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$500

4 BR / 0 BA / Sleeps 10

#2021 Sweeping water views of Quitsa, Menemsha Pond, & more - Chilmark vacation rentals
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$500

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

4 BR / Sleeps 10 | Quick view

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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

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$1,143

4 BR / 0 BA / Sleeps 10

#2001  3+ acres overlooking the Elizabeth Islands & beyond - Chilmark vacation rentals
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$1,143

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#2001 3+ acres overlooking the Elizabeth Islands & beyond

4 BR / Sleeps 10 | Quick view

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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
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  • Wheelchair accessible - ask

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$558

3 BR / 0 BA / Sleeps 8

#2082 Tucked away in Chilmark full of peace and tranquility - Chilmark vacation rentals
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$558

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#2082 Tucked away in Chilmark full of peace and tranquility

3 BR / Sleeps 8 | Quick view

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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 …
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  • Pet friendly - ask
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$250

2 BR / 0 BA / Sleeps 4

#2081- Chilmark Rental w Lucy Vincent beach access - Chilmark vacation rentals
1 / 8

$250

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#2081- Chilmark Rental w Lucy Vincent beach access

2 BR / Sleeps 4 | Quick view

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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
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  • Deck
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  • Dishwasher
  • Pet friendly - 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
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$1,786

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#2079 SPECTACULAR and expansive views of the Vineyard Sound

7 BR / Sleeps 10 | Quick view

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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
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  • Internet Access
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  • Pet friendly - ask
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$929

3 BR / 0 BA / Sleeps 6

#2083 - Beautiful Chilmark Rental - Chilmark vacation rentals
1 / 14

$929

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#2083 - Beautiful Chilmark Rental

3 BR / Sleeps 6 | Quick view

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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
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  • Deck
  • Grill
  • Pet friendly - 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

5 BR / Sleeps 10 | Quick view

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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
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  • Wheelchair accessible - ask

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$715

3 BR / 0 BA / Sleeps 8

1 / 21

$715

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#2078 Incredible Chilmark Waterviews

3 BR / Sleeps 8 | Quick view

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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
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$215

2 BR / 0 BA / Sleeps 5

1 / 9

$215

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#2006 Post & beam vacation home in a lovely rural setting

2 BR / Sleeps 5 | Quick view

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Post and Beam Martha's Vineyard vacation rental in a lovely rural setting in Chilmark. Two bedrooms with large decks and distant waterview of Lucy Vincent beach. Additional amenities include: wood stove, television: regular, outdoor shower: enclosed, check in time: 2:00, flipkey header: #2006 post & beam vacation …
  • Ocean or water views
  • Deck
  • Grill
  • Dishwasher
  • Microwave
  • Pet friendly - ask
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$715

3 BR / 0 BA / Sleeps 6

1 / 17

$715

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#2069 Stunning Chilmark property in Abel's Hill

3 BR / Sleeps 6 | Quick view

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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
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  • Deck
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  • Microwave
  • Pet friendly - ask
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  • Wheelchair accessible - ask

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$643

3 BR / 2 BA / Sleeps 6

1 / 18

$643

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WILGG - Quansoo (with private beach key), Central Air, Waterview, Waterfront

3 BR / 2 BA / Sleeps 6 | Quick view

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Amenities and Features include... Quansoo (with private beach key), Central Air, Waterview, Waterfront Additional amenities include: coffee maker, internet - ethernet cord required, pets considered, lobster pot, washer / dryer, cd player, porch - screened, outside shower - enclosed, private beach - association, …
  • Waterfront
  • Ocean or water views
  • Phone / Internet
  • A/C or climate control
  • Deck
  • Suitable for children - ask
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  • Wheelchair accessible - ask

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$429

5 BR / 2 BA / Sleeps 9

1 / 19

$429

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

5 BR / 2 BA / Sleeps 9 | Quick view

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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
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  • Deck
  • Grill
  • Suitable for children - ask
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$358

4 BR / 3 BA / Sleeps 8

1 / 23

$358

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Menemsha Sunsets, Harbor and Beach 113585

4 BR / 3 BA / Sleeps 8 | Quick view

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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 …
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$1,143

4 BR / 2 BA / Sleeps 2

1 / 24

Details

Located in Menemsha down a dirt road to privacy and serenity, this house is constructed carefully and artfully. The space is light filled with cathedral ceilings in the living area grounded by a hand built fireplace. All decorations and objects have been carefully picked to accent the space with comfort and harmony. …
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  • Suitable for children - ask
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$286

