us. The beauty of the Red Cedar is the...
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    About this property
    Nature calls at this nicely appointed 3 bedroom rental home! Red Cedar is nestled on the edge of a huge expanse of nature preserve-type land where you'll see all types of native wildlife. Birders bring your life list. The home features modern amenities, offers a first floor bedroom, full laundry,...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Grey Heron is an amazing contemporary waterfront home nestled on the shoreline of Chincoteague Bay. You'll love the floor plan; a terrific great room with wood floors flanked by a kitchen on one side and a fireplace on the other. And great windows throughout! There's also a 'sitting room' with...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sunset Bay Villas - Another Day in Paradise1 / 33
    (11)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Washer
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 31, 2018
    We very much enjoyed our time here. We are long time visitors in Chincoteague but this was our first rental as opposed to booking separate hotel rooms for the family. We were...
    Reviewed August 30, 2018
    The location of this condo is amazing. You have gorgeous views of the bay from the living room - dinning room area and the master bedroom. The sunsets were amazing. We liked...
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    About this property
    ANOTHER DAY IN PARADISE CHINCOTEAGUE BEAUTIFUL BAY FRONT CONDO WITH AMAZING WATER VIEWS Owner operated by: Annie Switzer Call 240/498/0074 *** Booking 2019 *** PLEASE CONTACT ME WITH QUESTIONS BEFORE BOOKING Unit 103 - 'Another Day in Paradise' Unit 213 - 'Sunset in Paradise' 2nd Floor...
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    Location Information
    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cockleshell Cottage1 / 25
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 23, 2018
    This home by far was the best rental we have had yet. From the quiet peaceful area to the wildlife seen just from the backyard. Close enough to enjoy walking to the shops or...
    Reviewed 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...
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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 modern 3 bedroom, 3 bathroom home boasts a first-floor master bedroom suite (Queen), all amenities and comfortable furnishings. Upstairs...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Windrush1 / 38
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 1, 2018
    Looking for a secluded gem to get away for a few days? We were and this place fit the bill to a T! From the huge wrap-around deck, to the comfortable beds, the Windrush was the...
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    About this property
    Our guests come year after year to relax and enjoy truly fabulous views of our famous Chincoteague Bay sunset! This roomy, attractively decorated home is surrounded by water views, wetlands and birds! Windrush boasts lots of outdoor space including two screened porches, open decks/balconies and a...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Duck's Delight - Your Seaside Home Away From Home!1 / 21
    (47)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 3 weeks ago
    Duck's Delight has it all; it's clean, spacious, comfortable, affordable, and peaceful! It is located on a street with other houses around, yet it is so quiet and relaxing. The...
    Reviewed May 5, 2018
    This house is a 5 star! Great location people! Very neat, clean and cozy. Beds are comfortable, kitchen has everything you need to cook and a screen porch to relax. Price is...
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    About this property
    Duck's Delight is our home in America's Happiest Seaside Town (2014 Coastal Living)! 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 eastern shore of Virginia. Central air, newly updated and...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Morning Memories1 / 21
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 2, 2018
    We love staying in Lighthouse Estates and love Morning Memories! We enjoy bringing our dogs and like that it is pet friendly! We have everything we need there and the kitchen...
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    About this property
    A light, bright and airy beach rental with community pool and water access with shared dock. The spacious 2 bedroom, 2.5 bathroom home is tastefully furnished and features all appliances including washer/dryer and dishwasher. Wireless internet is included. Come and enjoy a great stay! Additional...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sea Heart & Soul, Waterfront Views, Pier and Playground at this Park Rental!!!1 / 24
    (13)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Waterfront
    • Ocean Views
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    This trip was a special birthday gift for my granddaughter who is passionate about horses! The owner took special time to leave a birthday basket and vase for her when we...
    Reviewed May 30, 2019
    This was truly a home away from home. Everything was comfortable, well decorated, and had everything we needed. We hope to return in the future!
