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Vacation Rentals near Captain Timothy Hill House

5122 Main St, Chincoteague Island, Virginia 23336-3103
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    Travelers to Chincoteague Island are booking September dates now. Secure your vacation rental today, and have the perfect trip.
    All 100 Rentals in Chincoteague Island
    Vacation House1 / 12
    (22)Excellent
    0.3 miles from Captain Timothy Hill House
    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
    0.5 miles from Captain Timothy Hill House
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Waterfront, 5 BR, 4 BA, Elevator, sleeps 101 / 48
    (1)Excellent
    0.8 miles from Captain Timothy Hill House
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Sweet Retreat:  Charming Cottage-Great for Family or Romantic Getaway1 / 28
    (3)Excellent
    0.4 miles from Captain Timothy Hill House
    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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    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    A Getaway1 / 20
    (3)Excellent
    0.1 miles from Captain Timothy Hill House
    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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    Chincoteague Island, Virginia
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Red Cedar1 / 27
    (3)Very good
    0.6 miles from Captain Timothy Hill House
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • DVD Player
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    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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    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    0.0 miles from Captain Timothy Hill House
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    • 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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cockleshell Cottage1 / 25
    (3)Excellent
    0.3 miles from Captain Timothy Hill House
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Windrush1 / 38
    (1)Excellent
    0.0 miles from Captain Timothy Hill House
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • DVD Player
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    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
    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
    1.2 miles from Captain Timothy Hill House
    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
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Epiphany on Deep Hole Creek - Waterfront & Dock -wow!1 / 31
    (44)Excellent
    0.7 miles from Captain Timothy Hill House
    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
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Saltings1 / 21
    (2)Excellent
    0.0 miles from Captain Timothy Hill House
    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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Water's Edge1 / 34
    (5)Average
    0.6 miles from Captain Timothy Hill House
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
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    • Waterfront
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Chincoteague Island, Virginia
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    June's Retreat1 / 37
    (1)Excellent
    0.4 miles from Captain Timothy Hill House
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Wi-Fi
    • DVD Player
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 17, 2016
    This is our 7th time vacationing in Chincoteague and June's Retreat was by far our favorite rental! We are a group of 12 and this spacious, beautifully decorated home easily...
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    About this property
    June’s Retreat is Chincoteague Island’s premier luxury vacation rental home, nestled on serene waterfront marshlands just north of town off of Main Street. This custom designed and decorated home leaves no detail unnoticed. From the bright spacious rooms with floor-to-ceiling windows to the...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    Joint Venture1 / 23
    (1)Excellent
    1.1 miles from Captain Timothy Hill House
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cowboy Cottage1 / 18
    (4)Very good
    1.2 miles from Captain Timothy Hill House
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lavinder House1 / 44
    (1)Excellent
    0.4 miles from Captain Timothy Hill House
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    0.7 miles from Captain Timothy Hill House
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    About this property
    Enjoy some of the island's best water views overlooking Oyster Bay from nearly every room of this custom beach home! Located on a bulk-headed waterfront lot in Richardson's Landing, you can fish and crab from the backyard! A wonderful feature of this spacious home is that you'll find your bedrooms...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Abbie Thornton Cottage1 / 22
    (1)Excellent
    0.0 miles from Captain Timothy Hill House
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 25, 2015
    My husband and I stayed at Abbie Thornton cottage in August 2015 and are SO happy we booked this place! It was absolutely wonderful, from the screened in porch (perfect spot...
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    About this property
    This charming Chincoteague cottage was built in the 1930's and is located directly across the street from the Chincoteague Bay. Abbie Thornton Cottage has kept much of the original integrity, but has been lovingly restored to offer all the modern comforts of home. There's a cozy screened porch off...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    A 'Teague of Our Own1 / 25
    (4)Excellent
    1.3 miles from Captain Timothy Hill House
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 days ago
    This home is great! Great location, plenty of space, nicely furnished and decorated! The yard is great if you have little kids as there is plenty of room for them to play, The...
    Reviewed August 17, 2018
    This pet-friendly home is a wonderfully comfortable place to spend a vacation. The owners have it furnished to satisfy many different tastes, - from those of us who like a...
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    About this property
    Welcome to A 'Teague of Our Own! Formerly known as 'Stormbreak,' this in-town home is an easy walk or bike to downtown or Maddox Blvd. Nicely decorated with three bedrooms. Living room has abundant seating a flat screen TV and DVD player. Wireless internet service is provided. The enclosed porch...
