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Holiday Rentals and Homes in Chilmark, MA

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    All 159 Rentals in Chilmark
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    Travellers to Chilmark are booking August dates now. Secure your holiday rental today, and have the perfect trip.
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    From
    €3,602
    / Week
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    1 / 20
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    From
    €7,203
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    1 / 23
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    From
    €4,502
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    1 / 19
    5 Bedrooms / 2 Bathrooms / Sleeps 9
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    €579
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    1 / 44
    5 of 5 stars (6) Excellent
    5 Bedrooms / 4 Bathrooms / Sleeps 9
    Overview Reviews (6) Make Enquiry
    Amenities & Details
    • Wi-Fi
    • Water Views
    • Stereo System
    • Watersports Nearby
    • Housekeeping...
    • DVD Player
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This comfortable contemporary home located up-island in Chilmark, includes a key to a private beach, Blackpoint, and is ideal for laid-back Vineyard living, or elegant entertaining with both ocean and hillside view. The open floor plan for the common areas bring the outdoors inside with spectacular... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    €1,801
    / Week
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    1 / 17
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    Overview Make Enquiry
    Amenities & Details
    • Stereo System
    • Air Conditioning
    • Dryer
    • Internet Access
    • Satellite TV
    • DVD Player
    • Washer
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Charming cottage with water view just steps into Menemsha. Great outdoor deck, new kitchen - everything recently updated. Wonderful antiques for decoration and top quality furnishings throughout. Additional amenities include: coffee maker, smoke free, 6 dining capacity, pets considered, lobster... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    €3,602
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    1 / 22
    5 of 5 stars (1) Excellent
    4 Bedrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Waterfront
    • Internet Access
    • Stereo System
    • Water Views
    • Satellite TV
    • Fireplace
    • Air Conditioning
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Chilmark waterfront rental home located on Quitsa Pond with views across Quitsa and Menemsha ponds out to the Elizabeth Islands. This martha's vineyard rental property offers dock, mooring along with access to small beach area just down the path on Clam Point Cove. Named appropriately, it is an... View all property information
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    Chilmark, Martha's Vineyard
    From
    €4,502
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    1 / 24
    4 Bedrooms / 4 Bathrooms / Sleeps 9
    Overview Make Enquiry
    Amenities & Details
    • Stereo System
    • Washer
    • Internet Access
    • Deck
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Private up-island setting with sweeping distant water views. This four bedroom retreat is spacious, comfortable and well-appointed throughout with central a/c. Relax and enjoy summer days on the expansive upper deck with great views and fabulous sunsets. The upper level has an open living area -... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    €2,251
    / Week
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    1 / 26
    4 Bedrooms / 5 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Stereo System
    • Waterfront
    • Washer
    • Fireplace
    • DVD Player
    • Internet Access
    • Satellite TV
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Sunrise from the ocean, sunset over Stonewall Pond and view towards Squibnocket Beach. Old Vineyard look and feel, an elegant and comfortable beach house with landscaped gardens. Recently built 500 sq ft addition includes ground floor MBR suite offering full amenities. Services include: cleaning 3X... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    €3,151
    / Week
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    1 / 21
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Grill
    • Dryer
    • Internet Access
    • Deck
    • DVD Player
    • Air Conditioning
    • TV
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Beautiful Chilmark setting, located on Stonewall Pond with spectacular waterviews! The east offers views of Stonewall Pond to the Atlantic ocean. The west offers views of Quitsa Pond to Menemsha Pond. Great outdoor deck perfect for relaxing and/or outdoor entertaining. Large sweeping lawn and... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    €7,203
    / Week
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    1 / 12
    5 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Satellite TV
    • Washer
    • Dryer
    • DVD Player
    • Internet Access
    • Stereo System
    • Grill
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This contemporary home commands one of Martha s Vineyard s most spectacular 180 degree views overlooking the Elizabeth Islands and Vineyard Sound. You will experience breathtaking sunsets as you dine in or out. Situated high on one of Chilmark’s hills, this home is bright and airy with colorful... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
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    From
    €7,203
    / Week
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    1 / 21
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Shared Outdoor Pool...
