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Spectacular Home with Private Pool & Tennis 116946 - Chilmark vacation rentals
1 / 21

$1,143

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Spectacular Home with Private Pool & Tennis 116946

Chilmark house
4 BR / 3 BA / Sleeps 8 | Quick view

Details

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. Additional …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
Waterfront on Quitsa Pond with Dock 116754 - Chilmark vacation rentals
1 / 20

$1,429

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Waterfront on Quitsa Pond with Dock 116754

Chilmark house
4 BR / 3 BA / Sleeps 10 | Quick view

Details

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 bed(s), ironing board.
  • Waterfront
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Grill
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
Peaceful Setting Overlooking Meadow & Pond 116572 - Chilmark vacation rentals
1 / 27

$1,072

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Peaceful Setting Overlooking Meadow & Pond 116572

Chilmark house
3 BR / 3 BA / Sleeps 8 | Quick view

Details

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. Fully equipped kitchen…
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
Chilmark - Hillside retreat 119742 - Chilmark vacation rentals
1 / 12

$358

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Chilmark - Hillside retreat 119742

Chilmark house
4 BR / 3 BA / Sleeps 8 | Quick view

Details

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 top of the line …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Deck
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
#2081- Chilmark Rental w Lucy Vincent beach access - Chilmark vacation rentals
1 / 8

$300

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#2081- Chilmark Rental w Lucy Vincent beach access

Chilmark house
2 BR / Sleeps 4 | Quick view

Details

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 amenities include: …
  • Internet Access
  • Fireplace
  • Deck
  • Grill
  • Dishwasher
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
Peaceful Up-Island Classic with Waterviews 116670 - Chilmark vacation rentals
1 / 14

$572

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Peaceful Up-Island Classic with Waterviews 116670

Chilmark house
3 BR / 3 BA / Sleeps 6 | Quick view

Details

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 details. Additional …
  • Waterfront
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
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$1,472

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#2073 Stunning views of Squibnocket Pond and beyond

Chilmark house
5 BR / Sleeps 10 | Quick view

Details

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 living and dining …
  • Ocean or water views
  • Internet Access
  • Fireplace
  • A/C or climate control
  • Deck
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
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$1,472

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Chilmark - Stunning Waterviews in Squibnocket 116998

Chilmark house
5 BR / 5 BA / Sleeps 10 | Quick view

Details

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 the association and …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Deck
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 17

$286

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Waterview Cottage, Short Walk to Menemsha 116972

Chilmark house
3 BR / 2 BA / Sleeps 7 | Quick view

Details

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 pot, food processor, …
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 14

$929

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#2083 - Beautiful Chilmark Rental

Chilmark house
3 BR / Sleeps 6 | Quick view

Details

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 will start to relax…
  • Internet Access
  • Fireplace
  • A/C or climate control
  • Deck
  • Grill
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 11

$2,786

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Chilmark - 123611

Chilmark house
4 BR / 3 BA / Sleeps 10 | Quick view

Details

N/A
  • Waterfront
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 14

$643

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#2063 Enjoy access to a private beach & shared tennis court

Chilmark house
5 BR / Sleeps 10 | Quick view

Details

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 conservation land …
  • Ocean or water views
  • Internet Access
  • Deck
  • Dishwasher
  • Microwave
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
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$1,072

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#2062 A rare Chilmark find with spectacular ocean views

Chilmark house
5 BR / Sleeps 9 | Quick view

Details

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 with the ultimate …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Deck
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
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$429

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#2054 Lovely four bedroom home in Menemsha Hills

Chilmark house
4 BR / Sleeps 8 | Quick view

Details

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 hiking trails in …
  • Ocean or water views
  • Internet Access
  • Deck
  • Dishwasher
  • Microwave
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 10

$858

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#2047 Simple living in Chilmark with modern conveniences

Chilmark house
4 BR / Sleeps 6 | Quick view

Details

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: cape, bedding rm4: 2…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Deck
  • Dishwasher
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 9

$786

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#2014 Lovely Menemsha home with water views

Chilmark house
4 BR / Sleeps 9 | Quick view

Details

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 seating: 12, …
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Deck
  • Dishwasher
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 18

$929

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#2072 Sprawling house offers great space & more

Chilmark house
4 BR / Sleeps 7 | Quick view

Details

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 Turf surface and …
  • Internet Access
  • Deck
  • Grill
  • Dishwasher
  • Microwave
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
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$1,786

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2075

Chilmark house
5 BR / Sleeps 12 | Quick view

Details

N/A
  • Internet Access
  • Fireplace
  • Deck
  • Grill
  • Microwave
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 15

$429

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Spacious Contemporary in Wooded Hillside 114865

