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Holiday Homes near Proud Mary Charters

7171 Mason Dr, Chincoteague Island, Virginia 23336-1922
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    Travellers to Chincoteague Island are booking April dates now. Secure your holiday rental today, and have the perfect trip.
    All 100 Rentals in Chincoteague Island
    Sea Adventure: Waterfront  Views, Pier at this Park Rental!!!1 / 19
    (2)Excellent
    0.8 kilometres from Proud Mary Charters
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Sea Heart & Soul, Waterfront Memorial Park Rental1 / 32
    (11)Excellent
    0.8 kilometres from Proud Mary Charters
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Cozy cottage near Old town Fishing Village1 / 12
    (2)Very good
    0.9 kilometres from Proud Mary Charters
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Tranquil Shores - Relaxation With a Water View1 / 30
    (11)Excellent
    1.1 kilometres from Proud Mary Charters
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Grill
    • Waterfront
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 July 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 19 July 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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    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beautiful Chincoteague Island retreat1 / 15
    (18)Very good
    1.0 kilometres from Proud Mary Charters
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Porch
    • DVD Player
    • Parking
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Cute little neighborhood off Main Street. It's an easy walk to the shops and restaurants downtown. Of course, the main attraction for us is always the beach at Assateague. We...
    Reviewed 5 September 2018
    Nice location walking distance to town and to the pier for fishing. Located on a quiet street. House was cozy and decorated nicely.
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    About this property
    Come stay and relax at this quiet retreat. This listing is a newly remodeled home which is tastefully decorated. There are three color themed bedroom's; which have two queens and two twin sized beds. There is serenity all around you, come sit on the screened in porch and relax while listening to...
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    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Duck's Delight - Your Seaside Home Away From Home!1 / 19
    (46)Excellent
    1.2 kilometres from Proud Mary Charters
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Grill
    • DVD Player
    • Wi-Fi
    • Patio
    • Parking
    • Porch
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 May 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...
    Reviewed 13 December 2017
    We had a wonderful time at duck's delight. The house was great and the ducks even came to visit one morning. It was awesome!!! Thanks so much,The Frey's
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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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    Chincoteague Island, Virginia
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Dancing Water View1 / 9
    (2)Excellent
    0.6 kilometres from Proud Mary Charters
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 2018
    This place is spectacular- already discussing another visit! Thank you!! Very clean, dock was great, nice breeze nightly. Central to everything.
    Reviewed 9 April 2018
    Beautiful views of Asseteague Island with lighthouse, ponies (with binoculars), fun dock to crab, kayak, or keep boat. Furniture and beds very comfortable and kitchen with...
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    About this property
    New Chincoteague rental with panoramic views of Asseteague Island, ponies and lighthouse. Enjoy sunsets, crab, fish, swim, and kayak from shared dock with optional boat slip. 2 bedrooms (full and 2 twin bunks) (queen) pullout queen couch in living room. One full bathroom. Newly renovated with new...
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    Chincoteague Island, Virginia
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Lighthouse Estates #31 / 22
    (2)Excellent
    0.4 kilometres from Proud Mary Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 September 2017
    The location was great, watching the lighthouse at night was amazing. The pool was wonderful to have and well cared for.
    Reviewed 29 June 2016
    Loved everything about this place! Location was perfect to Assateague Island and town. Our 13 year old twin grandchildren loved having big (queen-sizes) beds and own full...
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    About this property
    This comfortable, family friendly vacation rental is waiting for you to enjoy. This unit has pool access and dock access directly across the street for easy access for those fun family fishing and crabbing experiences. It is just a short distance to Memorial Park and Etta's Waterfront dining. The...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Wildflower1 / 34
    (1)Very good
    1.3 kilometres from Proud Mary Charters
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 May 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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Hill House1 / 18
    (2)Excellent
    1.2 kilometres from Proud Mary Charters
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 September 2013
    My family of five stayed with our in-laws with their family of six at this beautiful home in July of this year. Right on Main Street, within walking distance of a terrific...
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    About this property
    Welcome to the 'NEW' Hill House! Wonderful traditional island home with fantastic new upgrades! The kitchen has recently been renovated, along with the bathrooms. Excellent in town location, walk to dinner, movie, shopping & galleries. Hill House features 4 bedrooms and 2.5 bathrooms, with a first...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    Agape House1 / 15
    (1)Excellent
    1.2 kilometres from Proud Mary Charters
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 June 2016
    We have been vacationing on Chincoteague for years and Love everything about it, This is a great house with lots of room we had two adults and four teens and it worked out...