    • Satellite TV
    • Internet Access
    • Washer
    • Air Conditioning
    • Deck
    • DVD Player
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    A spectacular Chilmark estate located on 6.9 acres complete with private pool and tennis courts. An updated master bedroom and bathroom will soothe you after a busy day at the beach. Comfortable furnishings paired with state-of-the-art appliances make this a truly magnificent vacation experience.... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    €1,351
    / Week
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    1 / 11
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Grill
    • Washer
    • Internet Access
    • Deck
    • Cooker
    • Stereo System
    • Satellite TV
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Nicely renovated cottage nestled in the woods, enjoy the peace and quiet of up-island living. Clean, open interior living area, newly furnished with fully equipped kitchen. Enclosed outdoor shower a must for days at the beach. Perfect getaway cottage, sure to please. Additional amenities include:... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    €6,303
    / Week
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    1 / 26
    6 Bedrooms / 5 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Deck
    • DVD Player
    • Porch
    • Washer
    • Satellite TV
    • Dryer
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Wonderful, Vineyard oversized Cape with expansive views of picturesque farmland (Keith Farm) and Atlantic Ocean. Separate main house and guest house allow for comfortable space between guests and families. Extremely charming home with all necessary amenities; beautifully renovated kitchen. Very... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    €2,431
    / Week
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    1 / 14
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Deck
    • Stereo System
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Dryer
    • Internet Access
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This charming newly remodeled three bedroom, two bath Cape has a spacious master bedroom suite, cozy sun room and updated kitchen. Spend your Chilmark vacation here and enjoy rights to desirable Lucy Vincent and Squibnocket beach. A memorable up-island retreat awaits you! Additional amenities... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    €945
    / Week
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    1 / 10
    4 Bedrooms / 2 Bathrooms / Sleeps 9
    Overview Make Enquiry
    Amenities & Details
    • Dryer
    • Air Conditioning
    • Stereo System
    • Satellite TV
    • DVD Player
    • Internet Access
    • Deck
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Spacious and comfortably furnished contemporary Cape is conveniently located between Chilmark and West Tisbury. House is fully equipped, open living area with cathedral ceilings, wood floors, operable skylights, large outdoor deck and separate family room with sleeper sofa. Private setting with... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    €945
    / Week
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    1 / 13
    4 Bedrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Deck
    • DVD Player
    • Internet Access
    • Satellite TV
    • Microwave
    • Stereo System
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Four Bedroom Cape located in Chilmark on a circular drive. This Martha's Vineyard vacation rental offers private back yard with large deck for out door dining and sunning. Access to Lucy Vincent and Squibnocket Beaches just up the road. Additional amenities include: beach chairs, outdoor shower:... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    €6,753
    / Week
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    1 / 18
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Internet Access
    • Stereo System
    • Washer
    • Fireplace
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Expansive distant waterviews overlooking Vineyard Sound on three and a half acre property. Located in desirable Spring Point, this 40 home association is accessed by a private, well maintained dirt roads with 40 acres of common land consisting of nature trails and a private beach on the Sound. This... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    €2,251
    / Week
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    1 / 17
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Internet Access
    • Washer
    • DVD Player
    • Waterfront
    • Dryer
    • Satellite TV
    • Stereo System
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Adorable, private boathouse at the edge of Stonewall Pond. Wrap around deck provides gorgeous views (as well as sound effects) of the pond and the barrier beach beyond, great for swimming! Perfect for a small family or a romantic getaway. An idyllic island retreat. Additional amenities include:... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    €4,952
    / Week
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    1 / 9
    4 Bedrooms / Sleeps 9
    Overview Make Enquiry
    Amenities & Details
    • Microwave
    • Water Views
    • Deck
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Stereo System
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Lovely, Chilmark home in close proximity to Menemsha House offers four bedrooms with comfortable kitchen, living and dining area. Great deck off back of house with views of Vineyard Sound. Very relaxing Martha's Vineyard vacation rental. Additional amenities include: longitude: -70.7598000, dinner... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    €18,008
    / Week
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    1 / 7
    5 Bedrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Stereo System
    • Internet Access
    • Satellite TV
    • Grill
    • Shared Outdoor Pool...