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    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    0.7 miles from Captain Timothy Hill House
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Catch of the Day is very comfortable and affordable duplex home that will cater to all of your vacation needs. This can be your home away from home - near the beach! The first level offers a large living room, a bedroom (D), an eat-in kitchen, 1/2 bath and very nice screened porch. There are two...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Snoozin' Goose1 / 28
    (3)Excellent
    0.6 miles from Captain Timothy Hill House
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
    Reviewed July 22, 2018
    We all loved it here - including our dog! Quiet location in Oyster Bay community which we love. Stayed here a few years back and it's even better now. Love the new paint and...
    Reviewed June 29, 2017
    Well appointed, nicely decorated and comfortable in a neat neighborhood. Three bedrooms and multiple porches for breezy comfort with views of the bay and it's dog friendly...
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    About this property
    Beautiful 3 bedroom home located in one of Chincoteague Island's private WATERFRONT communities! Snoozin' Goose offers multiple outdoor porches, an open floor plan with large, bright rooms and modern amenities -- all in a quiet, peaceful location. Enjoy wonderful water views while sitting directly...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sunset Bay Villa 3121 / 22
    (3)Very good
    0.6 miles from Captain Timothy Hill House
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 18, 2017
    We stayed at the Sunset Bay at two of the condo's managed by Chincoteague Resort Vacations and we were very happy with our stay. They were very responsive to a stubborn door...
    Reviewed August 3, 2014
    This was a wonderful place to stay. The pictures don't do this place justice. Definitely will stay again.
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    About this property
    Villa 312 is a beautiful 3 bedroom villa featuring a master bedroom suite with luxury bath, gourmet kitchen with center island which is great for entertaining, laundry room with washer/dryer and a waterside balcony overlooking Chincoteague Bay. There are tvs in all the bedrooms, and a computer desk...
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    Location Information
    Chincoteague Island, Virginia
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Osprey1 / 20
    (1)Excellent
    0.3 miles from Captain Timothy Hill House
    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 May 12, 2018
    Beautiful home great setup all you could ask for. Temperatures dropped and the winds were unbelievably cold during our stay. Pipes froze and we knew by the for sat that it...
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    About this property
    This great contemporary beach home is located at the edge of the community harbor area, a perfect location for you and your guests. As a pet friendly house, you'll enjoy the wide open spaces for your dogs. The home features an open floor plan with a lovely eat-in (and completely renovated!) kitchen...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Captain's Loft1 / 21
    (4)Very good
    0.9 miles from Captain Timothy Hill House
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 10, 2018
    Me and family really enjoyed our stay in this beautiful home in Chincoteague, very comfortable beds and rooms for a family of 8. the house is in a very quite location but near...
    Reviewed September 15, 2017
    Been coming to Chincoteague for years and have stayed all over the island. Hands down this is my favorite place. Clean, plenty of Bedrooms and Bathrooms. It also does have a...
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    About this property
    Captain's Loft has NEW OWNERS! This vacation home is located just a short walk to Maddox Blvd! Close to everything, but situated perfectly for a quiet and relaxing stay. This duplex home features three bedrooms downstairs, and two of those bedrooms have full baths. There's another full bath...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    0.7 miles from Captain Timothy Hill House
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Nestled on the edge of Assateague Bay and overlooking the wild salt marshes of Assateague and Morris Islands is where you'll find this gem. With capacity for 10 guests, the 4 bedroom 3 bath contemporary ranch home features a pier and dock on deep water, screened porch and open deck area, a widow's...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    0.4 miles from Captain Timothy Hill House
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Smoking allowed
    About this property
    A destination unto itself, Sea Oats offers wide open spaces, beautiful waterfront and views of Oyster Bay and plenty of room to spread out and relax. A luxury vacation rental home with all the bells and whistles, Sea Oats will delight your senses. From the tastefully decorated rooms and...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Castlebar1 / 49
    (1)Excellent
    0.8 miles from Captain Timothy Hill House
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 2, 2018
    Our family loves this open, bright house nestled in the beautiful marshes off Chincoteauge Bay. Waking up in the morning to the various wading birds and the sunset off the dock...
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    About this property
    Luxury waterfront home in Salt Marsh Landing. Spectacular sunsets. A long, private pier over the salt marsh leads you to a bay front dock area with shade. It's perfect for crabbing, fishing or canoe and kayak launching. Well appointed and architecturally pleasing, Castlebar features a main level...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    An Unfettered View1 / 25
    (5)Excellent
    0.9 miles from Captain Timothy Hill House
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    Reviewed May 26, 2017
    We try to visit the Eastern Shore near Assateague once a year in May before the summer crowds come in. We'd usually tent camp at Assateague seashore or Toms Cove but this year...
    Reviewed September 12, 2016
    This place is absolutely EVERYTHING you could hope for on vacation. The home is immaculately clean and lots of room. The well-kept , private dock is an exciting and successful...