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    About this property
    Sea Heart and Soul next to Sea Adventure and Soul are 2 miles from Assateague Island and 5 miles from beach front fun. AT $229.00 per night this Rental offers open spaces, a cozy, clean and comfortable place to stay along with amazing adventures for everyone to explore. Located just minutes from...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    On Island Time1 / 20
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • DVD Player
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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 home, from the bright and fun decor to the spacious and bright floor plans, all of this wrapped in a traditional Eastern Shore Home. The front enclosed porch is great for reading or just relaxing in the afternoon...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Epiphany on Deep Hole Creek - Waterfront & Dock -wow!1 / 31
    (44)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Ocean Views
    • Patio
    • DVD Player
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 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 Pets subject to approval and an additional fee. See DeepHoleCreek s ite for more info and photos.! Scroll down to email Blair & Martha (owners) . Or Call Blair & Martha at the number listed for...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Sea Adventure: Waterfront  Views, Pier and Playground at this Park Rental!!!1 / 20
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Ocean Views
    • DVD Player
    • Washer
    • Air Conditioning
    • Waterfront
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 20, 2018
    This was a lovely three bedroom house that was just perfect for us and our two young kids. With or without kids the location is very good, close to Main Street and a quick ride...
    Reviewed 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. At $229.00 per night this Rental offers open spaces, a cozy, clean and comfortable place to stay along with amazing adventures for everyone to explore. Located just minutes from Assateague...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Mermaid Crossing1 / 22
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 10, 2018
    This location was an unexpected delight! More than any one particular thing, it was comfortable! We will be returning!
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    About this property
    Comfortable, pet friendly home on large, side-creek lot with fantastic views from both the front and back of house! Excellent crabbing from dock! (Property sits on creek only suitable for kayaks, canoes and crabbing.) Just a short distance to Memorial Park and Fairgrounds. 2 living room areas, 2...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Island Sunrise1 / 30
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 23, 2017
    Absolutely love Chincoteague and Island Sunrise. Such a pleasure dealing with ytour office. Love our trips and memoreis...til next year❤
    Reviewed February 2, 2014
    You should know that this is a duplex! We did not realize this and would not have been happy about it in peak season but the other half was empty so it was fine. I want to say...
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    About this property
    Island Sunrise is gorgeous 3 bedroom, 2.5 bathroom duplex home located in desirable Piney Island. Not only is this house pet friendly, but it offers a deep water boat dock and 3 spacious decks. The views of Assateague Island and the Assateague Channel truly are second to none! Additional amenities...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Saltings1 / 21
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    About this property
    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 - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Daisey Cottage1 / 15
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Reviewed July 21, 2018
    This cottage was adorable and had everything we needed. It made our beach vacation absolutely wonderful! The layout was open and the decor was adorable. The master bedroom...
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    About this property
    Quaint and charming island cottage with all the amenities! Located on the southern end of the island, Daisey Cottage offers everything you'll need for an enjoyable vacation - central a/c, dishwasher, WiFi, washer/dryer and more. And it's even pet friendly! Additional amenities include: 4 pets max....
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    Panorama1 / 21
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Reviewed April 8, 2012
    My husband and I had a wonderful weekend on Chincoteague staying in Panorama. We have stayed many places on the island over the years, and this was just fantastic. Right...
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    About this property
    Tastefully appointed first-floor condo situated on the Assateague Channel. Enjoy the unobstructed views of the channel and Assateague Lighthouse! Master bedroom suite with doors to waterside deck area, screened porch, open floor plan and more. Recently updated and refreshed, this is a great unit!...
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    Chincoteague Island, Virginia 23336
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Channel Lookout1 / 26
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • DVD Player
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 30, 2018
    This house was perfect for our family. It is in a convenient location and the house self is very comfortable.
    Reviewed June 2, 2018
    Nice duplex. All rooms accept bathroom face the Assateague Channel. Very quiet location. Great setup for two friends. One twin headboard needs to be tightened. Ceiling fans in...
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    About this property
    This property has a location that is rich with amenities. Situated right next to Memorial Park, you can sit on the deck and enjoy the water views as the kids run, play, skateboard, fish and crab. The first floor is an open room consisting of the kitchen, dining area and living room (with queen...
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    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Water's Edge1 / 34
    (5)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
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    • Waterfront
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    Pet friendly
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    Reviewed May 24, 2017
    Water's Edge is in a great location - right on the water and close enough to walk into town. The house was clean and equipped with anything you might need. As mentioned in...
    Reviewed October 17, 2016
    This recently renovated home features an open floor plan with wrap around windows facing out to the water. The small watch tower at the top of the house has stunning views and...
