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Vacation Rentals in Chilmark, MA

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    $345
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    1 / 10
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    $250
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    5 Bedrooms / 2 Bathrooms / Sleeps 9
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    $900
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    5 Bedrooms / 4 Bathrooms / Sleeps 12
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    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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    $1,595
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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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    1 / 17
    3 Bedrooms / 2 Bathrooms / Sleeps 7
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    • 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
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    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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    Chilmark, Martha's Vineyard 02535
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    $571
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    1 / 5
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • 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
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    $857
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    1 / 20
    6 Bedrooms / 4 Bathrooms / Sleeps 12
    Overview Make Inquiry
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    • 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
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    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
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    $1,750
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    1 / 8
    2 Bedrooms / Sleeps 4
    Overview Make Inquiry
    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
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    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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    Chilmark, Martha's Vineyard 02535
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    $4,150
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    1 / 10
    4 of 5 stars (1) Very good
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Inquiry
    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
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    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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    Chilmark, Martha's Vineyard
    4 of 5 stars Reviewed August 11, 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
    $4,450
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    1 / 18
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Water Views
    • Grill
    • Satellite TV
    • DVD Player
    • Dishwasher
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Panoramic South Shore ocean vista from this outstanding private rental home. Less than one mile to famous Lucy Vincent Beach. Owner also offers private beach rights to the south side via canoe or kayak (provided by owners.) Classic style and modern luxury combine to make this family retreat a very... View all property information
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    Chilmark, Martha's Vineyard
    From
    $686
    / Night
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    1 / 16
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Inquiry
    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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    Chilmark, Martha's Vineyard 02539
    From
    $446
    / Night
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    1 / 13
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Inquiry
    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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    Chilmark, Martha's Vineyard 02552
    5 of 5 stars Reviewed July 1, 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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    $286
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    1 / 8
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Inquiry
    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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    Chilmark, Martha's Vineyard 02535
    From
    $4,000
    / Week
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    1 / 14
    5 Bedrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Microwave
    • Internet Access
    • Water Views
    • Deck
    • Satellite TV
    • Dishwasher
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Stunning Chilmark rental property with beautiful views to the south across Squibnocket Pond and the Atlantic and to the north across Menemsha Pond to the Elizabeth Islands. The house was built in the 1950s in a manner to maximize the enjoyment of the wonderful setting and views. It is surrounded by... View all property information
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    Chilmark, Martha's Vineyard
    From
    $143
    / Night
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    1 / 12
    4 of 5 stars (1) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Reviews (1) Make Inquiry
    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
    $357
    / Night
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    1 / 21
    5 of 5 stars (1) Excellent
    4 Bedrooms / 5 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Inquiry
    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 June 16, 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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    $143
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    1 / 9
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Inquiry
    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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    Chilmark, Martha's Vineyard 02535
    From
    $786
    / Night
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    1 / 8
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Inquiry
    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
    $5,000
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    1 / 17
    3 Bedrooms / Sleeps 6
    Overview Make Inquiry
    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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    Chilmark, Martha's Vineyard
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    From
    $150
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    1 / 11
