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Holiday Rentals and Villas in Chilmark, MA

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    All 176 Rentals in Chilmark
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    Travellers to Chilmark are booking August dates now. Secure your holiday rental today, and have the perfect trip.
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    £221
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    1 / 10
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    £160
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    1 / 22
    5 Bedrooms / 2 Bathrooms / Sleeps 9
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    £577
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    5 Bedrooms / 4 Bathrooms / Sleeps 12
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    £2,403
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    1 / 20
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Smoking allowed
    • Elder access
    • ?
    • ?
    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... View all property information
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    Chilmark, Martha's Vineyard 02535
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    £1,022
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    1 / 12
    2 Bedrooms / 1 Bathroom / Sleeps 3
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    • Air Conditioning
    • Washer
    • Grill
    • Refrigerator
    • Stereo System
    • DVD Player
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    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,... View all property information
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    Chilmark, Martha's Vineyard 02535
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    £3,300
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    1 / 14
    1 Bedroom / 2 Bathrooms / Sleeps 3
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • DVD Player
    • Satellite TV
    • Waterfront
    • Deck
    • Grill
    • Water Views
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    'The Little House' on the beach. Two minute stroll to South surf beach. Incredible views from sunrise to sunset. Private tennis courts shared with owners and other tenants. Access to Stonewall Pond for launching canoes and kayaks. This wonderful cottage is a one of a kind. A pet will be considered... View all property information
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    Chilmark, Martha's Vineyard
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    £1,602
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    1 / 23
    5 of 5 stars (1) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Grill
    • Deck
    • Internet Access
    • Stereo System
    • DVD Player
    • TV
    • Dryer
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Unique waterfront living in the heart of Chilmark. The Boathouse sits directly on the shores of Stonewall Pond, with sweeping water views of the Pond, Stonewall Beach and the Atlantic Ocean. You also have access to Stonewall Beach -- one of Chilmark's most prestigious private association beaches.... View all property information
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    Chilmark, Martha's Vineyard
    5 of 5 stars Reviewed 27 December 2013
    we have stayed in this property 3 years running in both June and July. It's the most peaceful spot imaginable (no mobile phone signal) with unending wildlife activity ( we have...
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    £1,602
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    1 / 36
    4 Bedrooms / 5 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Internet Access
    • Dryer
    • Stereo System
    • Deck
    • Washer
    • TV
    • DVD Player
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Featuring one of the most stunning water views and waterfront locations in Chilmark, The Beach House At Stonewall is just that. Stonewall Beach is directly at the property's edge. There is a private beach, and south-facing views of Stonewall Beach & Pond, Squibnocket Point, and on out to No Man's... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    £3,204
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    1 / 17
    3 Bedrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Deck
    • Dishwasher
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Microwave
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Stunning Chilmark property in Abel's Hill. Convenient location with great proximity to association beach and tennis, not far from Chilmark and West Tisbury town centers. Surrounded by open rolling hills with Japanese garden and fire pit, offering great privacy. Just steps to wonderful walking... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    £366
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    1 / 5
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Fireplace
    • Wi-Fi
    • Air Conditioning
    • Linens Provided
    • Satellite TV
    • Deck
    • Private Outdoor...
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    A perfect vacation house with miles of hiking trails and the best vineyard beach at your doorstep. Relax in the pool ~ it's heated! The 'play' pool is 4 feet deep. Built with water therapy and children in mind; handicapped accessible. Total privacy, in one of the nicest parts of the island. The... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
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    From
    £504
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    1 / 8
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Water Views
    • Wi-Fi
    • Stereo System
    • Deck
    • Satellite TV
    • DVD Player
    • Patio
    • Boat Available
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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... View all property information
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    Chilmark, Martha's Vineyard 02535
    From
    £2,563
    / Week
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    1 / 22
    5 of 5 stars (1) Excellent
    4 Bedrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Waterfront
    • Internet Access
    • Stereo System
    • Water Views
    • Satellite TV
    • Fireplace
    • Air Conditioning
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Chilmark waterfront rental home located on Quitsa Pond with views across Quitsa and Menemsha ponds out to the Elizabeth Islands. This martha's vineyard rental property offers dock, mooring along with access to small beach area just down the path on Clam Point Cove. Named appropriately, it is an... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    5 of 5 stars Reviewed 3 September 2014
    Our family thoroughly enjoyed our week at the Mayhew home in Chilmark. We rented kayaks for some boating right off the private pier, picked clams, swam off the docked and cooked...