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    About this property
    Water's Edge is an adorable Bay Front cottage in walking distance to Chincoteague's Historic Downtown. You'll be impressed by the charm of this home from the time you pull in the driveway. On the first floor you'll find a full bathroom with an open great room with expansive bay views. There is a...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    Serendipity1 / 20
    (2)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    Come stay in this classic Eastern Shore Style home. Located just a few blocks from our famous downtown Main Street area, you are within walking distance to most of our shops and restaurants. Serendipity has a very nice screened porch for those memorable Chincoteague Summer evenings. This home also...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    • Shared Outdoor Pool (Unheated)
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for a fun place for a family vacation? Look no further! Blue Diamond offers all amenities: community pool, shared water access, comfortable furnishings and high speed internet (just to name a few). And if that's not enough, Blue Diamond is located on the popular East Side of the island...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Charlotte's Morning Sun1 / 26
    (2)Average
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Terrace
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    Pet friendly
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    Smoking allowed
    About this property
    Set in the boutique residential community of Oyster Bay II, ‘Charlotte's Morning Sun’ is a stunning 5-star waterfront home that offers unobstructed water views and breathtaking vistas of Oyster Bay. Flowing generously over two levels, Charlotte features 4.5 bathrooms and 4 light-filled bedrooms,...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    Completely renovated 2 bedroom, 1 bath waterfront condo! (Most pictures listed are prior to renovation.) This second floor unit has breathtaking views of the lighthouse, wildlife, and of course, the ponies. Sea Tag's brand new deep water dock is the best on the island. Boat slip included with...
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    Location Information
    Chincoteague Island, Virginia 23336
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    June's Retreat1 / 37
    (1)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Grill
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    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 - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    Joint Venture1 / 23
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed June 19, 2018
    We enjoyed a quiet, lovely view out of the back of the house. We were very comfortable in the house. The kitchen was simple, but stocked enough for our needs. The rooms are...
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    About this property
    Joint Venture is the perfect townhouse for an affordable vacation! Take a short stroll or bike ride to ice cream, mini golf or any of the shops on Maddox Blvd. Bike or drive to the beach from the property! Joint Venture offers a water view of Little Oyster Bay (tidal creek) that can be enjoyed any...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    As one of our newest vacation rental listings, we're pleased to be able to offer you 'A Sunshine Cottage'! With all the charm of a Chincoteague-style cottage, you'll be reminded of the days gone by. The front porch is the perfect spot to relax with a cool drink and book, and the convenient in-town...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Sunset Bay Villa 1091 / 25
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 17, 2015
    Rental is clean and spacious. Had an absolutely lovely family vacation and no regrets on splurging on this condo! Condo is well equipped with up to date appliances, and staying...
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    About this property
    This beautiful ground-level villa boasts five-star amenities including a private deck off the living room area with a walk-out to the marina. Enjoy this master bedroom suite, with private bath that features a jetted tub to relax in and a private exit to the waterside deck area. The gourmet kitchen...
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    Location Information
    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Drop Anchor1 / 22
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Reviewed May 15, 2018
    Nice house with all amenities you need available. Location is convenient for putting a boat in at Curtis Merritt Harbor or at other town ramps. Quiet, clean, beautifully...
    Reviewed November 15, 2017
    This place has such a nice flow to it. Everything you need for a relaxing time on the Island. Fishing within walking distance. Loved it, wished I could have stayed...
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    About this property
    'Drop Anchor' is a luxury rental home nestled on a quiet cul-de-sac beneath the tall pines. All amenities including a great open kitchen, screened porch, wireless internet, gas fireplace and bedrooms on both levels. The upstairs master bedroom suite is spacious and inviting, and this home features...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cowboy Cottage1 / 18
    (4)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Reviewed July 3, 2018
    This was within walking distance of dollar general and some other shops, only a couple of miles from the beach!House was perfect!!!How was pet friendly and clean! lots of room...
    Reviewed August 7, 2017
    I found Chincoteague Island an enjoyable vacation destination. The Cowboy Cottage is a comforortable, somewhat rustic place to stay. It's central location on the island makes...
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    About this property
    Cowboy Cottage is a pet friendly home conveniently located a block from Maddox Blvd., and just a couple of blocks from downtown Main Street. This ranch-style home has an open floor plan and is handicap accessible with a ramp to enter the house and bedroom/bathroom accessibility. There is a large...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Wildflower1 / 34
    (1)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 18, 2018
    Overall this was a really nice place. It is on a quiet street, has a really nice large backyard and private dock. The kids loved playing there and fishing/crabbing from the dock...