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    About this property
    A great three bedroom home with a convenient in town location - just a short distance to Maddox Blvd. and Main St. for dining, shopping, etc. The master suite has a queen bed and private bathroom with TV. The second bedroom offers two queen beds and lots of extra space. Through the open dining and...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sea Tag #221 / 19
    (1)Very good
    0.6 kilometres from Proud Mary Charters
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 August 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
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Sea Star1 / 17
    (2)Excellent
    1.0 kilometres from Proud Mary Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 July 2018
    This was our third time visiting Chincoteague, but our first time staying in the Sea Star rental. We chose Sea Star because it is pet friendly, and we wanted to bring our dog...
    Reviewed 30 May 2018
    We had a fantastic stay at sea star...the home was very clean and had everything we needed. Quiet street and close to everything. Short and convenient drive to state park...
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    About this property
    You cannot go wrong with this brand new beautiful vacation home!! Walking to restaurants, movies, shopping or anything else is just minutes away. Sea Star is a single story 3 bedroom 2 bathroom home that is tastefully furnished and decorated from top to bottom. The master suite boasts a queen bed...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Aerie (Sunset Bay 120)1 / 29
    (2)Very good
    1.3 kilometres from Proud Mary Charters
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Very roomy townhouse with beautiful views from the family room and two of the three bedrooms. Great location with walking distance to restaurants and some shops. Unfortunately...
    Reviewed 20 June 2018
    We stayed in #120 in Sunset Bay Villas. The condo was updated, beautifully decorated and clean. It was perfect for our family of 6. The location was great, right on the bay with...
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    About this property
    Come and enjoy this beautiful 3 bedroom villa! Conveniently located next to to pool, this ground-level condo allows you to walk right out from your balcony to the marina/dock. Enjoy all of the Chincoteague Island decor, spacious open floor plan, and the master bedroom suite featuring a private bath...
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    Location Information
    Chincoteague Island, Virginia
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Big Pines1 / 9
    (2)Excellent
    0.8 kilometres from Proud Mary Charters
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 November 2015
    Well maintained home within walking and biking distance of many shops and restaurants. Lovely screened in porch and the fire pit was an added bonus.
    Reviewed 26 September 2014
    I have went to chincoteague yearly since i was born and by far this is the first place i am going to stay for now on. Walking into this home i fell in love and instantly wanted...
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    About this property
    ***3545 Willow Street*** Very nice, comfortable 2 BR home will delight you with it's updated kitchen and new appliances. The large screened-in back porch with gas grill. Deck will accommodate outdoor entertaining. Centrally located, it is a short walk to town/shopping and the carnival grounds. 3...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    0.2 kilometres from Proud Mary Charters
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Tuck Inn1 / 4
    (2)Very good
    0.7 kilometres from Proud Mary Charters
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 August 2018
    Tuck Inn was great. It was our first time there. We have spent many summer weeks in Chincoteague and this place was the most "Chincoteaguey" of them all! Rustic and full...
    Reviewed 17 June 2016
    The house was nice but was older. It had the old beach house charm which we all loved. We had 3 kids with us (ages 3, 5, and 7). They all slept upstairs which was a little...
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    About this property
    ***6559 Church Street*** Island home with large back yard and deck and Internet. Pet Friendly! Nearby is Chincoteague Crossing. 2 bedrooms and 2 baths downstairs/2 bedrooms upstairs.*** Bed Sizes: 1 Queen, 1 Double, 4 Twin*** Prime Season Rates: $795 weekly/$159 per night. Off Season Rates:...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    0.4 kilometres from Proud Mary Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy this 2-bedroom, 2.5 bath townhouse in the Lighthouse Estates community off East Side Drive. There is a community pool as well as water access and a dock (shared) to fish and crab from. This unit features a washer/dryer, wireless internet, central air conditioning and all the other...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Lighthouse View Townhouse1 / 16
    (3)Very good
    0.4 kilometres from Proud Mary Charters
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 June 2018
    CRR has done it again. We have been vacationing in Chincoteague for the past 15 years. When our favorite Motel closed, CCR was able to help us find what we needed. This house...