4 BR / 0 BA / Sleeps 8

1 / 13

$286

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#2071 A very special Windy Gates offering

4 BR / Sleeps 8 | Quick view

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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
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  • Microwave
  • Pet friendly - ask
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$786

5 BR / 3 BA / Sleeps 10

1 / 19

Details

This colorful and spacious home has room for a large family or a smaller one with guests. On breezy days, lounge in the sun on the back deck protected from the wind. Take in the sunsets from the back deck, sunrises from the kitchen deck. The house comes with boogie boards and beach toys, beach chairs, chaises lounges…
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Grill
  • Suitable for children - ask
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  • Wheelchair accessible - ask

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$686

3 BR / 2 BA / Sleeps 6

1 / 27

Details

This house is set in a pastoral surrounding. It has beautifully tended grounds with a Peter Rabbit enclosed flower garden and rolling lawns. The well equipped gourmet kitchen overlooks the dining and living rooms. There is a four season porch off the living room and a sun bathed deck. The downstairs features a media …
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$572

5 BR / 0 BA / Sleeps 10

1 / 14

$572

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

5 BR / Sleeps 10 | Quick view

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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

5 BR / 0 BA / Sleeps 9

1 / 28

$1,072

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#2062 A rare Chilmark find with spectacular ocean views

5 BR / Sleeps 9 | Quick view

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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
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$1,429

4 BR / 0 BA / Sleeps 9

1 / 26

$1,429

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#2061 Rental access to two keyed private association beaches

4 BR / Sleeps 9 | Quick view

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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

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$429

4 BR / 0 BA / Sleeps 8

1 / 13

$429

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#2054 Lovely four bedroom home in Menemsha Hills

4 BR / Sleeps 8 | Quick view

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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

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$858

4 BR / 0 BA / Sleeps 6

1 / 10

$858

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#2047 Simple living in Chilmark with modern conveniences

4 BR / Sleeps 6 | Quick view

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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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$786

4 BR / 0 BA / Sleeps 9

1 / 9

$786

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#2014 Lovely Menemsha home with water views

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

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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

5 BR / Sleeps 10 | Quick view

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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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$1,786

5 BR / 0 BA / Sleeps 12

1 / 26

$1,786

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2075

5 BR / Sleeps 12 | Quick view

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N/A
  • Internet Access
  • Fireplace
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  • Pet friendly - ask
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$929

4 BR / 0 BA / Sleeps 7

1 / 18

$929

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#2072 Sprawling house offers great space & more

4 BR / Sleeps 7 | Quick view

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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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$258

4 BR / 0 BA / Sleeps 9

1 / 8

$258

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#2007 Quintessential Chilmark farm house on 12 acre estate

4 BR / Sleeps 9 | Quick view

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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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$893

4 BR / 3 BA / Sleeps 8

1 / 23

Details

Sit on the porch of this fabulous four bedroom home and take in the panoramic water views. Enjoy watching the sheep grazing around the property which is part of a working farm. Access a gorgeous south shore private beach by canoe or kayak. The home is private, comfortable and convenient to the Chilmark Community …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,000

6 BR / 4 BA / Sleeps 10

1 / 18

Details

This gracious Vineyard elongated Cape overlooks the Keith Farm and the Atlantic Ocean beyond. The gourmet kitchen has just been beautifully renovated and is a dream. The living areas are all decorated with charm and all have views. The separate main house, with four bedrooms, and guest house, with two bedrooms, allow …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Porch
  • Suitable for children - ask
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  • Wheelchair accessible - ask

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$475

6 BR / 2 BA / Sleeps 14

1 / 20

Details

A large rambling old family home where memories are made. The extended family can all join in a vacation full of laughter and play. The grounds are full of places for hide-and-go-seek. Privately set on Middle Road in the woods yet bathed in sunlight. The house has a string of bedrooms for all the family members to …
  • Internet Access
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  • Deck
  • Grill
  • Suitable for children - ask
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  • Wheelchair accessible - ask

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$643

5 BR / 4 BA / Sleeps 9

6 Reviews

$643

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Stunning Multi-Generational 5 BR Ocean View Home!

