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Vacation Rentals in Chilmark, MA

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    All 86 Rentals in Chilmark
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    Travelers to Chilmark are booking September dates now. Secure your vacation rental today, and have the perfect trip.
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    From
    $345
    / Night
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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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    1 / 22
    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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    $3,750
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    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
    From
    $1,595
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    1 / 12
    2 Bedrooms / 1 Bathroom / Sleeps 3
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    Amenities & Details
    • 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
    $4,800
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    1 / 21
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    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
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    $571
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    1 / 5
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Inquiry
    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
    $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
    $3,000
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    1 / 18
    5 Bedrooms / 2 Bathrooms / Sleeps 9
    Overview Make Inquiry
    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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    Chilmark, Martha's Vineyard
    From
    $4,150
    / Week
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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
    • ?
    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 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
    $2,650
    / Week
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    1 / 11
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    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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    Chilmark, Martha's Vineyard
    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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    Location Information
    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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    From
    $686
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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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    Location Information
    Chilmark, Martha's Vineyard 02539
    From
    $857
    / Night
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    1 / 20
    6 Bedrooms / 4 Bathrooms / Sleeps 12
    Overview Make Inquiry
    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
    $4,450
    / Week
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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
    • ?
    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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    Location Information
    Chilmark, Martha's Vineyard
    From
    $143
    / Night
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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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    Location Information
    Chilmark, Martha's Vineyard 02535
    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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    Location Information
    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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    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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    Location Information
    Chilmark, Martha's Vineyard 02535
    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
    $20,700
    / Week
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    1 / 38
    Studio / 3 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Satellite TV
    • Water Views
    • Patio
    • Stereo System
    • Private Outdoor...
    • Internet Access
    • Air Conditioning
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Expansive views of Chilmark Pond and the Atlantic Shoreline. Deeded access to pond, dock and private ocean beach (please inquire for more information). Newly completed 5400 square foot luxury home with ... multiple decks overlooks the masterfully landscaped grounds, stone walls, and ocean views... View all property information
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    Chilmark, Martha's Vineyard
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    From
    $150
    / Night
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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
    $1,357
    / 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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    Location Information
    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
    $14,000
    / Week
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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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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    $10,000
    / Week
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    1 / 33
    4 Bedrooms / 2 Bathrooms / Sleeps 9
    Overview Make Inquiry
    Amenities & Details
    • Stereo System
    • Dishwasher
    • Satellite TV
    • Water Views
    • DVD Player
    • Grill
    • Deck
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Pristine renovated barn set on acres of extreme privacy with ocean views and private ocean beach. This is an extraordinary residence with exposed beams and glass walls framing expansive views of meadows and the Atlantic ocean beyond. The refined interior offers open living spaces, large dining area... View all property information
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    Chilmark, Martha's Vineyard
    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
    $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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    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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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    $16,000
    / Week
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    1 / 24
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Inquiry
    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
    $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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    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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    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
    $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
    $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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    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
    $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
    $4,500
    / 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
    $2,700
    / Week
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    1 / 22
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Waterfront
    • Water Views
    • Stereo System
    • Porch
    • Satellite TV
    • Internet Access
    • Deck
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Owner Transfer Ferry Tickets - Please Inquire Immaculate waterfront gem on Stonewall Pond. Breathtaking views across pond to barrier beach. Perfect for honeymoon getaway. Sleeps four - please ask agent for details. Walk or kayak to Stonewall Beach. Pets Considered. Amenities and Features... View all property information
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    Chilmark, Martha's Vineyard
    From
    $3,300
    / Week
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    1 / 24
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Stereo System
    • Grill
    • Waterfront
    • DVD Player
    • Water Views
    • Satellite TV
    • Internet Access
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Owner Transfer Ferry Tickets - Please Inquire Gorgeous Views of Stonewall Pond from this immaculate 4 bedroom three bath home. Cathedral ceilings add to the spacious feeling of this contemporary home and the open kitchen, living and dining areas provide the perfect space for your summer vacation.... View all property information
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    Chilmark, Martha's Vineyard
    From
    $7,000
    / Week
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    1 / 18
    6 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Satellite TV
    • Patio
    • Internet Access
    • DVD Player
    • Fireplace
    • Stereo System
    • Washer
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This gracious Vineyard elongated Cape overlooks the Keith Farm and the Atlantic Ocean beyond. The gourmet kitchen has just been beautifully renovated and is a dream. The living areas are all decorated with charm and all have views. The separate main house, with four bedrooms, and guest house, with... 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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    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
    $4,000
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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
    $12,500
    / Week
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    1 / 15
    5 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Satellite TV
    • Stereo System
    • Deck
    • Washer
    • Waterfront
    • DVD Player
    • Fireplace
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Contemporary, private, exquisite home set right on Tisbury Great Pond. Drive to Quansoo or kayak right from the house. Large, gorgeous gourmet kitchen, spacious living room with stylish fire place, large screened porch, water views through the trees all contribute to the heightened appeal of this... View all property information
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    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
    $12,000
    / Week
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    1 / 32
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Inquiry
    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
    $1,250
    / Week
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    1 / 13
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Deck
    • Microwave
    • Satellite TV
    • Internet Access
    • Grill
    • Water Views
    • DVD Player
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Amenities and Features include... Menemsha, Waterview, Walk to beach Additional amenities include: coffee maker, fans - portable, lobster pot, food processor, washer / dryer, cd player, outside shower - enclosed, vacuum, outdoor furniture, ironing board. View all property information
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    Chilmark, Martha's Vineyard
    From
    $2,700
    / Week
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    1 / 20
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    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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    Chilmark, Martha's Vineyard