    • Water Views
    • Air Conditioning
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Spectacular contemporary Martha's Vineyard vacation rental offering 5,000 square feet of casually elegant living space. Overlooking Chilmark pond and Lucy Vincent Beach with professionally landscaped grounds. Enjoy lounging on the deck with an in-ground negative edge swimming pool. Additional... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    €5,853
    / Week
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    1 / 18
    4 Bedrooms / Sleeps 7
    Overview Make Enquiry
    Amenities & Details
    • Deck
    • Dishwasher
    • Microwave
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Wonderful cape style house up on the hill in Abel's Hill. This sprawling house offers great space and is perfect for entertaining. Large deck off of the back offer lovely field views. Enjoy lovely summer evenings under the stars next to the fire pit. Association access to tennis equipped with Omni... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    €6,753
    / Week
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    1 / 15
    5 Bedrooms / Sleeps 9
    Overview Make Enquiry
    Amenities & Details
    • Deck
    • Internet Access
    • Water Views
    • Dishwasher
    • Air Conditioning
    • Satellite TV
    • Waterfront
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    A rare Chilmark find! This house sits up on a bluff with the most spectacular Atlantic views over Squibnocket Beach. There are two paths down to the beach as well as keys to two of the most pristine island beaches within the gated association. The Bluff house blends the traditional Chilmark retreat... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    €2,701
    / Week
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    1 / 13
    4 Bedrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Water Views
    • Satellite TV
    • Internet Access
    • Dishwasher
    • Microwave
    • Stereo System
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Lovely four bedroom home in Menemsha Hills, Chilmark. House offers distant views from upper level over Menemsha on one side and across to Vineyard Sound on the other. Nicely appointed furnishings. The house has a patio off the dining room and kitchen overlooking grounds and gardens. Just minutes to... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    €11,705
    / Week
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    1 / 27
    5 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Deck
    • Dryer
    • DVD Player
    • Internet Access
    • Satellite TV
    • Boat Available
    • Waterfront
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Architect designed, beautifully appointed home and guest house on five acres in Chilmark. Knoll wooded lot on Tisbury Great Pond, fronted on large native grass meadow. This bright and airy home offers complete privacy and access to Quansoo beach. Kayakers will delight in exploring the Great Pond... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    €4,412
    / Week
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    1 / 21
    5 Bedrooms / 5 Bathrooms / Sleeps 9
    Overview Make Enquiry
    Amenities & Details
    • Fireplace
    • Internet Access
    • Washer
    • Air Conditioning
    • Satellite TV
    • Stereo System
    • DVD Player
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Relax and enjoy sweeping views of the South Shore from the upper deck balcony. Sprawling interior design provides an open and comfortable space, ideal for family living. A fully loaded kitchen with top of the line appliances, perfect for entertaining. Unwind in the screened-in porch which overlooks... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    €2,701
    / Week
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    1 / 15
    5 Bedrooms / 3 Bathrooms / Sleeps 9
    Overview Make Enquiry
    Amenities & Details
    • Internet Access
    • Dryer
    • Stereo System
    • Satellite TV
    • DVD Player
    • Deck
    • Washer
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Spectacular views overlooking Squibnocket Pond and Atlantic Ocean. Contemporary home with two spacious living rooms. Walk to Squibnocket beach. Private access to Squibnocket pond, canoe provided. Key is also available for access to private Zach s Cliff Beach, maximum two cars. Additional... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    €1,125
    / Week
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    1 / 9
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Deck
    • Satellite TV
    • Grill
    • DVD Player
    • Washer
    • Internet Access
    • Stereo System
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Nice two bedroom cottage located in the heart of Menemsha. Watch the beautiful sunsets from the deck while dining. Five minute walk to beach, fish market or quaint shops in this fishing village. Additional amenities include: coffee maker, smoke free, 4 dining capacity, lobster pot, 1... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    €2,251
    / Week
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    1 / 23
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Internet Access
    • Grill
    • Washer
    • Stereo System
    • DVD Player
    • Dryer
    • Satellite TV
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Charming, remodeled in 2000, this is a seaside cottage overlooking Menemsha Harbor and beach. Bright and open interior with upscale details, the house is very comfortable. Master suite upstairs with deck and views of harbor, beach and sunsets. Backyard is private with outdoor deck and screened in... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    €1,080
    / Week
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    1 / 12
    3 Bedrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Microwave
    • Deck
    • Satellite TV
    • Internet Access
    • Fireplace
    • Water Views
    • Stereo System
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Delightful Cape GUEST HOUSE situated on the grounds of a hilltop Chilmark estate. (Estate's Main House is rented separately and may be occupied). Magnificent views over Menemsha Pond. Access to Hancock Beach with adjacent parking and Menemsha Pond within walking distance. First floor has an open... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    €3,602
    / Week
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    1 / 14
    5 Bedrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Microwave
    • Internet Access
    • Water Views
    • Deck
    • Satellite TV
    • Dishwasher
