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Holiday Rentals and Villas in Chilmark, MA

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    All 86 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.
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    From
    £219
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    1 / 10
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    £159
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    1 / 22
    5 Bedrooms / 2 Bathrooms / Sleeps 9
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    £572
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    5 Bedrooms / 4 Bathrooms / Sleeps 12
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    £2,383
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    1 / 20
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • 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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    £1,013
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    1 / 12
    2 Bedrooms / 1 Bathroom / Sleeps 3
    Overview Make Enquiry
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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
    From
    £3,272
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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
    From
    £363
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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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    Chilmark, Martha's Vineyard 02535
    From
    £499
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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
    £2,033
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    1 / 17
    3 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Fireplace
    • Internet Access
    • Washer
    • Deck
    • Grill
    • Satellite TV
    • DVD Player
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Rustic colorful camp with a gorgeous water view right on Chilmark Pond. Sleeps six. Simple kitchen with all necessities. Wow your guests with gourmet meals from this quaint kitchen. Comfortable living-dining overlooking the pond. A special get-away like old times. Not many of these left! Row or... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    £1,906
    / 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
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    From
    £436
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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
    £862
    / 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
    £200
    / 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
    £182
    / 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
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    1 / 4
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Dryer
    • Stereo System
    • Fireplace
    • Washer
    • Deck
    • DVD Player
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Secluded location on a cul de sac overlooking a private meadow with spreading oak trees. The traditional exterior welcomes you to our spacious contemporary. the main living area features a great room with fireplace which opens to a dining room and kitchen with an island eating bar. Off the great... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    £545
    / 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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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    £91
    / 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
    £283
    / 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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    £91
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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
    £2,224
    / Week
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    1 / 11
    5 Bedrooms / 3 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • Satellite TV
    • Grill
    • Deck
    • Internet Access
    • DVD Player
    • Ceiling Fans
    • Dishwasher
    • Microwave
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Spacious, well furnished and equipped, comfortable home in quiet neighborhood on 3 acres. Two master bedrooms, one on each floor; pool table. Within walking distance (about 1 mile) to small North Shore beach (Great Rock Bite). Three mile drive to Lucy Vincent Beach. Amenities and Features... View all property information
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    Chilmark, Martha's Vineyard
    From
    £227
    / 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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    Location Information
    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
    £681
    / Night
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    1 / 17
    6 Bedrooms / 6 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Fireplace
    • Water Views
    • DVD Player
    • Deck
    • Internet Access
    • Satellite TV
    • Hot Tub
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    £10,166
    / 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
    £95
    / 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
    £4,003
    / Week
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    1 / 29
    4 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Water Views
    • Stereo System
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Patio
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This incredible home is furnished with one of a kind artisan wood and textile pieces, as well as Donghia soft seating and is filled with art, vintage stain glass, antiques, and one of kind artisan furniture. The ocean view is spectacular from the great room (living room, dining area and kitchen,... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    £9,849
    / 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
    £8,896
    / Week
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    1 / 13
    5 Bedrooms / 6 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Wi-Fi
    • Water Views
    • Satellite TV
    • Air Conditioning
    • Waterfront
    • Boat Available
    • Deck
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    £454
    / Night
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    1 / 18
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Internet Access
    • Water Views
    • Satellite TV
    • Private Outdoor...
