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Vacation Rentals in Chilmark, MA

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    All 176 Rentals in Chilmark
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    Travellers to Chilmark are booking June dates now. Secure your vacation rental today, and have the perfect trip.
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    From
    $419
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    1 / 10
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    $389
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    1 / 26
    5 of 5 stars (2) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 4
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    $4,553
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Elder access
    • ?
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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... View all property information
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    $1,936
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    Amenities & Details
    • Refrigerator
    • Ceiling Fans
    • Stereo System
    • Cooker
    • Washer
    • Grill
    • Satellite TV
    • Microwave
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
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    • x
    About this property
    Great location. Menemsha Village. 2 bedroom cottage. Sunny interior. 1 bath, plus outdoor shower. Storage barn, cable tv, High Speed internet, washer. Walk to beach, harbor, dock, stores, restaurants. Currently available August only. $1595 per week. 2 wk minimum. Maximum occupancy 2 adults,... View all property information
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    $7,892
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    Amenities & Details
    • Internet Access
    • Microwave
    • Grill
    • Fireplace
    • Dishwasher
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Peaceful Chilmark rental home offering privacy along with great proximity to West Tisbury town center and Chilmark beaches. You will feel the quiet tranquility that is so treasured in Chilmark. Lovely open space on the first floor that opens up to a large deck and patio with lovely field views. You... View all property information
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    1 / 45
    5 of 5 stars (6) Excellent
    5 Bedrooms / 4 Bathrooms / Sleeps 9
    Overview Reviews (6) Make Enquiry
    Amenities & Details
    • Fireplace
    • Washer
    • Air Conditioning
    • Water Views
    • Dryer
    • Internet Access
    • Deck
    • Stereo System
    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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    1 / 23
    5 of 5 stars (1) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • TV
    • Microwave
    • Deck
    • DVD Player
    • Dryer
    • Dishwasher
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Smoking allowed
    • Elder access
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    About this property
    Unique waterfront living in the heart of Chilmark. The Boathouse sits directly on the shores of Stonewall Pond, with sweeping water views of the Pond, Stonewall Beach and the Atlantic Ocean. You also have access to Stonewall Beach -- one of Chilmark's most prestigious private association beaches.... View all property information
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    5 of 5 stars Reviewed 27 December 2013
    we have stayed in this property 3 years running in both June and July. It's the most peaceful spot imaginable (no mobile phone signal) with unending wildlife activity ( we have...
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    $3,035
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    1 / 13
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Linens Provided
    • Microwave
    • Washer
    • Satellite TV
    • Dishwasher
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    About this property
    Located on the North side of Chilmark, this contemporary getaway offers a wide open living space with vaulted ceilings, stylish furnishings, a spacious deck and a stunning widow’s watch with water views. Completely renovated in 2012, this home feels like new and features a brand new kitchen with... View all property information
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    $5,039
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    1 / 10
    4 of 5 stars (1) Very good
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Deck
    • Dishwasher
    • Air Conditioning
    • Ceiling Fans
    • DVD Player
    • Satellite TV
    • Microwave
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
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    About this property
    Owner Transfer Ferry Tickets - Please Inquire Situated on a cul-de-sac overlooking a private meadow with spreading oaks ensures privacy. The screened porch, meadow bench, hammock and second floor deck off the master bedroom provide quiet spots to get away. Amenities and Features include...... View all property information
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    4 of 5 stars Reviewed 11 August 2014
    Great vacation. Home was clean, property is private and quiet and as always, very comfortable. Convenient location for our family vacation needs. Lack of recycling at house...
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    $4,856
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    1 / 22
    5 of 5 stars (1) Excellent
    4 Bedrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Internet Access
    • Microwave
    • Air Conditioning
    • Dishwasher
    • Stereo System
    • Satellite TV
    • Water Views
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    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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    5 of 5 stars Reviewed 3 September 2014
    Our family thoroughly enjoyed our week at the Mayhew home in Chilmark. We rented kayaks for some boating right off the private pier, picked clams, swam off the docked and cooked...
