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Vacation Rentals in Chilmark, MA

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    Travelers to Chilmark are booking May dates now. Secure your vacation rental today, and have the perfect trip.
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    4.5 of 5 stars (4) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    This home is 1/2 mile from Chilmark Center If you are having trouble with FERRY RESERVATIONS contact me via email or phone and I'll work with you. I do have some reservations for August and July. This home is minutes to both Lucy Vincent Beach (with both nude and regular bathing sections) and... View all property information
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    Chilmark, Martha's Vineyard 02535
    4 of 5 stars Reviewed July 7, 2014
    Just spent a very relax vacation in this country style house that gived us a family home feel outside of our home. The house is surround by green trees with beautiful wood logs...
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    1 / 17
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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
    1 / 12
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Come and enjoy the wonderful waterviews from this Chilmark cottage. The first floor has a nice living room and eat in kitchen with waterviews. There are also two bedrooms and a full bathroom on the first floor. The second floor has two additional bedrooms and full bathroom with a shower. The... View all property information
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    Chilmark, Martha's Vineyard 02535
    1 / 13
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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 02535
    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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    1 / 22
    5 of 5 stars (1) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    About this property
    A boutique hotel experience in an unrivaled setting at the end of a one mile single lane road. Enjoy the sunrise from the ocean, sunset over the adjoining 13 acre Sheriff's Meadow Foundation conservation preserve. This home has a wonderful view toward Squibnocket Beach, a mile away, and the... 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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    1 / 11
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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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    Chilmark, Martha's Vineyard 02535
    1 / 8
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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
    Location Information
    Chilmark, Martha's Vineyard 02535
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    1 / 30
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Come enjoy the secluded beauty of this award-winning, architect-designed home in Chimark on almost four acres of land. Relax on the two level deck or on the beach at Lucy Vincent, Squibnocket, or nearby Menemsha. The remarkable design makes great use of over 3500-square-foot space by joining the... View all property information
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    Chilmark, Martha's Vineyard 02535
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
    1 / 19
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    With old-world charm aplenty and modern amenities, you'll enjoy a relaxing holiday at this Chilmark vacation rental. It's a great spot for a family looking for a quiet refuge. You're near the center of town and close to iconic businesses, but you're also not far from the cliffs at Aquina as well as... View all property information
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    Chilmark, Martha's Vineyard 02535
    1 / 12
    4 of 5 stars (1) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    What a location! Located in Menemsha with classic Vineyard fishing village views this cottage is the quintessential vacation home. You can walk to the beach to picnic, fish or watch beautiful sunsets and you can also walk to one of the Island's most popular seafood restaurants. It is light, airy... View all property information
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    Chilmark, Martha's Vineyard 02535
    1 / 17
    6 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • 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
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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
    1 / 26
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    You'll be all atwitter about the Bird's Nest at Chilmark Pond. Gather your family or friends and enjoy this Martha's Vineyard vacation home, with ocean views, during a June getaway. Whether you bring your own watercraft or rent from the home-delivery service, Book-a-Boat, you can launch from the... View all property information
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    Chilmark, Martha's Vineyard 02535
    1 / 14
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Satellite TV
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    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
    1 / 33
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Island Romance is a Chilmark vacation rental with ocean views on a quiet plot of land, featuring a shared dock, spacious yard, and studio cottage. Bring your friends and loved ones to this sweet New England farmhouse on Martha's Vineyard. In summer you'll be able to use the home's semi-private dock... View all property information
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    Chilmark, Martha's Vineyard 02535
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    1 / 20
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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
    1 / 8
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • 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
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    2 Bedrooms, 1 Bathroom, Sleeps 3 | Quick View
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    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
    1 / 18
    5 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    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
    1 / 18
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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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    Chilmark, Martha's Vineyard 02535
    1 / 30
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    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
    1 / 22
    5 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Ocean Views
    • DVD Player
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    • Balcony
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    • x
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    • x
    About this property
    Enter our vacation world up a 0.2 mile paved driveway through the woods to the private hilltop with only two other houses. Open the gate and delight at the expanse of ocean view from the deck over oak trees - our 3 1/2 acres adjacent to a sanctuary seem like 100. Listen to the birds and the surf... View all property information
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    Chilmark, Martha's Vineyard 02535
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    5 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    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
    1 / 13
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    Clean and family friendly. Centrally located, the cottage is only fifteen minutes from most island towns including Edgartown and Aquinnah, where dining and shopping are world renowned. Lovely wooded setting offers privacy with large comfortable deck and yard. Outdoor shower adds to the Vineyard... View all property information
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    Chilmark, Martha's Vineyard 02535