5 BR / 4 BA / Sleeps 9 | Quick view
“ Excellent ” 6 Reviews

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Reviews

(6)

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 sunshine and …
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(6)

Peaceful Beauty

Left on Jun 14, 2010 for a stay in May 2009

This home sits serenely on a small hill surrounded by fields. The floor plan is open and airy, with sunlight filling the rooms. Furnishings are comfortable. I especially love the gourmet kitchen and the view of the ocean from the living room. The lower level sleeping area is perfect for the kids, with the two master bedrooms on the main floor nice sized. The house is well appointed and organized…

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$3,750

4 BR / 3 BA / Sleeps 8

1 / 20

$3,750

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4 Bedroom on 5 Acres of Woodlands with Fresh Eggs and Chickens

4 BR / 3 BA / Sleeps 8 | Quick view

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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 contained in very …
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask

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$228

2 BR / 1 BA / Sleeps 3

1 / 12

$228

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MARTHA’S VINEYARD - AUGUST. Menemsha, Chilmark

2 BR / 1 BA / Sleeps 3 | Quick view

Details

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, 1 child. No pets. …
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Books
  • Grill
  • Suitable for children - ask

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$358

4 BR / 4 BA / Sleeps 8

1 / 21

$358

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CHILMARK RETREAT: MODERN STYLING, PRIVATE SETTING - CHIL MMAD-20

4 BR / 4 BA / Sleeps 8 | Quick view

Details

Privately tucked away in the rolling hills of the historic Tea Lane area, surrounded by conservation land, the newly renovated Chilmark Retreat features a sleek modern style, with a sunny, open floor plan. There are sharp designer touches throughout, mixed with monochromatic shades of white and other muted tones, from…
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Porch
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$572

4 BR / 3 BA / Sleeps 8

1 / 22

$572

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HILLTOP HOUSE WITH DISTANT WATER VIEWS - CHIL AMOS-95

4 BR / 3 BA / Sleeps 8 | Quick view

Details

Sitting high atop a ridge in Chilmark, the distant ocean views from Hilltop House stretch as far as Woods Hole and the Elizabeth Islands to Menemsha. The three-acre hillside setting is both spectacular and private. The recently renovated house has two walls of glass sliding doors that frame the Living Area and Kitchen…
  • Internet Access
  • Washing Machine
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  • Porch
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$345

3 BR / 3 BA / Sleeps 6

1 Reviews

$345

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Charming Chilmark 3 Bedroom 3 Bath Vacation Home

3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Located in Chilmark on Martha's Vineyard, this 3 bedroom, 3 bathroom property is a perfect spring, summer or fall getaway. Cathedral ceilings create bright, airy spaces. Amenities include air conditioning, high speed internet, washer/dryer, gas fireplaces, TV in all rooms, outdoor shower, slate patio and beautifully …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Great house for the price

Left on Sep 12, 2013 for a stay in August 2013

This house is an unexpected surprise. it is very well equipped and was perfect for two couples for the week and a teenager who spent the weekend. Everyone had their privacy, and the house pulled us to congregate outside on the deck and patio overlooking a charming garden. For those who don't need excessive luxury, but want a pleasant setting that is easily accessible to up island and down, and …

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$786

3 BR / 3 BA / Sleeps 6

1 / 23

$786

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THE MEADOW FARMHOUSE AT MENEMSHA POND - CHIL LMCC-23

3 BR / 3 BA / Sleeps 6 | Quick view

Details

This historic farmhouse is quietly tucked away above Menemsha Pond with sweeping sunset and water views of The Pond and Menemsha Harbor. The tranquil setting is classic Chilmark with rolling hills and stonewalls, plus a private association beach just a short stroll away on Menemsha Pond. Three-hundred year old Meadow …
  • 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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$429

5 BR / 3 BA / Sleeps 9

1 / 26

$429

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CONTEMPORARY ARTIST RETREAT ON SQUIBNOCKET POND - CHIL WWEL-19

5 BR / 3 BA / Sleeps 9 | Quick view

Details

The ultimate artist or family retreat tucked away amid the rolling hills and stonewalls of Squibnocket Pond in Chilmark. The panoramic water views look out across the Pond, the barrier beach and sand dunes of the Island's southwestern most point, and on out to No Man's Island and the Atlantic Ocean. Built by a …
  • 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

5 BR / 3 BA / Sleeps 10

1 / 21

$429

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SUNSET FARM ON SQUIBNOCKET POND WITH SWEEPING WATER VIEWS - CHIL WWEL-18