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    $3,035
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    1 / 22
    5 of 5 stars (1) Excellent
    4 Bedrooms / 5 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Fireplace
    • Washer
    • Water Views
    • Dryer
    • Grill
    • Deck
    • Stereo System
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    A boutique hotel experience in an unrivaled setting at the end of a one mile single lane road. Enjoy the sunrise from the ocean, sunset over the adjoining 13 acre Sheriff's Meadow Foundation conservation preserve. This home has a wonderful view toward Squibnocket Beach, a mile away, and the... View all property information
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    5 of 5 stars Reviewed 16 June 2014
    We stayed at this gorgeous home with a large family group in March. Fortunately for us, the weather was ideal. We had a lovely stay - everything at the house was wonderful and...
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    $3,460
    / Week
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    Amenities & Details
    • Deck
    • Air Conditioning
    • Dishwasher
    • Microwave
    • Patio
    • DVD Player
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Smoking allowed
    • Elder access
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    About this property
    Beautiful newly remodeled and newly furnished 4 bedroom home with private pool. Landscaping bordering the house and pool will be enhanced and ready for summer 2015, work to begin in April. Ten minute drive from the house to Menemsha village or Lucy Vincent beach. The house features a cook's kitchen... View all property information
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    $2,428
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    1 / 22
    Amenities & Details
    • Washer
    • TV
    • Stereo System
    • Deck
    • Porch
    • Dishwasher
    • DVD Player
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Located on Flanders Lane, this house sits up the hill and looks toward Menemsha. It is private and protected by the trees. Walk to watch sunsets in Menemsha or dine in one of the places to eat there or take in a day at the beach. Additional amenities include: beach chairs, dock/boat-slip, coffee... View all property information
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    $3,642
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    1 / 23
    Amenities & Details
    • Deck
    • Porch
    • DVD Player
    • Grill
    • Internet Access
    • Patio
    • TV
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Smoking allowed
    • Elder access
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    About this property
    Pine Ridge Farm sits peacefully tucked away on three acres of gently rolling meadows surrounded by stone walls. At the center of the compound is a classic Royal Barry Wills cape that has been smartly designed and finely appointed. An open Great Room with Living and Dining Areas has a two-story... View all property information
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    $11,534
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    1 / 16
    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Water Views
    • Deck
    • Washer
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • ?
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    About this property
    Beautiful, custom 4-bedroom house in an exclusive neighborhood with private association beach and tennis court. Spacious, comfortable living and dining room with cathedral ceilings, open to kitchen and upstairs loft with office. TV/sitting room nook off dining room. Expansive deck with stunning... View all property information
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    1 / 28
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Deck
    • Dishwasher
    • Linens Provided
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Smoking allowed
    • Elder access
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    About this property
    CHILMARK,Black Point Beach Heaven Sand Sun Surf and an immaculate house and guest quarters too................WOW This is not a fancy posh beach house. It is a wonderful relaxing, immaculate vacation destination for you and your family. You will find peace, ocean breezes, the sound of the surf,... View all property information
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    $7,892
    / Week
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    Amenities & Details
    • Water Views
    • Grill
    • Internet Access
    • Satellite TV
    • Deck
    • Dishwasher
    • Microwave
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Vacation in Chilmark on the pristine shores of the Tisbury Great Pond in this custom contemporary built with only the best materials. Four-bedroom main house with a detached guest suite. Open living/Dining/kitchen area with cathedral ceilings and exposed beams overlooking a luxurious setting by the... View all property information
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    $3,642
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    Amenities & Details
    • Deck
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Smoking allowed
    • Elder access
    • x
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    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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    $12,505
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    Amenities & Details
    • Deck
    • DVD Player
    • Grill
    • Microwave
    • Dishwasher
    • Satellite TV
    • Fireplace
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Through the private gate this home is set up on the hill with stunning views of Squibnocket Pond and the South Shore of the Atlantic. With endless windows to capture the natural surroundings and decks to enjoy the sun. 5 bedrooms and 5 baths allow the entire family their own space. An open kitchen... View all property information
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    From
    $2,125
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    Amenities & Details
    • Internet Access
    • Microwave
    • Deck
    • Grill
    • Dishwasher
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    A perfect up-island retreat - this charming two bedroom cottage has all that you could possibly imagine, nicely updated and comfort throughout. Enjoy Chilmark's famous beaches by day, relax on the screened porch with a book before dinner -- this is the meaning of rest and relaxation! Additional... View all property information