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Stunning Chilmark rental property with beautiful views to the south across Squibnocket Pond and the Atlantic and to the north across Menemsha Pond to the Elizabeth Islands. The house was built in the 1950s in a manner to maximize the enjoyment of the wonderful setting and views. It is surrounded by... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    €7,203
    / Week
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    1 / 26
    4 Bedrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Deck
    • Internet Access
    • Satellite TV
    • Dishwasher
    • Fireplace
    • Water Views
    • Stereo System
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Spectacular waterviews! This Martha's Vineyard vacation rental is situated on 3+ acres overlooking the Elizabeth Islands and the Vineyard sound. On a clear day you can catch a lovely view of the Aquinnah lighthouse. The outdoor living space is truly where you want to be. Each area used for various... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    €1,621
    / Week
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    1 / 8
    4 Bedrooms / Sleeps 9
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Satellite TV
    • Microwave
    • Stereo System
    • Internet Access
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Quintessential Chilmark farm house on 12 acre estate. Renovated 1700's house offering antique qualities with the modern conveniences. Very private and tranquil. Enjoy the beautiful south shore Chilmark beaches with this rental. Additional amenities include: cleaning fee: $180, check in time: 4:00,... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    €4,502
    / Week
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    1 / 14
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Deck
    • TV
    • Internet Access
    • DVD Player
    • Waterfront
    • Fireplace
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Classic Vineyard Cape with exquisite rolling landscape and old stone walls. Views of Menemsha Pond and Vineyard Sound. Private white sandy beach. Peaceful up-island vacation retreat. Homeowner will include one bedroom-2 bath guesthouse for an additional fee. Please contact an agent for more... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    €1,801
    / Week
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    1 / 8
    2 Bedrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Air Conditioning
    • DVD Player
    • Stereo System
    • Deck
    • Internet Access
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Lovely Chilmark Cottage for rent. Situated with privacy in a wooded area not too far from beaches and Alley's General Store. Enjoy peaceful mornings and evenings on the private deck while heading to the beautiful South Shore on Lucy Vincent Beach during the sunny Vineyard days. Walk into this... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
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    1 / 4
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Dryer
    • Stereo System
    • Fireplace
    • Washer
    • Deck
    • DVD Player
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Secluded location on a cul de sac overlooking a private meadow with spreading oak trees. The traditional exterior welcomes you to our spacious contemporary. the main living area features a great room with fireplace which opens to a dining room and kitchen with an island eating bar. Off the great... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    €3,151
    / Week
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    1 / 14
    4 Bedrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Water Views
    • Stereo System
    • Internet Access
    • Waterfront
    • Satellite TV
    • Air Conditioning
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Sweeping views over Quitsa and Menemsha Ponds to the Elizabeth islands and Vineyard sound. Contemporary Martha's Vineyard vacation rental in Chilmark with open kitchen, dining and living area. Natural light from picture windows and sky lights. Shared Dock access. Great property for fun in the sun... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    €25,211
    / Week
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    1 / 30
    6 Bedrooms / Sleeps 13
    Overview Make Enquiry
    Amenities & Details
    • Deck
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Water Views
    • Waterfront
    • Internet Access
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Chilmark retreat at its finest. This tranquil and extremely private setting is on the south side side of Martha's Vineyard within close proximity of the stunning Lucy Vincent Beach. This sprawling well designed six bedroom fully air conditioned ranch style home gives you plenty of indoor lounging... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    €13,506
    / Week
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    1 / 27
    6 Bedrooms / 5 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Stereo System
    • Washer
    • Fireplace
    • Internet Access
    • DVD Player
    • Satellite TV
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Exceptional, private home set high on a hill with views of Menemsha Pond and Atlantic Ocean. Great outdoor space for entertaining and/or relaxing on the patio as well as deck areas. Beautifully landscaped setting with gardens and stonework throughout yard. Post and beam, tastefully furnished with... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    €6,753
    / Week
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    1 / 27
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Washer
    • Deck
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Internet Access
    • Stereo System
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Peaceful up-island setting on eight acres overlooking meadow and pond. The property borders 46 acres of conservation land in back, and approximately 25 acres in front. Open, bright, sun-filled living area with hardwood flooring throughout the home. Tastefully decorated and comfortably furnished.... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    €5,402
    / Week
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    1 / 22
    4 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Stereo System
    • Waterfront
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Washer
    • DVD Player
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Watch the sun set from your private, romantic waterfront cottage with unparalleled views of Menemsha Pond, wetlands, ocean, Elizabeth Islands and Gay Head. Key to a private Gay Head Beach is included with rental. Additional amenities include: coffee maker, smoke free, ipod dock station, lobster... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    €1,351
