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Holiday Rentals in Chilmark

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    Travellers to Chilmark are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    All 27 Rentals in Chilmark
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    Charming Chilmark 3 Bedroom 3 Bath Vacation Home1 / 10
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    CHILMARK - Deer Run-French Country Style Farmhouse w/ Hot Tub1 / 50
    (4)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Private Garden
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    Pet friendly
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    Smoking allowed
    About this property
    Lovely rural home near farms, yoga studio. Across from preservation land with hiking trail. Walk to Grange Hall, Farmer's Market, general store and cafe. ( 2000 ft² ) New master suite in pleasant cottage style home. Grassy yard and small garage. Isolated setting but convenient. Close to desirable...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Reverse Contemporary Five Bedroom home just minutes to Menemsha. There are open living spaces with living room , dining room and kitchen that open to deck with waterviews of the North Shore. Just a short drive to famous Lucy Vincent Beach, Chilmark Store, library and Community Center. Walk to a...
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    Chilmark, Martha's Vineyard
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 9
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    4 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
    About this property
    This spacious, comfortably furnished home is conveniently located between Chilmark and West Tisbury. The master bedroom and a bath are downstairs; three bedrooms and a bath are upstairs off the loft that overlooks the living and dining rooms. The living and dining rooms have a cathedral ceiling,...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Air Conditioning
    • Balcony
    • Terrace
    • Patio
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming 5 bedroom, 4 bath home located at Prospect Hill in Chilmark has a great layout and excellent location. Main level has generous kitchen, open living dining area, and master bedroom and bath, all light and bright with extensive decking and French doors to connect the interior to the...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    CLASSIC VINEYARD FISHING VILLAGE VIEWS FROM THIS QUINTESSENTIAL COTTAGE1 / 12
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Satellite TV
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    About this property
    What a location! Located in Menemsha with classic Vineyard fishing village views this cottage is the quintessential vacation home. You can walk to the beach to picnic, fish or watch beautiful sunsets and you can also walk to one of the Island's most popular seafood restaurants. It is light, airy...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    ATLANTIC OCEAN BREEZES, GLORIOUS VIEWS!1 / 22
    (1)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
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    • Grill
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 June 2014
    We stayed at this gorgeous home with a large family group in March. Fortunately for us, the weather was ideal. We had a lovely stay - everything at the house was wonderful and...
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    About this property
    A boutique hotel experience in an unrivaled setting at the end of a one mile single lane road. Enjoy the sunrise from the ocean, sunset over the adjoining 13 acre Sheriff's Meadow Foundation conservation preserve. This home has a wonderful view toward Squibnocket Beach, a mile away, and the...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Internet Access
    • Washer
    • Parking
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Island Romance is a Chilmark vacation rental with ocean views on a quiet plot of land, featuring a shared dock, spacious yard, and studio cottage. Bring your friends and loved ones to this sweet New England farmhouse on Martha's Vineyard. In summer you'll be able to use the home's semi-private dock...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Set on 5 acres of woods and meadow. A small farm setting with chickens and pigs and a garden for you to enjoy. Be a farmer for a week, without the work! Our hens lay eggs that you can collect every morning. The pigs love your dinner scraps and we invite you feed them if you wish. The animals are...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    Pet friendly
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    Smoking allowed
    About this property
    C-H-A-R-M-I-N-G is the only word to describe this privately set little contemporary with a big heart, tucked right into the woods in Spring Point. Lovely view of the Sound over the tree tops from the full length inside comfort of screened-in porch. Convenient kitchen opens into living and dining...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Washer
    • Grill
    • Parking
    • Porch
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located at end of a dead-end dirt road on 1.5 acres with tall pines and oaks. Modified saltbox, owner designed & built in 1978 for potential active solar. First floor has a large country kitchen, living room, bathroom with antique claw foot bathtub & w/d, & 2 decks. Second floor has 2 bedrooms with...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Grill
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A perfect vacation house with miles of hiking trails and the best vineyard beach at your doorstep. Enjoy the "play" pool which is 4 feet deep and nice to relax in on a beautiful sunny vineyard day. Built with water therapy and children in mind; handicapped accessible. Total privacy, in one of the...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Parking
    • Internet Access
    • DVD Player
    • Grill
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With old-world charm aplenty and modern amenities, you'll enjoy a relaxing holiday at this Chilmark vacation rental. It's a great spot for a family looking for a quiet refuge. You're near the center of town and close to iconic businesses, but you're also not far from the cliffs at Aquina as well as...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Satellite TV
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful, custom 4-bedroom house in an exclusive neighborhood with private association beach and tennis court. Spacious, comfortable living and dining room with cathedral ceilings, open to kitchen and upstairs loft with office. TV/sitting room nook off dining room. Expansive deck with stunning...
