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$929

5 BR / 0 BA / Sleeps 10

#2057 Elegance & style in private setting w/ key to Quansoo - Chilmark vacation rentals
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$929

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#2057 Elegance & style in private setting w/ key to Quansoo

Chilmark house
5 BR / Sleeps 10 | Quick view

Details

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 fireplace. Separate…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Deck
  • Grill
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$4,000

6 BR / 0 BA / Sleeps 13

#2080 Tranquil and extremely private setting in Chilmark - Chilmark vacation rentals
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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$1,029

4 BR / 3 BA / Sleeps 8

HERGT - Luxury Retreat, Ferry Tickets,  Quansoo Association Beach Rights, Central Air, 4500 sq. ft. - Chilmark vacation rentals
1 / 30

Details

Outstanding private rental home nestled on 7.2 private acres in the seaside community of Chilmark on the Island of Martha's Vineyard, features a key to Quansoo Beach, one of the most beautiful private association beaches on the island. Warmth, comfort and charm await you and your family in this air conditioned, 4500 …
  • Phone / Internet
  • A/C or climate control
  • Porch
  • Grill
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$150

4 BR / 2 BA / Sleeps 9

Chilmark Contemporary Cape with Access to Beaches 116588 - Chilmark vacation rentals
1 / 10

$150

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Chilmark Contemporary Cape with Access to Beaches 116588

Chilmark house
4 BR / 2 BA / Sleeps 9 | Quick view

Details

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 access to Chilmark …
  • 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

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$1,786

7 BR / 0 BA / Sleeps 10

#2079 SPECTACULAR and expansive views of the Vineyard Sound - Chilmark vacation rentals
1 / 26

$1,786

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#2079 SPECTACULAR and expansive views of the Vineyard Sound

Chilmark house
7 BR / Sleeps 10 | Quick view

Details

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 fingertips. Inside …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Deck
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$643

4 BR / 3 BA / Sleeps 8

1505 - ENJOY OCEAN VIEWS FROM THIS CHILMARK HOME - Chilmark vacation rentals
1 / 7

$643

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1505 - ENJOY OCEAN VIEWS FROM THIS CHILMARK HOME

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

Details

Unique combination of 1940's camp-style home and new (2007) two-story addition. Beautiful Ocean views from all floors, two decks, two living rooms and wonderful prevailing SW breezes. Five minute walk to Ocean Beach adjacent to Lucy Vincent Beach. Access to private Able's Hill Association beach and 3 tennis courts. …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Patio
  • Smoking allowed - ask
  • Suitable for children - over five
  • Suitable for the elderly - ask

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$715

3 BR / 0 BA / Sleeps 8

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

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$736

5 BR / 4 BA / Sleeps 8

1 / 31

$736

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MICHA - Chilmark Hilltop Luxury Home, A/C, Wifi Internet

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

Details

MVVR EXCLUSIVE: Spectacular 5 bedroom, 4.5 bath retreat. Lovely distant waterviews overlooking the South Shore. Hilltop setting with privacy and a five minute drive to Lucy Vincent Beach. This spacious custom home has been decorated by one of the island's premier professionals. A combination of contemporary …
  • Ocean or water views
  • Phone / Internet
  • A/C or climate control
  • Porch
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$358

3 BR / 2 BA / Sleeps 6

1 / 16

Details

This newly remodeled 3 bedroom 2 bath has a spacious master bedroom suite, cozy sun room and updated kitchen. It has a great yard with garden landscaping, a perfect spot for outdoor dining. 1.5 miles from Alley's store. 3.3 miles to Lucy Vincent Beach.The bathrooms are fully remodeled. An easy, comfortable house in a …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$150

4 BR / 2 BA / Sleeps 8

1 / 11

Details

Immaculate 4 bedroom in a private setting yet just a 10 minute drive to town or the most beautiful Lucy Vincent Beach. Features include large deck and wifi internet. The house has an open floor plan and an additional family/tv room for your comfort. Amenities and Features include... Large Deck, Wifi, A/C, …
  • Internet Access
  • A/C or climate control
  • Deck
  • Grill
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$572