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    $15,176
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    Amenities & Details
    • Satellite TV
    • Stereo System
    • Microwave
    • Dishwasher
    • Grill
    • DVD Player
    • Water Views
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    SPECTACULAR and expansive views of the Vineyard Sound with 2-miles of private association beach to meander anytime your heart desires, lots of exploring or jumping from the infamous rock into the ocean below for the more adventuresome, all with Seven Gates tennis courts, trails and 2 Docks at your... View all property information
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    $24,282
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    Amenities & Details
    • Dishwasher
    • Grill
    • Deck
    • Air Conditioning
    • Fireplace
    • Internet Access
    • Satellite TV
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Stunning Chilmark rental home. This newly constructed contemporary home is situated high up from the water with fabulous views of the North Shore. There are numerous paths great for a hike or a run in the woods. Privacy, privacy, privacy. Great space in the main house with five bedrooms on the main... View all property information
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    $9,713
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    Amenities & Details
    • Stereo System
    • Washer
    • DVD Player
    • Grill
    • Air Conditioning
    • Dryer
    • Deck
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Smoking allowed
    • Elder access
    • x
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    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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    $9,106
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    1 / 17
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Satellite TV
    • Waterfront
    • Stereo System
    • Washer
    • Garage
    • Grill
    • Dryer
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
    • x
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    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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    $6,071
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    Amenities & Details
    • Washer
    • Dishwasher
    • Satellite TV
    • Deck
    • Dryer
    • Grill
    • Cooker
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Wonderful Vineyard cape situated on one of the most gorgeous spots on the island. The views are phenomenal in any direction and the house is cozy and charming. Large stretch of gorgeous, sandy and private beach. One of the most breathtaking spots on the island! Additional amenities include:... View all property information
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Patio
    • Stereo System
    • Washer
    • Grill
    • Satellite TV
    • Dryer
    • Fireplace
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Smoking allowed
    • Elder access
    • x
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    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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    1 / 27
    5 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Waterfront
    • Satellite TV
    • Cooker
    • Grill
    • DVD Player
    • Dryer
    • Washer
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Smoking allowed
    • Elder access
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    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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    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • DVD Player
    • Shared Outdoor Pool...
    • Stereo System
    • Satellite TV
    • Air Conditioning
    • Dryer
    • Cooker
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Smoking allowed
    • Elder access
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    About this property
    Breathtaking south shore ocean views from this pastoral setting await you. This striking contemporary has great spaces for everyone. Lovely furnishings and decor. All this and Chilmark beaches too. Additional amenities include: coffee maker, smoke free, lobster pot, 1st floor bedroom, 1 king... View all property information
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    Amenities & Details
    • DVD Player
    • Washer
    • Porch
    • Internet Access
    • Dryer
    • Waterfront
    • Deck
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
    • x
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    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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    Amenities & Details
    • Grill
    • Stereo System
    • Air Conditioning
    • Washer
    • Internet Access
    • Deck
    • Cooker
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Located in one of the most exclusive associations on the Vineyard, this five bedrooms home offers some of the most stunning water views the island has to offer. This home includes spacious decks, vaulted ceilings, and all the amenities one expects in a premier property. Tenants have access to both... View all property information
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    Amenities & Details
    • Grill
    • DVD Player
    • Internet Access
    • Dryer
    • Porch
    • Cooker
    • Satellite TV
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Spacious, contemporary Cape-style home with a wrap around deck tucked into a wooded hilllside on 3.8 acres. Distant waterviews of Cape Higon and Vineyard Sound. The overall design and layout with the 4 bedrooms and 2 lofts allows space for extended family get-togethers and special occasions.... View all property information
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    Amenities & Details
    • DVD Player
    • Deck
    • Linens Provided
    • Porch
    • Internet Access
    • Dryer
    • Grill
    • Cooker
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Smoking allowed
    • Elder access
    • x
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    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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    Amenities & Details
    • DVD Player
    • Fireplace
    • Washer
    • Linens Provided
    • Dryer
    • Deck
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Smoking allowed
    • Elder access
    • x
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    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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    $25,496