    Reviewed 5 July 2016
    I enjoyed my stay in this home. My only complaint is that I initially inquired if there was a dishwasher prior to renting because it was not listed as an amenity. I was answered...
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    About this property
    Lighthouse View is located on the east side of our ialnd and includes a private community pool for your enjoyment. The 3 bedroom, 2 bath townhouse features two first floor bedrooms with full bath in the hallway and a master bedroom suite upstairs. There's water access across the street with a...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    0.8 kilometres from Proud Mary Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Wi-Fi
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This property has a location that is rich with amenities. Situated right next to Memorial Park, you can sit on the deck and enjoy the water views as the kids run, play, skateboard, fish and crab. The first floor is an open room consisting of the kitchen, dining area and living room (with queen...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cowboy Cottage1 / 18
    (4)Very good
    1.2 kilometres from Proud Mary Charters
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Wi-Fi
    • Grill
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 July 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 8 August 2017
    I found Chincoteague Island an enjoyable vacation destination. The Cowboy Cottage is a comforortable, somewhat rustic place to stay. It's central location on the island makes...
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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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ocean View Retreat1 / 25
    (5)Very good
    0.9 kilometres from Proud Mary Charters
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • DVD Player
    • Wi-Fi
    • Grill
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 May 2018
    Sleeps comfortably and privately for a large group; the kitchen & dining area are much too small, ie - one refrigerator in a 14 person house, multiple tables/rooms for eating...
    Reviewed 19 September 2015
    We rented this house because our favorite house with another Chincoeague rental agency was not available. While this house is nice, we prefer the other one. The view here is...
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    About this property
    Nestled on the eastern tip of Chincoteague Island, this spacious waterfront estate has been designed and meticulously constructed by a local craftsman. Enjoy the unobstructed views of Assateague Channel and the lighthouse while the sounds of nature delight your senses. Features include 5 bedrooms,...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    Charlotte's Morning Sun1 / 26
    (2)Average
    0.3 kilometres from Proud Mary Charters
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Waterfront
    • Balcony
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Paradise1 / 28
    (1)Excellent
    1.2 kilometres from Proud Mary Charters
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 August 2017
    Beautiful stunning and breath taking ! The view was beautiful. House was clean upon arrival, very spacious! Loved the kitchen. The bedrooms were very clean and spacious! Loved...
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    About this property
    If you're looking for that special vacation home that offers everything you'll need, look no further. Paradise offers all top-of-the-line amenities including cherry wood floors, chef's kitchen and spacious master bedroom suite with custom bathroom and Jacuzzi tub. The main floor features a bright,...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Mallard's Walk1 / 25
    (1)Excellent
    0.3 kilometres from Proud Mary Charters
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 August 2016
    This is the second year we stayed at Mallard's Walk. We have stayed different places over the years, and this is by far our favorite. We love that the dock is across the road...
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    About this property
    Enjoy the wonderful bay breezes from this charming waterfront home. Three bedrooms, great spacious kitchen, quiet porch to relax on and your own private pier/dock on Assateague Channel. Watch our world famous Chincoteague wild ponies grazing in the salt marshes of Assateague Island. No smoking and...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Assateague Light1 / 11
    (1)Very good
    0.4 kilometres from Proud Mary Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 August 2012
    Assateague Light is a very nice first-floor waterfront condo facing the Assateague Channel. The view from the deck is spectacular. When we were looking for vacation rentals on...
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    About this property
    This modern 2 bedroom condo located on the first floor features a master bedroom suite with a king bed, private bath and sliding glass door to the waterfront deck. The second bedroom has two twin beds with a full bathroom across the hall. This shared bath offers a walk in shower and washer/dryer....
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    Location Information
    Chincoteague Island, Virginia
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.4 kilometres from Proud Mary Charters
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tastefully remodeled beach home featuring a reverse floor plan and spectacular views of the Assateague Channel and Lighthouse! Located on the popular East Side of Chincoteague Island, Channel View is conveniently located near a public boat ramp, restaurants and Memorial Park. And you're about a...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1.1 kilometres from Proud Mary Charters
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Misty Sails1 / 13
    (1)Very good
    0.9 kilometres from Proud Mary Charters
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2018
    We enjoyed our stay at this house. The only reason I did not give a 5 star review was that we use the broiler a lot on vacation and the broiler was not working at the time of...
