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Holiday Rentals near Captain Timothy Hill House

5122 Main St, Chincoteague Island, Virginia 23336-3103
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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
    Spend Christmas by the Sea at Jay's Retreat; Rates Starting at $49/Ngt; Pets Ok1 / 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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    Vacation House1 / 12
    (20)Excellent
    0.3 miles from Captain Timothy Hill House
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    1.1 miles from Captain Timothy Hill House
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • 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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    0.4 miles from Captain Timothy Hill House
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Patio
    • Private Garden
    • Wi-Fi
    • DVD Player
    • Grill
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spend Christmas by the Sea: Holly Day Market, Tree Lighting, Christmas Parade, Children's Christmas Tea, Progressive Home Tour, New Year's Eve Concert, Polar Plunge, Pony Island Horseshoe Drop Check out our October & November Specials. Rates as low as $60/Night...
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    Chincoteague Island, Virginia
    Holiday Rental House - 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 19 June 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 19 May 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
    Holiday Rental House - 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
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 June 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 30 September 2016
    My wife and I stayed here in early September, 2016 for four nights to go kayaking and explore the area. The house worked very well for us. The beauty of the Red Cedar is the...
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    About this property
    Nature calls at this nicely appointed 3 bedroom rental home! Red Cedar is nestled on the edge of a huge expanse of nature preserve-type land where you'll see all types of native wildlife. Birders bring your life list. The home features modern amenities, offers a first floor bedroom, full laundry,...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Agape House1 / 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
    • Wi-Fi
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 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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    0.0 miles from Captain Timothy Hill House
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Grey Heron is an amazing contemporary waterfront home nestled on the shoreline of Chincoteague Bay. You'll love the floor plan; a terrific great room with wood floors flanked by a kitchen on one side and a fireplace on the other. And great windows throughout! There's also a 'sitting room' with...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 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
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 June 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 24 May 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
    Holiday Rental House - 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
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 May 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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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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 12 June 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 31 August 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
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    1.1 miles from Captain Timothy Hill House
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Balcony
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***6402 Teal Lane*** The unobstructed view of Eel Creek and Little Oyster Bay will get your attention at sunrise and sunset! Put your kayak in the water at the shared dock at high tide. Now has WiFi and 42' TV*** This Property accepts Weekly Rentals Only.*** Bed Sizes: 2 Queen, 1 Bunk Bed...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 July 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 21 April 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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    1.1 miles from Captain Timothy Hill House
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Balcony
    • Air Conditioning
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***6204 Poplar Street*** Island Cottage has a great in town location! Easy walk to historic downtown's shops and retaurants. Perfect for a budget frienldy vacation. Has Wi-Fi.*** This Property accepts Dogs 35lbs and Under Only.*** Bed Sizes: 1 Queen, 1 Double, 1 Twin.*** 2018 Off Season...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Water's Edge1 / 34
    (4)Very good
    0.6 miles from Captain Timothy Hill House
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • DVD Player
    • Washer
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 May 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 17 October 2016
    This recently renovated home features an open floor plan with wrap around windows facing out to the water. The small watch tower at the top of the house has stunning views and...
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    About this property
    Water's Edge is an adorable Bay Front cottage in walking distance to Chincoteague's Historic Downtown. You'll be impressed by the charm of this home from the time you pull in the driveway. On the first floor you'll find a full bathroom with an open great room with expansive bay views. There is a...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 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 17 July 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
    Holiday Rental House - 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
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 June 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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.9 miles from Captain Timothy Hill House
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Grill
    • Terrace
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***4473 Deep Hole Road*** This wonderful duplex has all the amenities you'd want including LOCATION!! Just off Maddox Blvd., you have easy access and can walk to everything! ***Electric Grill*** Bed Sizes: 1 Queen, 1 Twin Daybed w/Trundle, 1 Queen Sleep Sofa*** Prime Season Rates: $795...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1.0 miles from Captain Timothy Hill House
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***4312 Main Street*** Enjoy the water view from this immaculate home offering spacious rooms and a quiet location off Main Street. All bedroom on the same level.*** Bed Sizes: 3 Queen, 1 Double Futon*** Prime Season Rates: $775 weekly/$155 per night. Off Season Rates: $600 weekly/$120 per...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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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 16 November 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
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Key West Cottages1 / 4
    (13)Excellent
    1.1 miles from Captain Timothy Hill House
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Patio
    • Balcony
    • Hot Tub
    • Air Conditioning
    • Parking
    • Shared Indoor Pool
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    My husband and I had a great weekend on Chincoteague Island and absolutely LOVED the lavender cottage we stayed in. The view was breathtaking and the cottage was welcoming and...
    Reviewed 2 weeks ago
    the oyster cottage has a gorgeous view, wrap around porch and the interior is cozy and charming , offering everything you need to make it a perfect stay.The staff at the Comfort...