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    £2,659
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    1 / 10
    4 of 5 stars (1) Very good
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Internet Access
    • Stereo System
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Deck
    • Dishwasher
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Owner Transfer Ferry Tickets - Please Inquire Situated on a cul-de-sac overlooking a private meadow with spreading oaks ensures privacy. The screened porch, meadow bench, hammock and second floor deck off the master bedroom provide quiet spots to get away. Amenities and Features include...... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    4 of 5 stars Reviewed 11 August 2014
    Great vacation. Home was clean, property is private and quiet and as always, very comfortable. Convenient location for our family vacation needs. Lack of recycling at house...
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    From
    £3,076
    / Week
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    1 / 21
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Dryer
    • Washer
    • Satellite TV
    • Deck
    • DVD Player
    • Stereo System
    • Grill
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This house is set in a pastoral surrounding. It has beautifully tended grounds with a Peter Rabbit enclosed flower garden and rolling lawns. The well equipped gourmet kitchen overlooks the dining and living rooms. There is a four season porch off the living room and a sun bathed deck. The... View all property information
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    Chilmark, Martha's Vineyard
    From
    £1,282
    / Week
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    1 / 17
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    Overview Make Enquiry
    Amenities & Details
    • Stereo System
    • Air Conditioning
    • Dryer
    • Internet Access
    • Satellite TV
    • DVD Player
    • Washer
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Charming cottage with water view just steps into Menemsha. Great outdoor deck, new kitchen - everything recently updated. Wonderful antiques for decoration and top quality furnishings throughout. Additional amenities include: coffee maker, smoke free, 6 dining capacity, pets considered, lobster... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    £1,922
    / Week
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    1 / 13
    3 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Satellite TV
    • Deck
    • Washer
    • Grill
    • Internet Access
    • DVD Player
    • Dryer
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Newly renovated kitchen. Great yard and deck. Tucked into the woods off South Road. 1.3 miles from West Tisbury town center. Access to Lucy Vincent and Squibnocket Beaches. Convenient location in Chilmark. West Tisbury Farmer's Market & Artisan's Market are just down the road. Relax in the privacy... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    £1,922
    / Week
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    1 / 23
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Washer
    • Stereo System
    • Dryer
    • Deck
    • Patio
    • TV
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Pine Ridge Farm sits peacefully tucked away on three acres of gently rolling meadows surrounded by stone walls. At the center of the compound is a classic Royal Barry Wills cape that has been smartly designed and finely appointed. An open Great Room with Living and Dining Areas has a two-story... View all property information
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    Chilmark, Martha's Vineyard
    From
    £1,922
    / Week
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    1 / 26
    5 Bedrooms / 3 Bathrooms / Sleeps 9
    Overview Make Enquiry
    Amenities & Details
    • Washer
    • Patio
    • DVD Player
    • Deck
    • Dryer
    • TV
    • Stereo System
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    The ultimate artist or family retreat tucked away amid the rolling hills and stonewalls of Squibnocket Pond in Chilmark. The panoramic water views look out across the Pond, the barrier beach and sand dunes of the Island's southwestern most point, and on out to No Man's Island and the Atlantic... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    £1,922
    / Week
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    1 / 24
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • TV
    • Internet Access
    • Deck
    • Washer
    • Dryer
    • Patio
    • Stereo System
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Enjoy sweeping water views across Stonewall Pond and Beach, as well as access to the private ocean beach at prestigious Stonewall Beach. Lenom House is tucked away between Stonewall and Quitsa Ponds, with dramatic water views of both well known Chilmark Ponds, plus the south shore and Stonewall... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    £1,121
    / Week
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    1 / 8
    2 Bedrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Fireplace
    • Satellite TV
    • Internet Access
    • Stereo System
    • Deck
    • Grill
    • Dishwasher
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    A perfect up-island retreat - this charming two bedroom cottage has all that you could possibly imagine, nicely updated and comfort throughout. Enjoy Chilmark's famous beaches by day, relax on the screened porch with a book before dinner -- this is the meaning of rest and relaxation! Additional... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    £1,282
    / Week
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    1 / 19
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Washer
    • Dryer
    • Stereo System
    • DVD Player
    • TV
    • Patio
    • Internet Access
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Quietly tucked away in a pastoral setting on Blueberry Ridge, Meadow House features a modern interpretation of a sleek barn. The home is designed to enjoy the views of the surrounding secluded meadows both inside and out. The main living space features an open design floorplan with Living and... View all property information
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    Chilmark, Martha's Vineyard
    From
    £8,010
    / Week
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    1 / 40
