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Holiday Apartments in Chilmark

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    Travellers to Chilmark are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    All 38 Rentals in Chilmark
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    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Smoking allowed
    About this property
    Gracious expanded Cape style home, situated on 11 acres with water frontage on Wades Cove, Chilmark Pond. This stately home comes with a key to private south shore Hancock Beach just over a mile from the house. The beach is also available directly from the house by kayak or skiff rental. (ask your...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    5 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    About this property
    Enjoy private association beach rights at one of the most beautiful south shore beaches, - Quansoo Beach, private tennis court, and an exquisite 6 bedroom home tucked away on several acres in the Qaunsoo area of Chilmark. Expansive deck across the front of the house overlooks the private yard and...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 9
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    This quintessential Chilmark cottage/home has been impeccably maintained, The dining and living areas with spectacular views across Menemsha Channel to Aquinnah open to a wrap around deck. Enjoy spectacular water views and never forget sunsets from just about every area in and outside this...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    High in the hills of peaceful Chilmark with distant panoramic waterviews, this four bedroom impeccably maintained house with in gound pool is surrounded by beautifully landscaped grounds. Expansive decks invite you to make the most of summer living. \n Amenities and Features include...\n...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    About this property
    This is an updated 5-bedroom, 3½ bath, farmhouse set back behind ancient Chilmark stonewalls with a key to Hancock Beach! The house lies between West Tisbury (Alley’s General Store, 7A Foods, Farmer’s Market, Artisan’s Market, galleries, etc.) and Chilmark (Chilmark Store, Chilmark Tavern,...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    Impeccably maintained 4 bedroom, 4.5 bath home set on quiet private acreage, beautiful outdoor living spaces enhanced by the nature that surrounds this quiet retreat. Lucy Vincent Beach, Chilmark Village Center and Menemsha are all just a short drive from this lovely oasis. The interior boasts...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Grill
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    About this property
    Privately situated on 3.5 acres of rolling and manicured landscape on the south side of Chilmark with distant water views, this luxury home is set on a high ridge in an immaculate pairing of quiet nature and sophisticated architecture. The sublime combination of modern and traditional design...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    About this property
    Looking for a private peaceful location and beach rights to beautiful Lucy Vincent beach all the while enjoying a spacious updated vacation home, look no further, This lovely updated 3 bedroom 2.5 bath home located off of North road features a large open kitchen with center prep island , breakfast...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Smoking allowed
    About this property
    Note: New for 2019, Living area has been expanded, fireplace removed along with walls on either side as displayed in current photos The living area has been bumped out and into the screened porch area. There is now a wall of glass doors the full width of the living area that will open onto the...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Smoking allowed
    About this property
    This spacious, comfortably furnished home is conveniently located between Chilmark and West Tisbury. The master bedroom and a 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 cathedral ceiling,...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Immaculate 4 bedroom in a private setting yet just a 10 minute drive to town or the most beautiful Lucy Vincent Beach. Features include large deck and wifi internet. The house has an open floor plan and an additional family/tv room for your comfort. \n Amenities and Features include...\n \nLarge...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
    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. \n Amenities and Features include...\n...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Private Outdoor Pool (Unheated)
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    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...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Charming updated 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 additional outdoor living space. The deck is private and surrounded by the yard area. The house...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Tastefully furnished and decorated with antiques and art. This 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; has...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    CLASSIC VINEYARD FISHING VILLAGE VIEWS FROM THIS QUINTESSENTIAL COTTAGE1 / 12
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 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...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    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. \n Amenities and Features...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One of a kind retreat, oceanfront, private beach. This extraordinary location usually reserved only for renters of estates is one of the most desirable cottage homes in Chilmark. The deck and breathtaking views will make you never want to leave. A short stroll and you are at Stonewall Beach,...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A perfect vacation house with miles of hiking trails and the best vineyard beach at your doorstep. Enjoy the 'play' pool which is 4 feet deep and nice to relax in on a beautiful sunny vineyard day. Built with water therapy and children in mind; handicapped accessible. Total privacy, in one of the...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a peaceful, recently built, four-bedroom, four-bathroom Cape located directly on Chilmark Pond with a highly desirable Hancock Beach Association key. The house has all modern amenities—air conditioning, wireless, high speed Internet, four TVs, etc. Tastefully decorated, the house has a mix...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    6 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Contemporary Home commands one of Martha's Vineyard's most spectacular views overlooking the Elizabeth Islands and Vineyard Sound. Breathtaking sunsets. Outdoor patios and deck and multiple living areas provide many options for family gatherings or quiet times. \n Amenities and Features...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 10
    Charming Chilmark 3 Bedroom 3 Bath Vacation Home1 / 10
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Porch
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    Kid friendly
    Smoking allowed
    About this property
    Located in Chilmark on Martha's Vineyard, this 3 bedroom, 3 bathroom property is a perfect spring, summer or fall getaway. Cathedral ceilings create bright, airy spaces. Amenities include air conditioning, high speed internet, washer/dryer, gas fireplaces, TV in all rooms, outdoor shower, slate...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
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    • Outdoor Dining Area
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    • Central Heating
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    Smoking allowed
    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...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    The house is magnificently located atop a slightly sloping knoll overlooking Stonewall Beach in Chilmark, and on Stonewall Pond. Property benefits include access to the flotilla of kayaks and paddle boards on the Pond, and private access to the Stonewall Beach, with beach chairs, toys and umbrellas...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Smoking allowed
    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;...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    6 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Patio
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    • Hot Tub
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    Smoking allowed
    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...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 10
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Washer
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    • Balcony
    • Terrace
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    Smoking allowed
    About this property
    This charming 5 bedroom, 4 bath home located at Prospect Hill in Chilmark has a great layout and excellent location. Main level has generous kitchen, open living dining area, and master bedroom and bath, all light and bright with extensive decking and French doors to connect the interior to the...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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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...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Smoking allowed
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    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...
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    02539, Chilmark, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    Outstanding New Home nestled in the Prospect Hill area of Chilmark, bordered by Menemsha Hills Conservation Land and Trails. This all new contemporary home features gorgeous views of the North Shore to the Elizabeth Islands, Association Tennis Courts and fantastic Walking Trails. With four...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Classic coastal cottage remodeled in 2000. Charming open and sunny interior feautres 3 bedrooms and 2 baths in the main house. 2nd level Master bedroom opens onto private deck with views of Menemsha Harbor. Seperate guest cottage has Queen bed and a full bath. Outdoor spaces for your vacation...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
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    About this property
    Lovely rural home near farms, yoga studio. Across from preservation land with hiking trail. Walk to Grange Hall, Farmer's Market, general store and cafe. ( 2000 ft² ) New master suite in pleasant cottage style home. Grassy yard and small garage. Isolated setting but convenient. Close to desirable...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    5 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Grill
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    • Ocean Views
    • DVD Player
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    • Balcony
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    • Porch
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    02535, Chilmark, Martha's Vineyard
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 9
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