3 BR / 2 BA / Sleeps 6

1 / 23

$572

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DIETR - Menemsha Pond Waterfront, Mooring, Wifi, Central A/C

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

Details

Steps from Menemsha Pond – look across the ever-changing surface of the water to Menemsha, the Creek, the Lobsterville dunes, Vineyard Sound and the Elizabeth Islands. Magnificent sunsets from the living room. This cathedral-ceiling Modernist masterpiece is constructed entirely of Western red cedar. Central air and …
  • Waterfront
  • Ocean or water views
  • Phone / Internet
  • A/C or climate control
  • Deck
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$486

4 BR / 2 BA / Sleeps 8

1 / 25

$486

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KOGAB - Chilmark, South Road, 3 Miles to Lucy Vincent Beach, WiFi

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

Details

Tastefully furnished and decorated with antiques and art. This Chilmark summer home is an original Yankee Barn located off South Road that has all the accouterments for summer entertaining. The post and beam structure features a beautiful cathedral living room brightened by southern light; has sliders out to a wrap-…
  • Phone / Internet
  • Deck
  • Grill
  • Dishwasher
  • Microwave
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$358

4 BR / 3 BA / Sleeps 8

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

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$286

2 BR / 0 BA / Sleeps 4

1 / 8

$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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$1,358

4 BR / 3 BA / Sleeps 8

1 / 16

$1,358

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1675 - Spectacular Home with Waterviews of Vineyard Sound and Elizabeth Islands

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

Details

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 north shore water views…
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Smoking allowed - ask
  • Suitable for children - over five
  • Suitable for the elderly - ask

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$1,786

7 BR / 4 BA / Sleeps 9

1 / 31

$1,786

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SEVEN GATES FARM WATERFRONT: CLASSIC CHILMARK CAPE - CHIL CFUL-35

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

Details

Serenely tucked away on the rolling hills and meadows of prestigious Seven Gates Farm, this Classic Chilmark home sits directly on the north shore with stunning water views of Vineyard Sound and the Elizabeth Islands, with its own curving coastline of Seven Gates beach. There is vintage charm throughout this seven …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Patio
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$636

4 BR / 3 BA / Sleeps 8

1 / 18

Details

Panoramic South Shore ocean vista from this outstanding private rental home. Less than one mile to famous Lucy Vincent Beach. Owner also offers private beach rights to the south side via canoe or kayak (provided by owners.) Classic style and modern luxury combine to make this family retreat a very special rental. Part…
  • Private Beach
  • Ocean or water views
  • Phone / Internet
  • A/C or climate control
  • Porch
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$736

1 BR / 2 BA / Sleeps 3

1 / 14

$736

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YEOM1 - Waterview, Walk to Private Association South Shore Beach

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

Details

"The Little House" on the beach. Two minute stroll to South surf beach. Incredible views from sunrise to sunset. Private tennis courts shared with owners and other tenants. Access to Stonewall Pond for launching canoes and kayaks. This wonderful cottage is a one of a kind. A pet will be considered on a case by case …
  • Waterfront
  • Ocean or water views
  • Phone / Internet
  • Porch
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,472

5 BR / 5 BA / Sleeps 10

1 / 40

$1,472

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THE ROOST AT SQUIBNOCKET FARM - CHIL RHOR-17

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

Details

Aptly named for its stunning perch in prestigious Squibnocket Farm on the shores of Squibnocket Pond, The Roost features panoramic water views that stretch from the far southwestern shoreline of Martha's Vineyard, across Chilmark's Squibnocket and Stonewall Beaches, and continue along the Island's entire south shore …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$429

4 BR / 3 BA / Sleeps 8

1 / 24

$429

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LENOM HOUSE AT STONEWALL POND - CHIL RALD-138A

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

Details

Enjoy sweeping water views across Stonewall Pond and Beach, as well as access to the private ocean beach at prestigious Stonewall Beach. Lenom House is tucked away between Stonewall and Quitsa Ponds, with dramatic water views of both well known Chilmark Ponds, plus the south shore and Stonewall Beach. The open first …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$358