    • Fireplace
    • DVD Player
    • Deck
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    A fascinating, lovely classic Eliot Noyes (architect) contemporary in a private setting with spectacular views off the water looking toward Lucy Vincent beach and East towards West Tisbury. There is a great room (with dining, and living room and kitchen) with decks on either side (4-10 feet off the... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    £7,942
    / Week
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    1 / 16
    5 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Stereo System
    • Internet Access
    • Deck
    • Air Conditioning
    • Washer
    • Satellite TV
    • DVD Player
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Newly constructed home has open concept living area with 270 degree water views, abundant natural sunlight, central AC, high end appliances, hardwood floors, rooftop deck with seating to view gorgeous island sunsets, access to several private beaches,and high speed internet wifi. Additional... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    £1,684
    / Week
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    1 / 11
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • DVD Player
    • Dishwasher
    • Ceiling Fans
    • Deck
    • Satellite TV
    • Internet Access
    • Grill
    • Microwave
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Lovely 3 bedroom 2 bath home. All new kitchen and baths. Completely renovated - lots of glass for a light filled interior. This lovely home in a private setting is surrounded by mature Holly trees, Laurel and attractive native shrubs. 1 mile to Alley's General Store. 10 minute drive to Lucy Vincent... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    £1,588
    / Week
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    1 / 12
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Internet Access
    • DVD Player
    • Stereo System
    • Dryer
    • Fireplace
    • Satellite TV
    • Deck
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This newly remodeled 3 bedroom 2 bath has a spacious master bedroom suite, cozy sun room and updated kitchen. It has a great yard with garden landscaping, a perfect spot for outdoor dining. 1.5 miles from Alley's store. 3.3 miles to Lucy Vincent Beach.The bathrooms are fully remodeled. An easy,... View all property information
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    Chilmark, Martha's Vineyard
    From
    £2,113
    / Week
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    6 Bedrooms / 2 Bathrooms / Sleeps 14
    Overview Make Enquiry
    Amenities & Details
    • Satellite TV
    • Washer
    • Grill
    • Deck
    • Internet Access
    • Stereo System
    • DVD Player
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    A large rambling old family home where memories are made. The extended family can all join in a vacation full of laughter and play. The grounds are full of places for hide-and-go-seek. Privately set on Middle Road in the woods yet bathed in sunlight. The house has a string of bedrooms for all the... View all property information
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    Chilmark, Martha's Vineyard
    From
    £4,765
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    1 / 23
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Stereo System
    • Washer
    • Fireplace
    • Satellite TV
    • Internet Access
    • Grill
    • Deck
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This Chilmark contemporary home offers views over Chilmark Pond to the South Shore. There are four bedrooms three full baths an open floor plan that includes a kitchen, living room and dining room that open up to decks and additional living space. Includes canoe to take over the pond to beautiful... View all property information
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    Chilmark, Martha's Vineyard
    From
    £1,588
    / Week
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    1 / 15
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Stereo System
    • Dryer
    • Washer
    • DVD Player
    • Dishwasher
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located on South Road near Able's Hill, this family oriented house comes with access to a private South Shore beach across Chilmark Pond. Have fun boating, kayaking or canoeing across the pond to the beach. A family room in the lower level provides space for the younger members of the family to... View all property information
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    Chilmark, Martha's Vineyard
    From
    £1,525
    / Week
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    1 / 24
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • Dishwasher
    • Satellite TV
    • Grill
    • Microwave
    • Water Views
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Pristine modern summer cottage with distant views of Lucy Vincent Beach, privately nestled on historic Eddy Farm, hillside, off of South Rd. This light filled home with acres of privacy is the perfect retreat for those looking for a long term summer stay in Chilmark with Lucy Vincent Beach just a... View all property information
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    Chilmark, Martha's Vineyard
    From
    £2,192
    / Week
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    1 / 15
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • DVD Player
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Perched high above the surrounding terrain, this affordable Chilmark rental offers sweeping views of the ocean and upisland all the way to Aquinnah. See the sunsets from the deck. It is spacious with 4 bedrooms to accommodate family and friends. See Chilmark rental #CH224 for family reunions or... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    £1,271
    / Week
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    1 / 22
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Deck
    • Washer
    • Stereo System
    • TV
    • Grill
    • DVD Player
    • Fireplace
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located on Flanders Lane, this house sits up the hill and looks toward Menemsha. It is private and protected by the trees. Walk to watch sunsets in Menemsha or dine in one of the places to eat there or take in a day at the beach. Additional amenities include: beach chairs, dock/boat-slip, coffee... View all property information
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    Chilmark, Martha's Vineyard
    From
    £3,050
    / Week
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    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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    Location Information
    Chilmark, Martha's Vineyard
    From
    £5,083
    / Week
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    1 / 24
    4 Bedrooms / 2 Bathrooms / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Satellite TV
    • Dryer
    • Deck
    • Fireplace
    • DVD Player
    • Washer
    • Stereo System
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located in Menemsha down a dirt road to privacy and serenity, this house is constructed carefully and artfully. The space is light filled with cathedral ceilings in the living area grounded by a hand built fireplace. All decorations and objects have been carefully picked to accent the space with... View all property information
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    Chilmark, Martha's Vineyard
    From
    £7,625
    / Week
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    1 / 32
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Deck
    • Private Outdoor...
