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Chilmark House Rentals

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    Travellers to Chilmark are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    40 Matching Rentals in ChilmarkView all 41 rentals
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Charming Chilmark 3 Bedroom 3 Bath Vacation Home1 / 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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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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    • Washer
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    • Balcony
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    Pet friendly
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    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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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is an updated 5-bedroom, 1/2 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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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    • Waterfront
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    Pet friendly
    Kid friendly
    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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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
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    Pet friendly
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    About this property
    \n Amenities and Features include...\n \nTop Side Cottage, set in the Iconic Village of Menemsha and Overlooking all of Menemsha Harbor, 300 Yards to the Beach, 50 Yards to the Market, 200 yards to Village, Fish Markets and Eateries
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    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. \n Amenities and Features include...\n \n
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    5 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Wi-Fi
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    Pet friendly
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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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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 9
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Waterfront
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Grill
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
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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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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Grill
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    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    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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    Chilmark, Martha's Vineyard 02535
    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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    Pet friendly
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    Smoking allowed
    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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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
    • Washer
    • Parking
    • Outdoor Dining Area
    • Grill
    • Central Heating
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    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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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Note: New for 2019, Living area is being expanded, fireplace removed along with walls on either side.The living area is being bumped out and into the screened porch area while the screen porch to is being bumped further into the yard.There will be a wall of glass doors the full width of the...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    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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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Waterfront
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    Pet friendly
    Kid friendly
    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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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Private Outdoor Pool (Unheated)
    • Patio
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    Suitability
    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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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Cable/satellite TV
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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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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    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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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    About this property
    Note: New for 2017, all new master bath, new larger dining table and chairs in the dining area and a new teak dining table on the screened porch Charming recently renovated summer cottage features large open living room with sliders leading on to a screened porch and private deck beyond. Porch...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    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 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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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    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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    Chilmark, Martha's Vineyard 02535
    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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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    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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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    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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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Air Conditioning
    • Waterfront
    • Cable/satellite TV
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    • Wi-Fi
    • Patio
    Suitability
    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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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    6 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    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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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    \n Amenities and Features include...\n \nNorth Slope Hilltop House. Private yard, Screeen Porch and Patio, All new AC Throughout, 8 minute drive to Lucy Vincent Beach or Menemsha Village
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Central Heating
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    Pet friendly
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    Smoking allowed
    About this property
    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...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    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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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Internet Access
    • Grill
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    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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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    6 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • DVD Player
    • Washer
    • Hot Tub
    • Cable/satellite TV
    • Internet Access
    • Grill
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    Pet friendly
    Kid friendly
    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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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Chilmark, Martha's Vineyard 02539
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    Location Information
    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Show Prices
    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 8
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