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    About this property
    Beautiful cottages located in the heart of Downtown Chincoteague with views of the Chincoteague Channel and Bay. The Key West Cottages are equipped with full kitchens, cozy living rooms, Queen bedrooms and large tiled showers. Amenities such as an indoor pool, hot tub and outdoor pool next door...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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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
    Kid friendly
    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
    Holiday Rental House - 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 25 August 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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    0.7 miles from Captain Timothy Hill House
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
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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
    Holiday Rental House - 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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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 July 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 29 June 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
    Holiday Rental House - 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
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 July 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 3 August 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 12 May 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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Captain's Loft1 / 22
    (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 10 October 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 15 September 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
    Holiday Rental House - 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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    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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    0.7 miles from Captain Timothy Hill House
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Located very close to town, Bay Breeze will remind you of summer vacations as a child. This 3 bedroom, 2 bath homes sleeps 6 and has a washer & dryer, window a/c, and a ton of charm! Comfortable and affordable - this may be your spot at the beach! Additional amenities include: 2 twins bedding 2, 2...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.4 miles from Captain Timothy Hill House
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Half Shell1 / 8
    (2)Excellent
    0.3 miles from Captain Timothy Hill House
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***5277 Oyster Court- Oyster Bay I*** Oyster Bay I home will delight you with it's spacious bedrooms and lovely back sunroom. Small screen porch in front and a fish cleaning table belo, the home is set-up to enjoy. Offers wireless internet and satelite tv.*** Bed Sizes: 2 Queen, 2 Twin, and 1...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    1.1 miles from Captain Timothy Hill House
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
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    ***6248 Ocean Boulevard*** Walk to restaurants, shopping, etc. from this in town home. Nearby is Atlantic Delight and A Sea Change. WiFi Available. Upstairs offers a master suite with a private bathroom and 2 bedrooms and a full bath. 1/2 bath downstairs.*** Bed Sizes: 1 Queen, 4 Twin*** Prime...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Castlebar1 / 46
    (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 2 July 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
    Holiday Rental House - 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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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 May 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 13 September 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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    0.3 miles from Captain Timothy Hill House
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
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    ***5323 Hibiscus Drive-Oyster Bay I*** This spacious pet friendly home is located in the private community of Oyster Bay II. Enjoy your morning coffee from the large deck or screened porch. Wildlife abounds with deer, rabbits, ducks, geese, and lots of songbirds in this quiet retreat! Enjoy...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Shady Rest1 / 10
    (1)Excellent
    1.0 miles from Captain Timothy Hill House
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 August 2018
    This was an absolute hidden gem! Kitchen was newly remodeled and well stocked. Made breakfast every morning and 2 dinners during our stay. Everything we needed was there. I...
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    ***6303 Chester Park***** Well appointed home located in quiet neighborhood offers first floor bedroom and bath. Offers internet access!*** Bed Sizes: 2 Queen, 2 Sets of Bunks(1 Twin & 1 Double on each)*** Prime Season Rate: $975 weekly/$195 nightly. Off Season Rates: $625 weekly/$125 nightly....
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Homestead1 / 13
    (2)Excellent
    0.0 miles from Captain Timothy Hill House
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 July 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 15 August 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
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, 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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    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    East Wing1 / 11
    (2)Very good
    0.7 miles from Captain Timothy Hill House
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Terrace
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    Pet friendly
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    Smoking allowed
    Reviewed 24 June 2018
    Absolutely amazing loved this place, cute comfortable family home. Minutes from everything. Would stay here again. Also recommend to anybody. You will be very pleased
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    About this property
    ***5159 Deep Hole Road*** This charming island cottage built in 1920 features wood plank floors, open-beam ceilings, a screened-in porch and a large yard. Llovingly restored, East Wing is within walking distance of Little Oyster Bay, a boat launch, playground, restaurants and the best ice cream...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    0.9 miles from Captain Timothy Hill House
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    ***6301 Circle Drive*** Charming pet friendly cottage in serene island setting with easy access to the Beach and to the Old Town. Spacious yard and screened porch. 2 full bathrooms. Bedrooms include 1 large master BR with king-size; plus 1 BR with 2 twins; and a cozy den with sofa/sleeper. Pet...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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 10 August 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 8 July 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
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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    0.7 miles from Captain Timothy Hill House
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***5082 Twilley Drive*** Contemporary 4 bedroom 3 bath Waterfront home. Pet friendly, located in a private area off North Main Street. Offers 2 master suites with waterfront balconies. This home does not disappoint with its vaulted ceilings and gas fireplace. Offers a well-equipped kitchen with...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    Smoking allowed
    About this property
    All fresh, brand new, and waiting for you! You won't believe the NEW Nautilus! The new 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...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.6 miles from Captain Timothy Hill House
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***5392 Sunrise Drive-Oyster Bay I*** Newly remodeled in 2014 now with an open floor plan and expanded rooms! The renovated kitchen in this Oyster Bay waterfront home will inspire cooks and the new dining room is terrific for family gatherings. There is lots of new decking and when you're not at...
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    Location Information
    Chincoteague Island, Virginia
    Holiday Rental House - 4 Bedrooms, 3 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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    Smoking allowed
    Reviewed 11 August 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
    Holiday Rental House - 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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    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
    Holiday Rental House - 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 25 July 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
    Holiday Rental House - 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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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