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Inquiry
    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
    $1,071
    / Night
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    1 / 17
    6 Bedrooms / 6 Bathrooms / Sleeps 10
    Overview Make Inquiry
    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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    Chilmark, Martha's Vineyard 02535
    From
    $1,357
    / Night
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    1 / 15
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Inquiry
    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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    Chilmark, Martha's Vineyard 02539
    From
    $15,500
    / Week
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    1 / 13
    5 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Inquiry
    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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    Chilmark, Martha's Vineyard 02535
    From
    $2,500
    / Week
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    1 / 36
    4 Bedrooms / 5 Bathrooms / Sleeps 8
    Overview Make Inquiry
    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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    Chilmark, Martha's Vineyard
    From
    $16,000
    / Week
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    1 / 24
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    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
    $14,000
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    1 / 13
    5 Bedrooms / 6 Bathrooms / Sleeps 10
    Overview Make Inquiry
    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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    Chilmark, Martha's Vineyard 02535
    From
    $314
    / Night
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    1 / 18
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Inquiry
    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
    $714
    / Night
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    1 / 18
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Inquiry
    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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    Chilmark, Martha's Vineyard 02535
    From
    $3,000
    / Week
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    1 / 26
    5 Bedrooms / 3 Bathrooms / Sleeps 9
    Overview Make Inquiry
    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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    Chilmark, Martha's Vineyard
    From
    $2,500
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    1 / 23
    5 of 5 stars (1) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (1) Make Inquiry
    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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    Location Information
    Chilmark, Martha's Vineyard
    5 of 5 stars Reviewed December 27, 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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    From
    $3,175
    / Week
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    1 / 24
    4 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Waterfront
    • Microwave
    • DVD Player
    • Water Views
    • Deck
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Casual immaculately clean in picturesque Menemsha, Chilmark waterfront. Beautiful views. A short stroll to the beach, fish market, boutiques, fishing, and shore dinners. Guest House - Main House on property nearby may be occupied by Tenants or Owner. Amenities and Features include...... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    $6,150
    / Week
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    1 / 14
    4 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • DVD Player
    • Internet Access
    • Water Views
    • Satellite TV
    • Stereo System
    • Dishwasher
    • Deck
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Sweeping water view over Vineyard Sound to the Elizabeth Islands. Freshly renovated Cape-style, three bedrooms, with sofa beds in den and sunroom, sleeps 8-10 people. Short walk to lovely Menemsha Village, and less than two miles to Lucy Vincent's Beach. Large, landscaped treed lot of 2.3 acres on... View all property information
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    Chilmark, Martha's Vineyard
    From
    $4,000
    / Week
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    1 / 8
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Inquiry
    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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    Chilmark, Martha's Vineyard
    From
    $2,000
    / Week
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    1 / 23
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Inquiry
    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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    Chilmark, Martha's Vineyard
    From
    $5,150
    / Week
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    1 / 31
    5 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Deck
    • Water Views
    • Satellite TV
    • Porch
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    MVVR EXCLUSIVE: Spectacular 5 bedroom, 4.5 bath retreat. Lovely distant waterviews overlooking the South Shore. Hilltop setting with privacy and a five minute drive to Lucy Vincent Beach. This spacious custom home has been decorated by one of the island's premier professionals. A combination of... View all property information
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    Chilmark, Martha's Vineyard
    From
    $4,225
    / Week
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    1 / 26
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Dishwasher
    • DVD Player
    • Water Views
    • Internet Access
    • Deck
    • Satellite TV
    • Waterfront
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This quintessential Chilmark home has been impeccably maintained and continuously updated. The dining and living areas open to a wrap around deck. Enjoy spectacular water views and sunsets from just about every room in the house. Stroll to the beach and Menemsha village where you will find the fish... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    $1,950
    / Week
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    1 / 15
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Grill
    • Deck
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Satellite TV
    • Stereo System