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    Amenities & Details
    • Washer
    • Satellite TV
    • Dryer
    • Grill
    • DVD Player
    • Stereo System
    • Cooker
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Exclusive Chilmark retreat perfectly blends casual elegance with stunning waterviews and a private pool. Enjoy the ocean-facing deck which provides a front row seat with plenty of room for entertaining and outdoor dining. A truly magical mix of a spectacular waterfront location, situated atop a... View all property information
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    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    Amenities & Details
    • Washer
    • Linens Provided
    • Deck
    • Dryer
    • Grill
    • Dishwasher
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Wonderful four bedroom home directly on Quitsa Pond with private deep water dock. One bedroom guest cottage included in rental. Additional amenities include: dock/boat-slip, smoke free, pets considered, lobster pot, 1st floor bedroom, 1 king bed(s), 8 dining capacity, 1 double bed(s), 4 single... View all property information
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    $5,949
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    Amenities & Details
    • Grill
    • DVD Player
    • Washer
    • Stereo System
    • Deck
    • Internet Access
    • Fireplace
    • Porch
    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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    5 Bedrooms / 4 Bathrooms / Sleeps 10
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    Amenities & Details
    • Dryer
    • Internet Access
    • Grill
    • Fireplace
    • Stereo System
    • Deck
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Squibnocket Farm is comprised of over 325 acres of beautiful rolling land nestled between Squibnocket Pond and the Atlantic Ocean. A very exclusive island location with only a few homes throughout the farm. Private access to a world-class beach and Squibnocket Pond - a rare combination of rural... View all property information
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    $9,106
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    Amenities & Details
    • Satellite TV
    • Porch
    • Grill
    • Washer
    • Stereo System
    • Internet Access
    • Deck
    • 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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    $18,212
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    Amenities & Details
    • Grill
    • Dryer
    • Washer
    • DVD Player
    • Deck
    • Air Conditioning
    • Patio
    • Fireplace
    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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    $9,713
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    5 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Dryer
    • Stereo System
    • Patio
    • Grill
    • Satellite TV
    • Internet Access
    • DVD Player
    • Deck
    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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    $3,035
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Deck
    • Cooker
    • Porch
    • Stereo System
    • DVD Player
    • Satellite TV
    • Linens Provided
    • Washer
    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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    $3,460
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    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • DVD Player
    • Fireplace
    • Dryer
    • Satellite TV
    • Porch
    • Internet Access
    • Stereo System
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Beautifully furnished and decorated home with all the amenities. Bright, airy two story interior, lovely views over Stonewall Pond to the barrier beach beyond, great sunsets via roof deck. Two story fireplace, recently renovated kitchen with all new appliances and granite tile counters. Complete... View all property information
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    $6,678
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    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Stereo System
    • Dishwasher
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    • 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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    $4,856
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    Amenities & Details
    • 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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    $7,892
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    Amenities & Details
    • 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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    $3,642
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    Amenities & Details
    • 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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    $7,285
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    Amenities & Details
    • Stereo System
    • Water Views
    • Dishwasher
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Wonderful, vintage Martha's Vineyard cottage. Simple living in Chilmark with modern conveniences. House offers four bedrooms with wonderful views over rolling meadow to Squibnocket Pond and Atlantic Ocean. Access to key beach in Gay Head. Additional amenities include: dock/boat-slip, house style:... View all property information
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    $9,106
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    Amenities & Details
    • Waterfront
    • Deck
    • Air Conditioning
    • Internet Access
    • Microwave
    • 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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    From
    $12,141
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    Amenities & Details
    • Internet Access
    • DVD Player
    • Water Views
    • Grill
    • Air Conditioning
    • Satellite TV
    • Dishwasher
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Stunning Chilmark property with wonderful privacy, peace and tranquility. This Martha's Vineyard vacation rental offers access to two keyed private association beaches Squibnocket Association and Long Beach, distant peak of a view to the Atlantic Ocean with classic Chilmark living and access to... View all property information
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