    5 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • DVD Player
    • Stereo System
    • Internet Access
    • TV
    • Deck
    • Washer
    • Patio
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Aptly named for its stunning perch in prestigious Squibnocket Farm on the shores of Squibnocket Pond, The Roost features panoramic water views that stretch from the far southwestern shoreline of Martha's Vineyard, across Chilmark's Squibnocket and Stonewall Beaches, and continue along the Island's... View all property information
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    Chilmark, Martha's Vineyard
    From
    £1,922
    / Week
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    1 / 21
    5 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • TV
    • Deck
    • Stereo System
    • Dryer
    • Patio
    • DVD Player
    • Washer
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Privately tucked away on 20 acres of rolling hills and meadows that run along the shoreline of Squibnocket Pond, this mission-style home enjoys stunning sunset and water views across the Pond, the sand dunes of the Island's most southwestern point, and on across the Atlantic Ocean out to No Man's... View all property information
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    Chilmark, Martha's Vineyard
    From
    £2,884
    / Week
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    1 / 22
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Internet Access
    • Stereo System
    • Grill
    • Washer
    • DVD Player
    • Deck
    • Dryer
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Sitting high atop a ridge in Chilmark, the distant ocean views from Hilltop House stretch as far as Woods Hole and the Elizabeth Islands to Menemsha. The three-acre hillside setting is both spectacular and private. The recently renovated house has two walls of glass sliding doors that frame the... View all property information
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    Chilmark, Martha's Vineyard
    From
    £6,600
    / Week
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    1 / 35
    5 Bedrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Water Views
    • DVD Player
    • Internet Access
    • Fireplace
    • Deck
    • Stereo System
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Through the private gate this home is set up on the hill with stunning views of Squibnocket Pond and the South Shore of the Atlantic. With endless windows to capture the natural surroundings and decks to enjoy the sun. 5 bedrooms and 5 baths allow the entire family their own space. An open kitchen... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    £2,243
    / Week
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    1 / 35
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Internet Access
    • Washer
    • Grill
    • TV
    • Dryer
    • Deck
    • Dishwasher
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Hill House sits atop a bluff along the shores of Stonewall Pond with panoramic water views of the Pond and Stonewall Beach, as well as views over Quitsa Pond in the other direction. There is also access to Stonewall Beach, one of Chilmark's most prestigious private association beaches. Hill House... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    £1,282
    / Week
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    1 / 23
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • DVD Player
    • Patio
    • TV
    • Stereo System
    • Washer
    • Dryer
    • Internet Access
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Luxurious beachfront living in Chilmark with sweeping water views of Stonewall Beach, Squibnocket Ridge, and Stonewall Pond. The Pond House sits directly on the intersection of Stonewall Beach and Pond, with water views throughout the house and across the large wraparound deck. Walls of windows and... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    £1,602
    / Week
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    1 / 21
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Washer
    • Internet Access
    • Deck
    • Dryer
    • TV
    • DVD Player
    • Stereo System
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Privately tucked away in the rolling hills of the historic Tea Lane area, surrounded by conservation land, the newly renovated Chilmark Retreat features a sleek modern style, with a sunny, open floor plan. There are sharp designer touches throughout, mixed with monochromatic shades of white and... View all property information
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    Chilmark, Martha's Vineyard
    From
    £12,816
    / Week
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    1 / 28
    6 Bedrooms / 6 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • Patio
    • Grill
    • DVD Player
    • Washer
    • TV
    • Stereo System
    • Internet Access
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Vista Point combines a truly magical mix of a spectacular, waterfront location, with equaling stunning architectural design. Sitting high atop a north shore ridge in Chilmark, the views stretch west from the Aquinnah cliffs and lighthouse, north to the Elizabeth Islands, and east toward Lambert's... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    £5,126
    / Week
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    1 / 26
    4 Bedrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Deck
    • Internet Access
    • Satellite TV
    • Dishwasher
    • Fireplace
    • Water Views
    • Stereo System
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Spectacular waterviews! This Martha's Vineyard vacation rental is situated on 3+ acres overlooking the Elizabeth Islands and the Vineyard sound. On a clear day you can catch a lovely view of the Aquinnah lighthouse. The outdoor living space is truly where you want to be. Each area used for various... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    £2,243
    / Week
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    1 / 25
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • DVD Player
    • TV
    • Stereo System
    • Dryer
    • Internet Access
    • Washer
    • Patio
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    A quiet oasis tucked away on Blueberry Ridge, the Hillside Hideaway enjoys a tranquil country setting with rolling meadows, and thoughtfully designed outdoor landscaping with patios and outdoor living spaces set amid nicely manicured grounds and gardens. Inside, the house is designed to enjoy the... View all property information