    • Internet Access
    • Grill
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    7 acre Luxury Chilmark Estate in an Idyllic setting of stone walls, perennial gardens and orchards. Private pool and hot tub surrounded by a large deck and bordered by tiered rose gardens. A regulation tennis court is set a short walk across the meadow. There is a beautiful natural pond on the... View all property information
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    Chilmark, Martha's Vineyard
    From
    £5,401
    / Week
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    1 / 29
    6 Bedrooms / 2 Bathrooms / Sleeps 11
    Overview Make Enquiry
    Amenities & Details
    • Dryer
    • Fireplace
    • Washer
    • DVD Player
    • Satellite TV
    • Deck
    • Stereo System
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Style, warmth, and comfort define this delightful farm house in Menemsha with a water view to the Vineyard Sound. The property is spacious and private. There is a tennis court shared by the occupants of the neighboring barn. The house comes with a key to a beach in Aquinnah on Moshup trail and a... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    £1,716
    / Week
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    1 / 20
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Satellite TV
    • Washer
    • Internet Access
    • Deck
    • DVD Player
    • Grill
    • Stereo System
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This bright and cheerful, wooded retreat is truly tranquil, yet just a little over a mile from West Tisbury village, with its General Store (Alley's), Farmer's Market, Artisan's Festivals and Flea Market. This home has been recently updated by its new owners. They have chosen the loveliest colors... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    £2,542
    / Week
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    1 / 20
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • DVD Player
    • Internet Access
    • Stereo System
    • Fireplace
    • Dryer
    • Deck
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Fabulous Chilmark home offers two levels of living sapce. On the first floor there is a fully equipped kitchen open to the dining room, a living room with fireplace, built-ins and sliders to a deck overlooking a meadow and the most incredible water views. There is a half bath, a master suite with... View all property information
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    Chilmark, Martha's Vineyard
    From
    £2,033
    / Week
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    1 / 18
    5 Bedrooms / 2 Bathrooms / Sleeps 9
    Overview Make Enquiry
    Amenities & Details
    • Washer
    • Grill
    • Satellite TV
    • DVD Player
    • Stereo System
    • Dryer
    • Deck
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    £2,224
    / Week
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    1 / 23
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Stereo System
    • Internet Access
    • Water Views
    • DVD Player
    • Waterfront
    • Satellite TV
    • Grill
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Ocean Front Splendor in an elegant and comfortable beach house. Sunrise from the ocean, sunset over the adjoining 13-acre Sheriff's Meadow Foundation conservation preserve. Walk to the Stonewall Association private beach. Two master bedrooms, two twin-bed bedrooms. All four bedrooms have private... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    £5,083
    / Week
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    1 / 23
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Satellite TV
    • Stereo System
    • Dryer
    • Deck
    • Washer
    • Internet Access
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Panoramic Views of South Shore from across the Allen Farm to Noman's Land and beyond. This carefully designed and decorated home sets you in beauty and comfort. The deck features a gazebo. The yard is carefully landscaped and tended with trees strategically planted to offer privacy between the main... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    £1,398
    / Week
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    1 / 21
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Washer
    • Stereo System
    • Grill
    • Deck
    • Satellite TV
    • Internet Access
    • DVD Player
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This special summer retreat affords unforgettable views, a quiet and private setting, an awesome deck to sit and watch and let it all go. Newly renovated gourmet kitchen. The hgouse has views from every room. Watch the sailboat races on Menemsha Pond, the herons, the deer and the hawks on the... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    £3,971
    / Week
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    1 / 19
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Internet Access
    • Dishwasher
    • Washer
    • Dryer
    • Deck
    • Stereo System
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Sit on the porch of this fabulous four bedroom home and take in the panoramic water views. Enjoy watching the sheep grazing around the property which is part of a working farm. Access a gorgeous south shore private beach by canoe or kayak. The home is private, comfortable and convenient to the... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    £4,765
    / Week
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    1 / 17
    4 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Deck
    • Internet Access
    • Satellite TV
    • Stereo System
    • DVD Player
    • Washer
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This spacious ten room, architectural award winning design home is perched high on a hill with panoramic views of the Vineyard Sound and the Elizabeth Islands. There are five bedrooms, four and one half baths, a large deck for entertaining and watching the breathtaking sunsets, and three outdoor... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    £2,542
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    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Water Views
    • Satellite TV
    • Grill
    • Deck
    • DVD Player
    • Waterfront
    • Stereo System
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Main House on the same property may be occupied by Owner or another Tenant. Peaceful private setting on one of the most beautiful areas on the South Shore. Amenities and Features include... Waterfront Guest House, Private Beach Additional amenities include: coffee maker, internet - ethernet... View all property information
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    Location Information
    Chilmark, Martha's Vineyard