4 BR / 4 BA / Sleeps 8

1 / 23

$358

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JAFFJ - Oceanfront, Waterview, Private Beach and Tennis

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

Details

Ocean Front Splendor in an elegant and comfortable beach house. Sunrise from the ocean, sunset over the adjoining 13-acre Sheriff's Meadow Foundation conservation preserve. Walk to your private beach. New 500 square foot addition, added for summer 2008, includes ground floor Master Bedroom suite, with separate …
  • Private Beach
  • Waterfront
  • Ocean or water views
  • Phone / Internet
  • Deck
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,786

5 BR / 5 BA / Sleeps 10

1 / 16

Details

Newly constructed home has open concept living area with 270 degree water views, abundant natural sunlight, central AC, high end appliances, hardwood floors, rooftop deck with seating to view gorgeous island sunsets, access to several private beaches,and high speed internet wifi. Additional amenities include: beach …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$358

3 BR / 3 BA / Sleeps 6

1 / 17

$358

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Breathtaking Views, Private Beach and Tennis 116922

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

Details

Breathtaking views of the Atlantic ocean, Stonewall Pond, Squibnocket and Nomans Land Island. Home sits on six acres, with private beach and newly resurfaced tennis court. Beautiful up-island getaway. Additional amenities include: coffee maker, smoke free, pets considered, lobster pot, food processor, 1st floor …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Grill
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$383

3 BR / 3 BA / Sleeps 6

1 / 18

$383

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ITALA - North Slope Custom Home, Large Wrap Around Deck, WiFi

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

Details

Contemporary Post and Beam home, private location, bounded by large oaks and stone walls. Enjoy this impeccably maintained 3 bedroom, 3 bath home. Custom designed and featuring a chef's kitchen. The cathedral ceiling great room is open to the spacious dining and kitchen area. Custom features include exposed wood beams…
  • Internet Access
  • Deck
  • Grill
  • Dishwasher
  • Microwave
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$358

4 BR / 4 BA / Sleeps 16

1 / 15

$358

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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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$1,472

5 BR / 5 BA / Sleeps 10

1 / 27

$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

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$1,472

5 BR / 0 BA / Sleeps 10

1 / 35

$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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$1,072

5 BR / 0 BA / Sleeps 9

1 / 28

$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

PreviousNext property

$572

3 BR / 3 BA / Sleeps 6

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

PreviousNext property

$429

5 BR / 2 BA / Sleeps 9

1 / 19

$429

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Spacious Menemsha Waterview Rental (Spacious-Menemsha-Waterview-Rental-CH203)

Chilmark house
5 BR / 2 BA / Sleeps 9 | Quick view

Details

Reverse Contemporary Five Bedroom home just minutes to Menemsha. There are open living spaces with living room , dining room and kitchen that open to deck with waterviews of the North Shore. Just a short drive to famous Lucy Vincent Beach, Chilmark Store, library and Community Center. Walk to a Menemsha Beach on a …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$215

2 BR / 1 BA / Sleeps 4

1 / 8

$215

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JAFFP - Waterfront Guest House, Private Beach

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

Details

Main House on the same property may be occupied by Owner or another Tenant. Peaceful private setting on one of the most beautiful areas on the South Shore. Amenities and Features include... Waterfront Guest House, Private Beach Additional amenities include: coffee maker, internet - ethernet cord required, fans - …
  • Private Beach
  • Waterfront
  • Ocean or water views
  • Phone / Internet
  • Patio
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$858

6 BR / 2 BA / Sleeps 11

1 / 35

Details

Style, warmth, and comfort define this delightful farm house in Menemsha with a water view to the Vineyard Sound. The property is spacious and private. There is a tennis court shared by the occupants of the neighboring barn. The house comes with a key to a beach in Aquinnah on Moshup trail and a shared key to Quansoo …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$229

1 BR / 1 BA / Sleeps 4

1 / 14

$229

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Menemsha Dream Cottage Overlooking Harbor 114931