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    About this property
    This beautiful 2 bedroom ranch home has a quiet, out-of-the-way location situated on little Oyster Bay. The views of the bay are beautiful and expansive with a long pier straight from the back deck. Its perfect for crabbing, kayaking & canoeing! An Unfettered View features all amenities including a...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Homestead1 / 37
    (2)Excellent
    0.0 miles from Captain Timothy Hill House
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 31, 2018
    We had another amazing stay on Chincoteague this year and love Homestead so much that it's the second year in a row we've booked it. It's cozy, quiet, has everything you need...
    Reviewed August 15, 2016
    We just spent a week at the Homestead, and it was everything we were looking for and more. We had a few semi rainy days and very high temps the whole time there. We all were...
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    About this property
    Set back across the street from Chincoteague Bay, Homestead sits on 5 acres and is a cozy 1890 cottage with the charm of yesterday and the comfort of today. Private, quiet, lots of room outside; it’s perfect for a retreat or family fun. Homestead sleeps 5 but is best suited for no more than 4...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    0.4 miles from Captain Timothy Hill House
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Coastal Breeze is a modern 3 bedroom, 2 bathroom single-family home located just off of North Main Street. You know as soon as you walk into this house that you are at the beach. There are tiled floors throughout the entire house with the exception of carpet in the bedrooms. The first floor offers...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Chincoteague Charm1 / 29
    (3)Average
    0.3 miles from Captain Timothy Hill House
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 10, 2015
    This was a wonderful beach house for our extended family vacation. Our four sons, their significant others and our two grandsons were able to sleep comfortably, eat meals all...
    Reviewed July 8, 2015
    We rented Chincoteague Charm and its guest cottage from June 28th- July 5th 2015. We have been traveling to the Island for the last 6 years during this time frame and it is a...
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    About this property
    Chincoteague Charm is a beautiful home located on North Main Street. It's just across the street from Chincoteague Bay and there is water access to the bay for kayaks & canoes. The home is very tastefully furnished, has a great kitchen/dining area with center island and quality stainless steel...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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    0.5 miles from Captain Timothy Hill House
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    All fresh, brand new, and waiting for you! The owners have taken great pleasure and pride in making this fabulous beach home everything that it is today. Enjoy the open floor plan inside that offers water views from nearly every room. There's also a dock with floating pier - perfect for launching...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Donovan's Reef1 / 15
    (1)Excellent
    1.1 miles from Captain Timothy Hill House
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    Reviewed August 11, 2014
    Just returned from one of the best vacations ever. This house was nice and big. There were 8 in our party and there was plenty of room to speed out. The kitchen was well...
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    About this property
    What a great house and it is PET FRIENDLY! Donovan's Reef is a classic home that offers large living spaces and bedrooms. On the first floor the original wood floors will guide you through a beautiful dining room (will seat 8 comfortably), right into a well appointed living room and den plus...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    0.3 miles from Captain Timothy Hill House
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Avalon is an exquisite 4 bedroom, 2.5 bathroom home situated on a bulkheaded lot on Oyster Bay! There is a large great room that boasts to family rooms, a dining area and large kitchen. Starting from the gas fireplace to the 16' cathedral knotted pine ceilings this home is bright, warm and...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Hidden Treasure1 / 32
    (1)Excellent
    0.9 miles from Captain Timothy Hill House
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 25, 2016
    We stayed here a few weeks ago. We had stayed in another house on the same street in a previous year- have been coming to the island for decades! The AC is COLD, the deck...
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    About this property
    Escape to the beach - come to this wonderful home nestled within one of Chincoteague Island's most prestigious communities. Hidden Treasure features a great open floor plan downstairs, as well as the privacy of a separate den (with sleep sofa), full bathroom and bedroom (2 twins). A full wall of...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    0.0 miles from Captain Timothy Hill House
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Poole's Cove manages to be tucked away right on Main Street. This home has been decorated with an artists' eye and poet's heart. The set up of this home offers plenty of room for the whole family, but enough distance for quiet moments to yourself. The Master bedroom suite is located in the main...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Admiral Benbow1 / 10
    (1)Excellent
    0.5 miles from Captain Timothy Hill House
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 30, 2013
    My favorite vacation home ever! This house was beautiful and you get that "beach feeling" as soon as you pull in. The bay is within view from the house and the beach is...