Chilmark house
4 BR / 4 BA / Sleeps 16 | Quick view

Details

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. Additional amenities …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Porch
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
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$972

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#2050 Private 7.2 acre compound with key to Quansoo Beach

Chilmark house
4 BR / Sleeps 8 | Quick view

Details

Located on 7.2 private acres in Chilmark, this 4500 sq. ft. home features a key to Quansoo beach, one of the most beautiful private association beaches on Martha's Vineyard Island. Professionally decorated with British West Indies style furnishings. Large gourmet kitchen includes a subzero refridgerator, wine chiller …
  • Internet Access
  • A/C or climate control
  • Deck
  • Dishwasher
  • Microwave
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 17

$715

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One Bedroom Located on Stonewall Beach 116924

Chilmark house
1 BR / 2 BA / Sleeps 2 | Quick view

Details

Ideally located on Stonewall Beach and Pond, panoramic water views. Open floor plan with lots of light, nicely furnished with gourmet kitchen and outdoor deck, perfect for entertaining. A great vacation home to unwind and enjoy the beauty of the Vineyard. Additional amenities include: dock/boat-slip, coffee maker, …
  • Waterfront
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 8

$258

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#2007 Quintessential Chilmark farm house on 12 acre estate

Chilmark house
4 BR / Sleeps 9 | Quick view

Details

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, security deposit: $…
  • Internet Access
  • Deck
  • Dishwasher
  • Microwave
  • Toaster
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
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$1,429

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#2061 Rental access to two keyed private association beaches

Chilmark house
4 BR / Sleeps 9 | Quick view

Details

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 hundreds of pristine …
  • Ocean or water views
  • Internet Access
  • Fireplace
  • A/C or climate control
  • Deck
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 26

$929

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Expansive Views of Farmland and Ocean 116399

Chilmark house
6 BR / 5 BA / Sleeps 8 | Quick view

Details

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 close to Chilmark …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Porch
  • Grill
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 27

$2,143

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High on a Hill, Walk to Squibnocket Beach 116957

Chilmark house
6 BR / 5 BA / Sleeps 8 | Quick view

Details

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 hardwood floors …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 23

$358

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Menemsha Sunsets, Harbor and Beach 113585

Chilmark house
4 BR / 3 BA / Sleeps 8 | Quick view

Details

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 porch. Guest cottage …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Porch
  • Grill
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 21

$715

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#2078 Incredible Chilmark Waterviews

Chilmark house
3 BR / Sleeps 8 | Quick view

Details

Chilmark waterview vacation rental. Driving down the wooded, rural road to this property you will see the grounds and water views open up to you as you approach. Wonderful yard with lots of space for afternoon picnics, lounging on the patio and cocktails in the evening after a great day on the beach. When entering the…
  • Ocean or water views
  • Fireplace
  • A/C or climate control
  • Deck
  • Grill
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 24

$3,000

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Exquisite Waterviews with Private Pool 116637

Chilmark house
5 BR / 4 BA / Sleeps 9 | Quick view

Details

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 hill with private …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 14

$2,858

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#2060 Situated high up from the water with fabulous views

Chilmark house
6 BR / Sleeps 12 | Quick view

Details

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 level and overflow …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 22

$858

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Waterfront Cottage with Menemsha Sunset 116499

Chilmark house
4 BR / 2 BA / Sleeps 6 | Quick view

Details

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 pot, 1st floor …
  • Waterfront
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 24

$2,572

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Spacious Cape Located on Chilmark Pond 116953

Chilmark house
4 BR / 4 BA / Sleeps 8 | Quick view

Details

Four bedroom contemporary Cape located directly on Chilmark Pond with desirable Hancock beach key. Tastefully decorated with all amenties including a cook s kitchen, pantry and laundry room adjacent to kitchen. Upstairs includes two bedrooms wtih bathrooms and sitting (tv) room with deck overlooking the pond. This …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 22

$786

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Top of the World Up-Island Hideaway 116377

Chilmark house
5 BR / 3 BA / Sleeps 7 | Quick view

Details

Spectacular retreat overlooking sweeping views of Menemsha, Elizabeth Islands, Gay Head Lighthouse and Aquinnah. Wonderfully furnished interior with special features and design throughout. Beautiful stone fireplace, open living area, fully equipped kitchen, perfect for entertaining. Master bedroom offers incredible …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 17

$1,072

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Breathtaking South Shore Ocean Views 116729

Chilmark house
4 BR / 3 BA / Sleeps 8 | Quick view

Details

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 bed(s), 1 queen bed(s…
  • Shared outdoor pool (unheated)
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 15

$572

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#2082 Tucked away in Chilmark full of peace and tranquility