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    About this property
    Beautiful waterfront home with shared pier plus floating dock on deep water!! Ground level is a large screened patio perfect for those summer time seafood feasts. The first level is great room boasting reclaimed barn board walls and wide plank pine floors with a separate den and full bath. There is...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Sundance at Marsh Island1 / 16
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Reviewed July 22, 2018
    This was my 1st time visiting Chincoteague Island. I can honestly say I will be back next year. We stayed the second week of July, we had beautiful weather. If you are looking...
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    About this property
    Nestled on the tip of Marsh Island, this fabulous 2 bedroom townhome features spectacular views of the Chincoteague Bay. Watch the fishing boats go by and witness the million dollar sunsets everyone talks about - all from the comfort of your own vacation home! The open floor plan downstairs is very...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Lavinder House1 / 44
    (1)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    Reviewed November 16, 2017
    This gerrymandered Victorian is the almost perfect weekend get-a-way rental - except . . . Of the five bedrooms, there is only one that you can get to without climbing steep and...
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    About this property
    Tucked away off North Main on the waterfront, Lavinder House is a charming Victorian-style home steeped in tradition. From the original woodwork to the brick kitchen floor, you'll enjoy the original integrity this island home features. Once the home of actress Linda Lavin, Lavinder House tells its...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Family Affair1 / 21
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Smoking allowed
    Reviewed 2 weeks ago
    While looking for a two bedroom vacation rental how lucky we were to find Family Affair.Overall a great townhouse in great shape, well kept and pretty much has everything you...
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    About this property
    Located on the southern end of the island, Family Affair is a town home with gorgeous views of tidal canal in the backyard easily viewed from both stories, including the spacious second-level balcony. Enjoy the water access (tidal canal) and surround yourself in nature from the shared pier, just...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Assateague Light1 / 19
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
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    Reviewed August 25, 2012
    Assateague Light is a very nice first-floor waterfront condo facing the Assateague Channel. The view from the deck is spectacular. When we were looking for vacation rentals on...
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    About this property
    This modern 2 bedroom condo located on the first floor features a master bedroom suite with a king bed, private bath and sliding glass door to the waterfront deck. The second bedroom has two twin beds with a full bathroom across the hall. This shared bath offers a walk in shower and washer/dryer....
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    Location Information
    Chincoteague Island, Virginia 23336
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sea Tag #221 / 19
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Reviewed August 12, 2015
    Nicely remodeled 2 BR/1 BA Condo. Great view of Assateague Island & the lighthouse. Perfect for pony penning & bring your binocs to view the ponies year round. Rental...
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    About this property
    We are pleased to be able to offer you this fabulous 2nd level unit! The interior has been completely renovated, from the drywall and paint, to the furniture! You'll enjoy all modern amenities including flat-screen TVs (3), internet, washer/dryer facility and updated kitchen (appliances, cabinets,...
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    Location Information
    Chincoteague Island, Virginia 23336
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Misty's Thicket1 / 16
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Reviewed September 28, 2017
    Our family's second visit to Misty's Thicket was just as perfect as our first. Very comfortable house and the dock for crabbing is where we spend most of our time. We caught...
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    About this property
    Located on South Ridge Road, this lovely town-home features a private pier, central air conditioning, and galley style kitchen complete with a dining area and all necessary appliances. The cozy living room leads you onto one of two screened in porches perfect for unwinding with family and friends....
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Enjoy one of the most amazing, unobstructed views of Assateague Bay and Island from the comfort of your own waterfront deck and balcony! Watch the ponies in the distance on the island, abundant waterfowl, or maybe even catch a glimpse of dolphins in the bay. Two kayaks are also provided if you...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    About this property
    Aptly named, you'll enjoy a nice relaxing vacation at 'Tranquil Escape!' As one of the newest additions to the vacation rental market, this home is located in a quiet residential neighborhood and features expansive porches and outdoor areas for you to enjoy! With 4 bedrooms, 3.5 bathrooms, an...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    As one of our newest vacation rental offerings, we're pleased to be have this downtown charmer! Shreiner's Tradition is a renovated 2+ bedroom home located just outside the downtown area. Enjoy walking to restaurants, shopping, ice cream and the movie theater! This home features an eat-in kitchen,...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Enjoy some of the island's best water views overlooking Oyster Bay from nearly every room of this custom beach home! Located on a bulk-headed waterfront lot in Richardson's Landing, you can fish and crab from the backyard! A wonderful feature of this spacious home is that you'll find your bedrooms...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Additional Chincoteague Island Info

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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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