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    About this property
    A very nice contemporary home located in Oyster Bay I. Located next to the community boat ramp - you have access to the water and the kids can fish and crab from the dock areas. This house has an outdoor ramp to the ground level. Don't miss out on the great screened porch for a family dinner. Bed...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    0.4 miles from Captain Timothy Hill House
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Balcony
    • Terrace
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bay Dreamer is a spacious 3 bedroom duplex home with multiple porches and decks and spectacular sunset views, just minutes from downtown. When you enter the home you'll find a furnished rec room. The second floor features an open living room, dining area and kitchen. There is a large screened porch...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Heron's Cove On Salt Meadow1 / 21
    (1)Excellent
    1.0 miles from Captain Timothy Hill House
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Peaceful and stunning waterfront home! Located on a quiet side-street, Heron's Cove features a reverse floor plan with all bedrooms on the first floor, and the main living-level on the second floor. This allows you to capture and maximize the fabulous bay views! The second floor also features a...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Island Girl1 / 20
    (5)Very good
    0.7 miles from Captain Timothy Hill House
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Reviewed October 17, 2017
    First of all Island Girl has an Island vibe. The house is very bright and airy and it gets a lot of natural light. We enjoyed the deck and the screened in porch. It was misty...
    Reviewed September 17, 2015
    This was the perfect rental for our party. We had three couples and 4 kids. There are three beds, all queen, and the loft has four twins. The kids loved being in the loft...
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    About this property
    Spacious waterfront home with water views from every window! The Great Room includes comfortable living and dining areas and a modern, fully stocked kitchen w/ breakfast bar. Amenities include central heat & air, private outside shower, wood stove, grill, screened porch and lots of deck space! And...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    1.1 miles from Captain Timothy Hill House
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Air Conditioning
    • Housekeeping Included
    • DVD Player
    • Washer
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    SEA HARBOR: 1 mile from Assateague Island and 5 miles from beach front fun. Check-In 4pm Check-Out 12pm. This home offers large open spaces, a cozy, clean and comfortable place to stay along with amazing adventures for everyone to explore. It is furnished with many necessities so you can rest,...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    0.6 miles from Captain Timothy Hill House
    6 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy bay views and stunning sunsets from rocking chairs on the front porch and serene views over a tidal creek while dining on the back porch. This 3,000-square-foot, three-story home in the quiet, wooded neighborhood of Smuggler’s Cove is surrounded by loblolly pines and shares a boat launching...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 6 Bedrooms, 2 Bathrooms, Sleeps 8
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    1.1 miles from Captain Timothy Hill House
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Check out one of Chincoteague Island's newest vacation rental listings! You'll be delighted by the fresh, clean spaces and modern amenities. Natural pine wood adorns the trim, floors and vaulted ceilings allowing for an open, spacious feel. MAIN HOUSE ('Coastal Escape'): Downstairs features the...
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    Location Information
    Greenbackville, Virginia
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Southern Dream1 / 22
    (1)Excellent
    0.8 miles from Captain Timothy Hill House
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 12, 2016
    My family has stayed at this rental for the last few summers when we go to Chincoteague. My favorite thing here is the view of the water from the deck. We love cooking out...
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    About this property
    Charming 3 bedroom ranch home located in one of Chincoteague Island's finer residential communities. Nice, quiet location with a water view of Oyster Bay. Spend your time outside on the spacious deck or screened porch - there's plenty of room for all! Many modern amenities such as central air, high...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    0.4 miles from Captain Timothy Hill House
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spectacular waterfront home on the end of a cul-de-sac! Bright, airy and immaculate! Four decks, (one off of the stunning 2nd floor - Private Master Suite). Dramatic cathedral ceiling in the cozy, waterfront living room. A screened porch to host an outdoor dinner. Central heat, a fireplace (pellet...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    1.3 miles from Captain Timothy Hill House
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We're pleased to be able to offer 'Pelican's Roost' as one of the newest additions to our fine selection of vacation rentals! As the middle unit in a triplex, Pelican's Roost offers fabulous water views and expansive porch and deck areas. You'll enjoy the bright and spacious open floor plan...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    0.6 miles from Captain Timothy Hill House
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful bay-front home overlooking Oyster Bay - a kayakers' paradise. Your group of 8 will enjoy the peace & quiet this home has to offer. There's a dock with floating boat launch for easy in/easy out. As you enter this home, on the main level you'll find a great open floor plan with stunning...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Windshadow1 / 27
    (1)Excellent
    0.4 miles from Captain Timothy Hill House
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Wi-Fi
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 10, 2018
    Great location, close to town. Beautiful view of the Chincoteague Bay. Lovely, well-organized home. Pet friendly, took our 2 dogs. We have stayed at several homes in...
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    About this property
    You will enjoy spectacular sunsets from this lovely waterfront home overlooking the Chincoteague Bay. There is a waterfront screened gazebo that leads to a dock great for crabbing/fishing. Inside is a large open floor plan with a brand new kitchen, living room with wood burning fireplace and dining...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    0.1 miles from Captain Timothy Hill House
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A true architectural delight, 'Cozy View' is one of Chincoteague Island's unique gems. Conveniently located on North Main Street, this cottage is close enough to town, yet just far enough away to offer some peace and quiet. The stunning water views of the Chincoteague Bay and million-dollar sunsets...
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    Location Information
    Greenbackville, Virginia
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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