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    Chilmark, Martha's Vineyard 02539
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    6 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Grill
    • Satellite TV
    • Hot Tub
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious, 10 room, architectual award-winning design home perched atop a hill w/panoramic view of Vineyard Sound and the Elizabeth Islands. The large deck has marvelous water views and the sunsets are spectacular! Its charming interior includes a Living Room with vaulted ceilings,fireplace and...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
    • Washer
    • Parking
    • Outdoor Dining Area
    • Grill
    • Central Heating
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy the secluded beauty of this award-winning, architect-designed home in Chimark on almost four acres of land. Relax on the two level deck or on the beach at Lucy Vincent, Squibnocket, or nearby Menemsha. The remarkable design makes great use of over 3500-square-foot space by joining the...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Satellite TV
    • Patio
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Historic 18th century New England home in a private landscaped setting on two and 1/2 acres with a waterview over Vineyard Sound and the Elizabeth Islands; a detached two-car garage, bunkhouse; tennis court and in-ground heated lap pool located on Menemsha Inn Road in the Town of Chilmark. The...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Central Heating
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Clean and family friendly. Centrally located, the cottage is only fifteen minutes from most island towns including Edgartown and Aquinnah, where dining and shopping are world renowned. Lovely wooded setting offers privacy with large comfortable deck and yard. Outdoor shower adds to the Vineyard...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
    • DVD Player
    • Patio
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unique combination of 1940's camp-style home and new (2007) two-story addition. Beautiful Ocean views from all floors, two decks, two living rooms and wonderful prevailing SW breezes. Five minute walk to Ocean Beach adjacent to Lucy Vincent Beach. Access to private Able's Hill Association beach and...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Grill
    • Wi-Fi
    • Ocean Views
    • DVD Player
    • Air Conditioning
    • Balcony
    • Washer
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enter our vacation world up a 0.2 mile paved driveway through the woods to the private hilltop with only two other houses. Open the gate and delight at the expanse of ocean view from the deck over oak trees - our 3 1/2 acres adjacent to a sanctuary seem like 100. Listen to the birds and the surf...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 9
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    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Grill
    • DVD Player
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great location. Menemsha Village. 2 bedroom cottage. Sunny interior. 1 bath, plus outdoor shower. Storage barn, cable tv, High Speed internet, washer. Walk to beach, harbor, dock, stores, restaurants. Currently available August only. $1595 per week. 2 wk minimum. Maximum occupancy 2 adults,...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tastefully furnished and decorated with antiques and art. This upscale Chilmark summer home is an original Yankee Barn located off South Road that has all the accouterments for summer entertaining. The post and beam structure features a beautiful cathedral living room brightened by southern light;...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Simply charming home that enjoys one of the most breathtaking views you will ever see. Perched high on a hill, the views of Menemsha Pond, Vineyard Sound, the Elizabeth Islands beyond and the nearby marshlands with their abundant bird life are simply mesmerizing.The newly-refreshed home has open...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    • Air Conditioning
    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in a tranquil setting overlooking Chilmark Pond off of South Road this is a magical summer vacation spot. Additional amenities include: coffee maker, outdoor shower, lobster pot, food processor, cd player, wine glasses, washer & dryer, ironing board.
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • DVD Player
    • Grill
    • Satellite TV
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Vacation in Chilmark near the pristine shores of the Tisbury Great Pond in this brand new, custom contemporary built with only the best materials. Four-bedroom main house with a detached guest suite. Open living / dining/ kitchen area with cathedral ceilings and exposed beams overlooking a...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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