Chilmark house
3 BR / Sleeps 8 | Quick view

Details

Tucked away in Chilmark full of peace, tranquility and privacy. This 3 bedroom 2 bathroom contemporary home offers plenty of space for indoor or outdoor living. As you dine on the back deck, there is a wonderful meadow to view and a hammock with your name on it. Indoor you will find all the amenities necessary to …
  • Internet Access
  • Fireplace
  • A/C or climate control
  • Deck
  • Grill
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 14

$500

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#2021 Sweeping water views of Quitsa, Menemsha Pond, & more

Chilmark house
4 BR / Sleeps 10 | Quick view

Details

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 with a ping pong room…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Deck
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 17

$715

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#2069 Stunning Chilmark property in Abel's Hill

Chilmark house
3 BR / Sleeps 6 | Quick view

Details

Stunning Chilmark property in Abel's Hill. Convenient location with great proximity to association beach and tennis, not far from Chilmark and West Tisbury town centers. Surrounded by open rolling hills with Japanese garden and fire pit, offering great privacy. Just steps to wonderful walking trails. Truly an …
  • Internet Access
  • A/C or climate control
  • Deck
  • Dishwasher
  • Microwave
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 10

$1,143

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Sweeping Waterviews, Great Sunsets - Spring Point 114884

Chilmark house
5 BR / 5 BA / Sleeps 10 | Quick view

Details

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, vaulted ceilings in great…
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Patio
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 24

$2,572

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Squibnocket Farm Beautiful Converted Barn 116303

Chilmark house
4 BR / 2 BA / Sleeps 7 | Quick view

Details

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 lofts overlook the …
  • Waterfront
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 21

$1,429

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#2064 This sprawling farm house is a found jewel

Chilmark house
5 BR / Sleeps 10 | Quick view

Details

This sprawling farm house which neighbors the Blue Heron Farm in Chilmark is a found jewel with fabulous views. The property offers five beautifully decorated bedrooms each with their own vineyard charm. Four being in the main house and a bunk room perfect for kids over the garage. Enjoy your family vacation sitting …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Deck
  • Dishwasher
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 27

$1,858

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Main & Guest House w/Quansoo Beach Access 114882

Chilmark house
5 BR / 5 BA / Sleeps 10 | Quick view

Details

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 just outside the door…
  • Waterfront
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 14

$715

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Chilmark - UpIsland Two Bedroom Guest Cottage 120760

Chilmark house
2 BR / 1 BA / Sleeps 8 | Quick view

Details

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 capacity, lobster …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 7

$2,858

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#2038 Spectacular Chilmark home overlooking Lucy Vincent

Chilmark house
5 BR / Sleeps 10 | Quick view

Details

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 amenities include: add …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Deck
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 30

$4,000

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#2080 Tranquil and extremely private setting in Chilmark

Chilmark house
6 BR / Sleeps 13 | Quick view

Details

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 and outdoor splendor…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
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$286

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#2084 - Lovely Chilmark Cottage for rent

Chilmark house
2 BR / Sleeps 4 | Quick view

Details

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 cottage and kick back and…
  • Internet Access
  • A/C or climate control
  • Deck
  • Grill
  • Dishwasher
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
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$286

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#2071 A very special Windy Gates offering

Chilmark house
4 BR / Sleeps 8 | Quick view

Details

A very special Windy Gates offering. Four bedroom converted barn offers a large open first floor with kitchen, dining and living space. Great barn doors open to patio seating outside. Four bedrooms upstairs with one hall bath and a second bath at the bottom of the stairs. Enjoy this Martha's Vineyard vacation rental …
  • Internet Access
  • Deck
  • Grill
  • Dishwasher
  • Microwave
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
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$715

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Sweeping Views of Elizabethan Islands 116586

Chilmark house
4 BR / 4 BA / Sleeps 9 | Quick view

Details

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 - living, dining and …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
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$700

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Spacious Five Bedroom with Sweeping Views 116752

Chilmark house
5 BR / 5 BA / Sleeps 9 | Quick view

Details

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 an amazing yard. …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
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$358

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Elegant Waterfront Beach House Retreat 116330

Chilmark house
4 BR / 5 BA / Sleeps 8 | Quick view

Details

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 s/week, …
  • Waterfront
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
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$1,143

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#2001 3+ acres overlooking the Elizabeth Islands & beyond

Chilmark house
4 BR / Sleeps 10 | Quick view

Details

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 activities such as …
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Deck
  • Grill
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
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$179

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Menemsha Sunsets on the Deck 116552

Chilmark house
2 BR / 1 BA / Sleeps 4 | Quick view

Details

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 trundle(s), vacuum cleaner, …
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
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