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Amenities and Features include... North Slope Hilltop House. Private yard, Screeen Porch and Patio, All new AC Throughout, 8 minute drive to Lucy Vincent Beach or Menemsha Village Additional amenities include: coffee maker, patio table and chairs, fans - portable, lobster pot, washer / dryer, cd... View all property information
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    Chilmark, Martha's Vineyard
    From
    $4,500
    / Week
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    1 / 18
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Waterfront
    • Dishwasher
    • DVD Player
    • Water Views
    • Deck
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Amenities and Features include... Quansoo (with private beach key), Central Air, Waterview, Waterfront Additional amenities include: coffee maker, internet - ethernet cord required, pets considered, lobster pot, washer / dryer, cd player, porch - screened, outside shower - enclosed, private... View all property information
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    Chilmark, Martha's Vineyard
    From
    $2,500
    / Week
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    1 / 21
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Inquiry
    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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    Location Information
    Chilmark, Martha's Vineyard
    From
    $3,800
    / Week
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    1 / 24
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • DVD Player
    • Grill
    • Internet Access
    • Satellite TV
    • Waterfront
    • Air Conditioning
    • Water Views
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Owner Transfer Ferry Tickets - Please Inquire Stunning Waterfront Views. Kayak or swim across the pond to Stonewall Beach or just relax on the expansive decks overlooking the water. This is an immaculate older home, very comfortably furnished with 3 bedrooms and 2 baths. High Speed Internet.... View all property information
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    Chilmark, Martha's Vineyard
    From
    $5,150
    / Week
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    1 / 14
    1 Bedroom / 2 Bathrooms / Sleeps 3
    Overview Make Inquiry
    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
    $2,680
    / Week
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    1 / 18
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Satellite TV
    • Grill
    • Microwave
    • Deck
    • Stereo System
    • DVD Player
    • Internet Access
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Contemporary Post and Beam home, private location, bounded by large oaks and stone walls. Enjoy this impeccably maintained 3 bedroom, 3 bath home. Custom designed and featuring a chef's kitchen. The cathedral ceiling great room is open to the spacious dining and kitchen area. Custom features... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    $4,000
    / Week
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    1 / 23
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Dishwasher
    • Water Views
    • Deck
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Waterfront
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Steps from Menemsha Pond – look across the ever-changing surface of the water to Menemsha, the Creek, the Lobsterville dunes, Vineyard Sound and the Elizabeth Islands. Magnificent sunsets from the living room. This cathedral-ceiling Modernist masterpiece is constructed entirely of Western red... View all property information
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    Chilmark, Martha's Vineyard
    From
    $8,000
    / Week
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    1 / 26
    4 Bedrooms / Sleeps 10
    Overview Make Inquiry
    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
    $2,000
    / Week
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    1 / 12
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Grill
    • DVD Player
    • Stereo System
    • Satellite TV
    • Deck
    • Microwave
    • Internet Access
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Charming recently renovated summer cottage features large open living room with sliders leading on to a screened porch and private deck beyond. Porch is fully furnished for dining and relaxing, providing aditional outdoor living space. The deck is private and surrounded by the yard area. The house... View all property information
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    Chilmark, Martha's Vineyard
    From
    $7,200
    / Week
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    1 / 24
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Patio
    • Porch
    • DVD Player
    • Dishwasher
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Outstanding private rental home nestled on 7.2 private acres in the seaside community of Chilmark on the Island of Martha's Vineyard, features a key to Quansoo Beach, one of the most beautiful private association beaches on the island. Warmth, comfort and charm await you and your family in this air... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    $3,500
    / Week
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    1 / 11
    5 Bedrooms / 3 Bathrooms / Sleeps 12
    Overview Make Inquiry
    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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    Location Information
    Chilmark, Martha's Vineyard
    From
    $3,300
    / Week
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    1 / 21
    5 Bedrooms / 4 Bathrooms / Sleeps 12
    Overview Make Inquiry
    Amenities & Details
    • Dishwasher
    • Satellite TV
    • Deck
    • Microwave
    • Ceiling Fans
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    An award winning architectural design coupled with Vineyard charm and seclusion, this house has two wings allowing for multiple family co-existance. This vacation home is open, spacious and filled with light with a wrap-around deck for sun or shade. Amenities and Features include... Additional... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    $6,500
    / Week
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    1 / 18
    4 Bedrooms / Sleeps 7
    Overview Make Inquiry
    Amenities & Details
    • Deck
    • Dishwasher
    • Microwave
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Wonderful cape style house up on the hill in Abel's Hill. This sprawling house offers great space and is perfect for entertaining. Large deck off of the back offer lovely field views. Enjoy lovely summer evenings under the stars next to the fire pit. Association access to tennis equipped with Omni... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535