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

Details

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 awaits you in this …
  • Waterfront
  • Deck
  • Linens Provided
  • Microwave
  • Stove or Oven
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$786

5 BR / 3 BA / Sleeps 7

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

PreviousNext property

$358

3 BR / 2 BA / Sleeps 6

1 / 14

$358

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Cozy, Charming Three Bedroom Cape 116554

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

Details

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 include: coffee maker, …
  • 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

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$929

4 BR / 0 BA / Sleeps 8

1 / 25

$929

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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

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$543

4 BR / 3 BA / Sleeps 6

1 / 29

Details

This incredible home is furnished with one of a kind artisan wood and textile pieces, as well as Donghia soft seating and is filled with art, vintage stain glass, antiques, and one of kind artisan furniture. The ocean view is spectacular from the great room (living room, dining area and kitchen, two bedrooms (master …
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Deck
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$1,072

3 BR / 3 BA / Sleeps 8

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

PreviousNext property

$454

4 BR / 2 BA / Sleeps 6

1 / 24

$454

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LEWDG - Waterfront, Waterview, Walk to Beach, Hi Speed Internet, WiFi

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

Details

Casual immaculately clean in picturesque Menemsha, Chilmark waterfront. Beautiful views. A short stroll to the beach, fish market, boutiques, fishing, and shore dinners. Guest House - Main House on property nearby may be occupied by Tenants or Owner. Amenities and Features include... Waterfront, Waterview, Walk to…
  • Waterfront
  • Ocean or water views
  • Phone / Internet
  • Deck
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$715

5 BR / 3 BA / Sleeps 9

1 / 19

$715

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Bluff House, Waterfront with Private Beach 114875

Chilmark house
5 BR / 3 BA / Sleeps 9 | Quick view

Details

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: dock/boat-slip, coffee …
  • 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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$518

3 BR / 2 BA / Sleeps 8

1 / 24

Details

Owner Transfer Ferry Tickets - Please Inquire Stunning Waterfront Views. Kayak or swim across the pond to Stonewall Beach or just relax on the expansive decks overlooking the water. This is an immaculate older home, very comfortably furnished with 3 bedrooms and 2 baths. High Speed Internet. Renters can tie their …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Deck
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$179

2 BR / 1 BA / Sleeps 4

1 / 9

$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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$929

6 BR / 5 BA / Sleeps 8

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

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$358

4 BR / 3 BA / Sleeps 8

1 / 28

$358

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STRAA

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

Details

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, star filled skies, moon…
  • Internet Access
  • Patio
  • Grill
  • Linens Provided
  • Dishwasher
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$358

1 BR / 1 BA / Sleeps 4

1 / 17

$358

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Private Boathouse at Edge of Stonewall Pond 116925

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

Details

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: dock/boat-slip, …
  • Waterfront
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Porch
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$2,858

5 BR / 0 BA / Sleeps 10

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

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$279

3 BR / 2 BA / Sleeps 6

1 / 15

$279

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PERRG - A/C, WiFi

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

Details

Amenities and Features include... A/C, WiFi Additional amenities include: coffee maker, patio table and chairs, fans - portable, lobster pot, washer / dryer, cd player, landscaped, porch - screened, outside shower - enclosed, vacuum, outdoor furniture, ironing board.
  • Phone / Internet
  • A/C or climate control
  • Patio
  • Grill
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$858

4 BR / 0 BA / Sleeps 6

1 / 10

$858

Inquire

#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

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$1,143

5 BR / 5 BA / Sleeps 10

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

PreviousNext property

$358

4 BR / 3 BA / Sleeps 8

1 / 38

$358

Inquire

Lovely Beach Cottage In Menemsha! (Lovely-Beach-Cottage-In-Menemsha!-CH226)

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

Details

This quintessential beach house offers proximity to Menemsha while being removed from traffic and the hustle and bustle. It comes with an updated and well equipped kitchen for dining delights with the fresh fish just around the corner. A screen porch looking out over the view. The perfect seat for spectacular sunsets…
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
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