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    ***7136 Silver Sails Landing*** Spacious duplex overlooking the wetlands. With screen porch, deck, first floor master suite, enjoy the community pool after a long day at the beach! Next door to Bay Pony.*** Bed Sizes: 2 King, 2 Twin*** Prime Season Rates: $1350 weekly/$270 per night. Off Season...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Stingray1 / 15
    (2)Very good
    0.4 kilometres from Proud Mary Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed 1 September 2017
    I can not say enough about the view from this condo. The place was very clean and close to the beach and all of the attractions. The rental was clean and decorated nicely. My...
    Reviewed 9 July 2012
    I recently stayed at the stingray with my husband, our two-year-old son, and my mother who came for a few nights. The condo was well outfitted, comfortable and clean. It was...
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    About this property
    Luxurious 2nd-level waterfront condo with views you won't believe! Tastefully decorated with work of local artisans, features all amenities, as well as master bedroom suite with king bed & waterside balcony. Many extras like a flat screen TV and a Lazy Boy leather recliner. The open floor plan is...
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    Location Information
    Chincoteague Island, Virginia
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Island Thyme1 / 14
    (2)Very good
    0.9 kilometres from Proud Mary Charters
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Smoking allowed
    Reviewed 24 May 2017
    I found the house pleasant and pretty, the decor was all seaside with shells and beach shoes and quiet colours. I was disappointed that there was no wifi, as I had thought I...
    Reviewed 17 July 2013
    I loved this property. This was the third time my family and I stayed at Island Thyme. The location is great, it's in the middle of the little town and less than half a mile...
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    About this property
    There's plenty of room for everyone here at Island Thyme! This spacious home features a living room and den, large eat-in kitchen and dining area, and a huge wrap-around deck -- perfect for enjoying the quiet, peaceful setting. The many extras include a hot tub (on back deck), and Foosball table....
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    0.6 kilometres from Proud Mary Charters
    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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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.3 kilometres from Proud Mary Charters
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your home away from home... enjoy the water views, bring your boat and use your own dock or just relax and listen to the whispering pines. Great views of Oyster Bay off the front deck. 3 Bedrooms, 2 full baths (plus another shower/bath downstairs), outside shower, washer and dryer, satellite TV,...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    1.0 kilometres from Proud Mary Charters
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
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    ***3757 Willow Street*** Completely renovated traditional home in town with bright cheerful rooms and offers all amenities. Pet friendly! Two bedrooms on second level of home and two walk thru third story bedrooms. Third story loft with 4 twin beds has a typical Traditional home steep staircase....
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Panorama1 / 21
    (1)Excellent
    0.4 kilometres from Proud Mary Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    Reviewed 9 April 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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    Location Information
    Chincoteague Island, Virginia
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1.0 kilometres from Proud Mary Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
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    ***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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.8 kilometres from Proud Mary Charters
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    Smoking allowed
    About this property
    Cute as a button! This cozy little cottage sleep 5, and it's conveniently located very close to Memorial Park and Pony Swim area. If you're looking for an affordable vacation, this is it! The modern amenities make for an enjoyable vacation - there's central air, washer/dryer and outside swing....
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
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    Morning Memories1 / 21
    (1)Excellent
    0.4 kilometres from Proud Mary Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 August 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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.7 kilometres from Proud Mary Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Kid friendly
    Smoking allowed
    About this property
    Tastefully remodeled and decorated, 'Gone Coastal' is the perfect motto for this beach getaway! Located close to downtown - movies, shopping, restaurants and more. And you're only about 2 miles to the entrance to the beach! This rental features all modern amenities (central a/c & all appliances)...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Horseshoe Haven1 / 14
    (1)Very good
    0.2 kilometres from Proud Mary Charters
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 August 2018
    Cannot say enough about this wonderful rental & Harbour Realty. House was very clean & well stocked. A great family rental and a plus was being able to bring out pup...
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    ***7111 Horseshoe Lane*** Lovely home centrally located on a quiet residential street. Watch the Saltwater Cowboy's saddle up for the pony round ups right from the comfort of the airy screened porch. Too hot at the beach, no problem than enjoy the pool. This home has all the amenities for beach...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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    On Island Time1 / 20
    (1)Excellent
    1.2 kilometres from Proud Mary Charters
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 March 2017
    We have been coming to Chincoteague Island since 1988 and this is the best house we have been to. The décor is sweet and thoughtful. All the little touches are lovely and the...