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    Chilmark, Martha's Vineyard
    From
    £8,010
    / Week
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    1 / 31
    7 Bedrooms / 4 Bathrooms / Sleeps 9
    Overview Make Enquiry
    Amenities & Details
    • Dryer
    • Stereo System
    • DVD Player
    • Patio
    • Washer
    • Internet Access
    • Grill
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Serenely tucked away on the rolling hills and meadows of prestigious Seven Gates Farm, this Classic Chilmark home sits directly on the north shore with stunning water views of Vineyard Sound and the Elizabeth Islands, with its own curving coastline of Seven Gates beach. There is vintage charm... View all property information
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    Chilmark, Martha's Vineyard
    From
    £8,010
    / Week
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    1 / 29
    5 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Deck
    • DVD Player
    • Dryer
    • Stereo System
    • Patio
    • Washer
    • Internet Access
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Tucked away in the prestigious Quansoo area of Chilmark, this architect-designed compound sits peacefully on the shores of the Tisbury Great Pond. There are sophisticated touches inside and out, with a Main House, Guest House, and key access to Quansoo Beach. The Main House is centered around a... View all property information
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    Chilmark, Martha's Vineyard
    From
    £4,934
    / Week
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    1 / 23
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Patio
    • TV
    • Dryer
    • Grill
    • DVD Player
    • Internet Access
    • Stereo System
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    This historic farmhouse is quietly tucked away above Menemsha Pond with sweeping sunset and water views of The Pond and Menemsha Harbor. The tranquil setting is classic Chilmark with rolling hills and stonewalls, plus a private association beach just a short stroll away on Menemsha Pond.... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    £3,204
    / Week
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    1 / 21
    3 Bedrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Deck
    • DVD Player
    • Grill
    • Fireplace
    • Stereo System
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Chilmark waterview vacation rental. Driving down the wooded, rural road to this property you will see the grounds and water views open up to you as you approach. Wonderful yard with lots of space for afternoon picnics, lounging on the patio and cocktails in the evening after a great day on the... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    £92
    / Night
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    1 / 9
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Wi-Fi
    • Water Views
    • Satellite TV
    • DVD Player
    • Boat Available
    • Waterfront
    • Deck
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    The Pond House, located on Stonewall beach in Chilmark, is a charming cottage is situated on the edge of the rolling lawns of the main house. The beauty and serenity experienced here are what the Vineyard is all about; Stonewall Pond to the west, the Atlantic to the southeast. The house has two... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    £201
    / Night
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    1 / 18
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • DVD Player
    • Refrigerator
    • Internet Access
    • Linens Provided
    • Deck
    • Satellite TV
    • Stereo System
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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;... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    £183
    / Night
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    1 / 8
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Grill
    • Dishwasher
    • Water Views
    • Stereo System
    • Porch
    • Internet Access
    • Satellite TV
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    £229
    / Night
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    1 / 21
    5 of 5 stars (1) Excellent
    4 Bedrooms / 5 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Satellite TV
    • Deck
    • DVD Player
    • Fireplace
    • Wi-Fi
    • Water Views
    • Waterfront
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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... View all property information
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    Chilmark, Martha's Vineyard 02535
    5 of 5 stars Reviewed 17 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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    From
    £8,010
    / Week
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    1 / 26
    7 Bedrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Fireplace
    • Water Views
    • DVD Player
    • Stereo System
    • Internet Access
    • Deck
    • Waterfront
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    SPECTACULAR and expansive views of the Vineyard Sound with 2-miles of private association beach to meander anytime your heart desires, lots of exploring or jumping from the infamous rock into the ocean below for the more adventuresome, all with Seven Gates tennis courts, trails and 2 Docks at your... View all property information
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    Chilmark, Martha's Vineyard 02535
    From
    £286
    / Night
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    1 / 13
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Fireplace
    • Satellite TV
    • Deck
    • Hot Tub
    • Water Views
    • DVD Player
    • Wi-Fi
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Welcome to Menemsha! This 3 bedroom home is located on a 2.3 acre wooded lot in a very quiet setting with superb water views toward the Elizabeth Islands. The private yard has a wooden deck for outdoor grilling and dining. The interior is comfortable and clean. The first floor Master bedroom has a... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02552
    5 of 5 stars Reviewed 1 July 2013
    If I could take this house and bring it home I would!! What a charming cottage all decorated in a nautical theme just as I expected. The cleanest place I"ve stayed so far. Loved...