5 BR / 3 BA / Sleeps 10 | Quick view

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Privately tucked away on 20 acres of rolling hills and meadows that run along the shoreline of Squibnocket Pond, this mission-style home enjoys stunning sunset and water views across the Pond, the sand dunes of the Island's most southwestern point, and on across the Atlantic Ocean out to No Man's Island. The house is …
  • 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 10

1 / 23

$429

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PINE RIDGE FARM: COUNTRY CAPE WITH GUEST COTTAGE - CHIL EHIN-05

4 BR / 3 BA / Sleeps 10 | Quick view

Details

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 vaulted ceiling and a …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Porch
  • Grill
  • Pet friendly - ask
  • Smoking allowed - 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 / 40

$1,472

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THE ROOST AT SQUIBNOCKET FARM - CHIL RHOR-17

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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$1,786

5 BR / 5 BA / Sleeps 10

1 / 29

$1,786

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QUANSOO WATERFRONT COMPOUND WITH GUEST COTTAGE - CHIL EBRA-61

5 BR / 5 BA / Sleeps 10 | Quick view

Details

Tucked away in the prestigious Quansoo area of Chilmark, this architect-designed compound sits peacefully on the shores of the Tisbury Great Pond. There are sophisticated touches inside and out, with a Main House, Guest House, and key access to Quansoo Beach. The Main House is centered around a two-story Great Room …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Porch
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$2,858

6 BR / 6 BA / Sleeps 12

1 / 28

$2,858

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VISTA POINT: STUNNING ARCHITECTURAL DESIGN ON THE NORTH SHORE - CHIL DROT-69

6 BR / 6 BA / Sleeps 12 | Quick view

Details

Vista Point combines a truly magical mix of a spectacular, waterfront location, with equaling stunning architectural design. Sitting high atop a north shore ridge in Chilmark, the views stretch west from the Aquinnah cliffs and lighthouse, north to the Elizabeth Islands, and east toward Lambert's Cove Beach. Drawing …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Porch
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - 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

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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$150

4 BR / 2 BA / Sleeps 8

1 / 13

$150

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714 - SPACIOUS AND COMFORTABLE CHILMARK CAPE WITH CENTRAL AIR CONDITIONING

4 BR / 2 BA / Sleeps 8 | Quick view

Details

This spacious and comfortably furnished contemporary Cape is conveniently located between Chilmark and West Tisbury. The master bedroom and bath are downstairs; three bedrooms and a bath are upstairs off the loft that overlooks the living and dining rooms. The living and dining rooms have a cathedral ceiling, wood …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Porch
  • Smoking allowed - ask
  • Suitable for children - over five
  • Suitable for the elderly - ask

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$143

2 BR / 2 BA / Sleeps 4

1 / 11

$143

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329 - CHARMING WATERFRONT COTTAGE WITH WONDERFUL VIEWS OF THE ATLANTIC OCEAN

2 BR / 2 BA / Sleeps 4 | Quick view

Details

The Pond House, located on Stonewall beach in Chilmark, is a charming cottage is situated on the edge of the rolling lawns of the main house. The beauty and serenity experienced here are what the Vineyard is all about; Stonewall Pond to the west, the Atlantic to the southeast. The house has two bedrooms and a …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Smoking allowed - ask
  • Suitable for children - over five
  • Suitable for the elderly - ask

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$286

4 BR / 2 BA / Sleeps 8

1 / 8

$286

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1167 - CHARMING HOME W/VIEWS OF VINEYARD SOUND & ELIZABETH ISLANDS

4 BR / 2 BA / Sleeps 8 | Quick view

Details

C-H-A-R-M-I-N-G is the only word to describe this privately set little contemporary with a big heart, tucked right into the woods in Spring Point. Lovely view of the Sound over the tree tops from the full length deck...dine inside comfort of screened-in porch. Convenient kitchen opens into living and dining area. …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Porch
  • Smoking allowed - ask
  • Suitable for children - over five
  • Suitable for the elderly - ask

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$858

6 BR / 4 BA / Sleeps 12

1 / 22

$858

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1148 - Chilmark Vacation Home with Lovely Views

6 BR / 4 BA / Sleeps 12 | Quick view

Details

Historic 18th century New England home in a private landscaped setting on two and 1/2 acres with a waterview over Vineyard Sound and the Elizabeth Islands; a detached two-car garage, bunkhouse and tennis court located on Menemsha Inn Road in the Town of Chilmark. The dwelling is a charming and spacious Cape design, …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Washing Machine
  • Smoking allowed - ask
  • Suitable for children - over five
  • Suitable for the elderly - 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

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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
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