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    About this property
    Wow... What a show piece! 'On Island Time' is exactly what you expect in your beach home, from the bright and fun decor to the spacious and bright floor plans, all of this wrapped in a traditional Eastern Shore Home. The front enclosed porch is great for reading or just relaxing in the afternoon...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    0.4 kilometres from Proud Mary Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • 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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Poppy's House1 / 9
    (1)Excellent
    1.1 kilometres from Proud Mary Charters
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Reviewed 23 July 2017
    This was the 4th time been to Poppy's House in Chincoteague.we stayed 10 days this time and loved every minute of it. The house had a great part in helping to make this vacation...
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    ***6313 Cleveland Street*** Walk to everything including shopping, restaurants and entertainment from this convenient in town location! This house has been completely renovated and is a great house for your vacation! Wireless internet!*** Outside Shower is not enclosed*** Bed Sizes: 2 Queen, 2...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sundance1 / 20
    (3)Excellent
    0.2 kilometres from Proud Mary Charters
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 September 2017
    Our stay was AMAZING!! Our family of 7 loved everything about this rental! Clean house, more than enough room for all of us, 3 full bathrooms! Quiet, welcoming home! We...
    Reviewed 2 August 2017
    This house is spacious, comfortable, well decorated, and labeled. Yes, labeled! The owner has every switch, cupboard, drawer, and remote labeled, which we really appreciated, as...
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    About this property
    Light, bright and airy - this beautiful home is very well maintained, tastefully furnished and boasts all amenities including screened porch, outside shower, all appliances including washer/dryer, tvs in every bedroom and more. The home is located just outside of town and offers a very quiet...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    A Second Wind1 / 21
    (1)Excellent
    1.2 kilometres from Proud Mary Charters
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Unfortunately we had to evacuate within 2.5 days of getting into the house. The house was absolutely beautiful with a great view. So far out of the 6yrs of coming I love the...
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    About this property
    A luxury waterfront vacation rental home with community pool privileges. Located on Chincoteague Bay, right at the water's edge. Enjoy breathtaking views and beautiful sunsets! On the first floor you'll find a sitting area (Double-size pull out sofa), two bedrooms (Queen & 2 Twins) with a common...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Serendipity1 / 20
    (2)Very good
    1.2 kilometres from Proud Mary Charters
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
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    Kid friendly
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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
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Blue Point1 / 19
    (3)Very good
    1.3 kilometres from Proud Mary Charters
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 October 2016
    My husband and I had the opportunity to stay at this home for a few days to attend the oyster festival. It is a very sweet and well maintained older home on a quiet lane. The...
    Reviewed 15 August 2014
    Cozy, old and comfortable shore farmhouse. It's near the fairground, and Pony Penning, as well as Rocket launch ....but all home. Best.
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    About this property
    Come for an old fashioned family vacation. This wonderfully maintained classic Chincoteague style home features a large screened porch and beautiful yard for those warm summer evenings and a wonderful enclosed outside shower. There is a family room with a wood stove, living room/library with lots...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1.2 kilometres from Proud Mary Charters
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***6242 Church Street*** Proud 3 story Traditional home located at the edge of town is rich in detail and history of the island. Beautiful renovations make this home just right for the whole gang. Just a few steps and walk to shopping and waterfront downtown plaza. Spacious rooms and large...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    0.9 kilometres from Proud Mary Charters
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Terrace
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    Smoking allowed
    About this property
    ***6422 Church Street*** Enjoy all that downtown has to offer in this cozy island home within walking distance to shops and restaurants. There is plenty of privacy in this petite home! First floor bedroom features a table and Tv, great for hanging out playing games or watching movies while others...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    Black Skimmer1 / 22
    (5)Very good
    1.1 kilometres from Proud Mary Charters
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 May 2018
    Lots of room for nine of us. The pool house was perfect for a little away time. The dogs loved the fenced in yard .Very clean. Little problem with the cooling system, fixed in...
    Reviewed 29 November 2017
    Easy rental process, great rates. House was very well equipped. Could have been a little cleaner when we arrived.
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    About this property
    Not your typical vacation rental home, Black Skimmer is a great rental that includes a separate guest house with game room. It boasts water views of Assateague Island! The main house has been tastefully restored and features hardwood floors and spacious rooms. There are bedrooms on both levels...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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