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    From
    £549
    / Night
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    1 / 20
    6 Bedrooms / 4 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • Water Views
    • Private Outdoor...
    • Fireplace
    • Satellite TV
    • Wi-Fi
    • Patio
    • Stereo System
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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... View all property information
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    Chilmark, Martha's Vineyard 02535
    From
    £96
    / Night
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    1 / 11
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Refrigerator
    • Stereo System
    • Grill
    • DVD Player
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This spacious and comfortably furnished contemporary Cape is conveniently located between Chilmark and West Tisbury. The master bedroom and 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... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    £440
    / Night
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    1 / 16
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Waterfront
    • Satellite TV
    • DVD Player
    • Patio
    • Water Views
    • Wi-Fi
    • Fireplace
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Beautifully restored, maintained, and furnished, this 1740 Island farmhouse is situated on 80 private acres of glorious Chilmark hills overlooking Menemsha Pond and includes a small private association beach on Menemsha Pond to wend your way down to. A little bit of heaven on earth! Additional... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02539
    From
    £1,282
    / Week
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    1 / 13
    4 Bedrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Grill
    • Satellite TV
    • Microwave
    • Deck
    • Stereo System
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    A very special Windy Gates offering. Four bedroom converted barn offers a large open first floor with kitchen, dining and living space. Great barn doors open to patio seating outside. Four bedrooms upstairs with one hall bath and a second bath at the bottom of the stairs. Enjoy this Martha's... View all property information
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    Chilmark, Martha's Vineyard
    From
    £92
    / Night
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    1 / 12
    4 of 5 stars (1) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Refrigerator
    • Porch
    • Microwave
    • Water Views
    • Satellite TV
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02552
    From
    £870
    / Night
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    1 / 15
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Water Views
    • Satellite TV
    • Deck
    • DVD Player
    • Grill
    • Wi-Fi
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02539
    From
    £9,932
    / Week
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    1 / 13
    5 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Water Views
    • Air Conditioning
    • Refrigerator
    • Grill
    • Stereo System
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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. View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    £10,253
    / Week
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    1 / 24
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Refrigerator
    • Private Outdoor...
    • Stereo System
    • Satellite TV
    • Fireplace
    • Hot Tub
    • Linens Provided
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    A complete complex in a beautiful, peaceful setting: main house and barn with built-in pool, hot tub, private tennis court and pond. One can walk to a lovely North Shore beach. This complex is surrounded by roses and perennials. Also, beach stickers for Lucy Vincent and Squibnocket are provided.... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    £6,408
    / Week
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    1 / 19
    4 Bedrooms / Sleeps 9
    Overview Make Enquiry
    Amenities & Details
    • Water Views
    • Stereo System
    • DVD Player
    • Fireplace
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Stunning Chilmark property with wonderful privacy, peace and tranquility. This Martha's Vineyard vacation rental offers access to two keyed private association beaches Squibnocket Association and Long Beach, distant peak of a view to the Atlantic Ocean with classic Chilmark living and access to... View all property information
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    Location Information
    Chilmark, Martha's Vineyard