    / Week
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    1 / 9
    2 Bedrooms / Sleeps 5
    Overview Make Enquiry
    Amenities & Details
    • Satellite TV
    • Microwave
    • Dishwasher
    • Stereo System
    • Deck
    • Grill
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Post and Beam Martha's Vineyard vacation rental in a lovely rural setting in Chilmark. Two bedrooms with large decks and distant waterview of Lucy Vincent beach. Additional amenities include: wood stove, television: regular, outdoor shower: enclosed, check in time: 2:00, flipkey header: #2006 post... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    €900
    / Week
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    1 / 14
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Stereo System
    • Fireplace
    • DVD Player
    • Deck
    • Internet Access
    • Satellite TV
    • Dryer
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This wonderful three bedroom up-island retreat, is the perfect summer vacation home, with lots of room to spread out. The master bedroom on the first floor offers great light in the morning sun with ensuite bathroom. The second floor with two bedrooms, shared bathroom and small office area on the... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    €1,441
    / Week
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    1 / 14
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Microwave
    • Cooker
    • Deck
    • Stereo System
    • Satellite TV
    • DVD Player
    • Waterfront
    • Linens Provided
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Kick back and relax in this beautiful one bedroom cottage overlooking Menemsha Harbor. Shop at the Menemsha General Store, fish from Dutcher Dock, and swim at Menemsha Beach, or enjoy a lobster dinner while watching sunset from the balcony of your upstairs living room. A little slice of heaven... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    €8,554
    / Week
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    1 / 17
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Deck
    • Satellite TV
    • Washer
    • Internet Access
    • Waterfront
    • DVD Player
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Stunning Quansoo/Great Pond setting. Lots of room to roam and explore at this waterfront property, which includes access to Quansoo beach, a private dock for launching your kayaks from, and a relaxing setting from which to take in the beautiful views this property has to offer. Air conditioned... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02575
    From
    €4,502
    / Week
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    1 / 14
    2 Bedrooms / 1 Bathroom / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Internet Access
    • Fireplace
    • DVD Player
    • Dryer
    • Grill
    • Deck
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Chilmark family retreat. Overlooking the expansive meadows of Grey Barn s 62 acres of protected farmland. 2 bedrooms with an additional sleeping loft. Exclusive up-island beach access to Squibnocket and Lucy Vincent. Additional amenities include: coffee maker, smoke free, pets considered, 4 dining... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    €16,207
    / Week
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    1 / 24
    4 Bedrooms / 2 Bathrooms / Sleeps 7
    Overview Make Enquiry
    Amenities & Details
    • DVD Player
    • Dryer
    • Stereo System
    • Internet Access
    • TV
    • Waterfront
    • Washer
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Beautiful converted barn located in exclusive Squibnocket Farm. Access to one of the Vineyards most pristine and private ocean beaches. This home has the original exposed beams and floor to ceiling windows offering spectacular views of the surrounding meadows, ocean, pond and gardens. Balconies and... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    €2,251
    / Week
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    1 / 17
    5 Bedrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Deck
    • Stereo System
    • Grill
    • Internet Access
    • Satellite TV
    • Water Views
    • Microwave
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    A grand summer house on Martha's Vineyard where memories are made. This landmark, hilltop Victorian offers magnificent 270-degree views over meadows, Menemsha Pond and the North shore. Access to Hancock Beach with adjacent parking, as well as Menemsha pond within walking distance. Two spacious... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    €2,701
    / Week
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    1 / 19
    4 Bedrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Microwave
    • Stereo System
    • Dishwasher
    • Deck
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Elegant Architectural Digest Cape home in Chilmark, in pristine condition. Many fine details to this Martha's Vineyard vacation home. Custom woodwork, antique heart pine floors and fireplaces. Luxury construction (as compared to custom) built in 1998. Custom cabinetry with gourmet kitchen. Meadowed... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    €9,004
    / Week
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    1 / 21
    3 Bedrooms / 4 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Dryer
    • Patio
    • DVD Player
    • Air Conditioning
    • Deck
    • Satellite TV
    • Internet Access
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Beautifully renovated and restored antique Cape situated in Chilmark on two ponds. Three bedroom home plus loft area. Tastefullly furnished throughout with full modern amenities. Living room, dining room as well as an eat-in kitchen. Includes a game room with pool table and sitting area for... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    €7,203
    / Week
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    1 / 10
    5 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Internet Access
    • DVD Player
    • Deck
    • Washer
    • Patio
    • Stereo System
    • Satellite TV
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Spacious up-island home situated high on hill of desirable Spring Point. Enjoy great sunsets and sweeping waterviews of the Atlantic on the outer decks and patio. Thoughtfully designed for privacy, two master bedrooms on either end of home, two living rooms one up and one down. Large kitchen,... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535