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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

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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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$528

3 BR / 4 BA / Sleeps 9

3 Reviews

$528

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Celebrity Owned Hilltop Watervew with Hot Tub

3 BR / 4 BA / Sleeps 9 | Quick view
“ Excellent ” 3 Reviews

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Reviews

(3)

Sprawling Hilltop Glass House admits views and entertains peace from every angle. Large south facing stone terrrace has hot tub and large table to enjoy guests and family. Please note: The calendar may not display the 1st and last dates of booked property as this house may turn over on the same day. Those days show …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(3)

Fantastic Family Retreat !

Left on Apr 18, 2011 for a stay in September 2009

Our extended family enjoyed a wonderful reunion here. The terrace was the site of some wonderful dinners! We enjoyed the hot tub almost every evening and some mornings as well. It was a little off of the main road but well worth the time to get to.
The beaches were absolutely splendid and we were surprised the water was so warm yet.
We are still talking about it hoping to return.

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$2,215

5 BR / 4 BA / Sleeps 8

1242 - MAGICAL & TRANQUIL HOME OVERLOOKNG THE OCEAN. ADD A BEACH AND WHAT COULD BE BETTER?! - Chilmark vacation rentals
1 / 13

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Located in a tranquil setting overlooking Chilmark Pond off of South Road this is a magical summer vacation spot. Additional amenities include: coffee maker, lobster pot, food processor, cd player, wine glasses, crib, cassette, pillows, outside shower, blankets, ironing board.
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Smoking allowed - ask
  • Suitable for children - over five
  • Suitable for the elderly - ask

PreviousNext property

$2,000

5 BR / 6 BA / Sleeps 10

1522 - WATERFRONT VINEYARD CONTEMPORARY HOME LOCATED ON TISBURY GREAT POND - Chilmark vacation rentals
1 / 16

$2,000

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1522 - WATERFRONT VINEYARD CONTEMPORARY HOME LOCATED ON TISBURY GREAT POND

5 BR / 6 BA / Sleeps 10 | Quick view

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Vacation in Chilmark near the pristine shores of the Tisbury Great Pond in this brand new, 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 …
  • 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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$643

4 BR / 2 BA / Sleeps 8

1470 - Relax in the Pool and Enjoy Beautiful Views from this Vineyard Home - Chilmark vacation rentals
1 / 18

$643

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1470 - Relax in the Pool and Enjoy Beautiful Views from this Vineyard Home

4 BR / 2 BA / Sleeps 8 | Quick view

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A fascinating, lovely classic Eliot Noyes (architect) contemporary in a private setting with spectacular views off the water looking toward Lucy Vincent beach and East towards West Tisbury. There is a great room (with dining, and living room and kitchen) with decks on either side (4-10 feet off the ground with two …
  • 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

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$1,429

4 BR / 0 BA / Sleeps 9

#2061 Rental access to two keyed private association beaches - Chilmark vacation rentals
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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$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
  • Wheelchair accessible - ask

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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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$2,858

6 BR / 0 BA / Sleeps 12

1 / 14

$2,858

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#2060 Situated high up from the water with fabulous views

6 BR / Sleeps 12 | Quick view

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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

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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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$1,143

4 BR / 0 BA / Sleeps 10

1 / 26

$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
  • Deck
  • Grill
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,429

5 BR / 0 BA / Sleeps 10

1 / 21

$1,429

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#2064 This sprawling farm house is a found jewel

5 BR / Sleeps 10 | Quick view

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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

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$500

4 BR / 0 BA / Sleeps 10

1 / 14

$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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$358

5 BR / 0 BA / Sleeps 10

1 / 17

$358

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#2020 A grand summer house, where memories are made

5 BR / Sleeps 10 | Quick view

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A grand summer house on Martha's Vineyard where memories are made. This landmark, hilltop Victorian offers magnificent 270-degree views over meadows, Menemsha Pond and the North shore. Access to Hancock Beach with adjacent parking, as well as Menemsha pond within walking distance. Two spacious living rooms, front hall…
  • Ocean or water views
  • Internet Access
  • Deck
  • Grill
  • 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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$172

3 BR / 0 BA / Sleeps 6

1 / 12

$172

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#2025 Delightfuf guest house with sweeping water views

3 BR / Sleeps 6 | Quick view

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Delightful Cape GUEST HOUSE situated on the grounds of a hilltop Chilmark estate. (Estate's Main House is rented separately and may be occupied). Magnificent views over Menemsha Pond. Access to Hancock Beach with adjacent parking and Menemsha Pond within walking distance. First floor has an open kitchen, dining and …
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Deck
  • Dishwasher
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$572

4 BR / 0 BA / Sleeps 8

1 Reviews

$572

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#2021 Chilmark Waterfront w Dock

4 BR / Sleeps 8 | Quick view
“ Excellent ” 1 Reviews

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Reviews

(1)

Chilmark waterfront rental home located on Quitsa Pond with views across Quitsa and Menemsha ponds out to the Elizabeth Islands. This martha's vineyard rental property offers dock, mooring along with access to small beach area just down the path on Clam Point Cove. Named appropriately, it is an ideal location for …
  • 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

Details

Reviews

(1)

Chilling in Chilmark

Left on Sep 03, 2014 for a stay in August 2014

Our family thoroughly enjoyed our week at the Mayhew home in Chilmark. We rented kayaks for some boating right off the private pier, picked clams, swam off the docked and cooked out on the deck! Can't wait to go back next year.

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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

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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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$929

5 BR / 0 BA / Sleeps 10

1 / 15

$929

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

5 BR / Sleeps 10 | Quick view

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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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$286

4 BR / 5 BA / Sleeps 8

1 Reviews

$286

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653 - ATLANTIC OCEAN BREEZES,GLORIOUS VIEWS!

4 BR / 5 BA / Sleeps 8 | Quick view
“ Excellent ” 1 Reviews

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Reviews

(1)

A boutique hotel experience in an unrivaled setting at the end of a one mile single lane road. Enjoy the sunrise from the ocean, sunset over the adjoining 13 acre Sheriff's Meadow Foundation conservation preserve. This home has a wonderful view toward Squibnocket Beach, a mile away, and the Squibnocket Peninsula, with…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - over five
  • Suitable for the elderly - ask

Details

Reviews

(1)

Fabulous stay

Left on Jun 16, 2014 for a stay in March 2014

We stayed at this gorgeous home with a large family group in March. Fortunately for us, the weather was ideal. We had a lovely stay - everything at the house was wonderful and everyone loved being at this home and on the Vineyard for a winter vacation. The house is spacious, comfortable and very beautiful. The property is private.

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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

4 BR / 3 BA / Sleeps 8 | Quick view

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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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$1,072

6 BR / 5 BA / Sleeps 10

1 / 21

$1,072

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229 - ARCHITECTURAL AWARD WINNING HOME WITH PANORAMIC VIEWS OF THE VINEYARD SOUND

6 BR / 5 BA / Sleeps 10 | Quick view

Details

Spacious, 10 room, architectual award-winning design home perched atop a hill w/panoramic view of Vineyard Sound and the Elizabeth Islands. The large deck has marvelous water views and the sunsets are spectacular! Its charming interior includes a Living Room with vaulted ceilings,fireplace and bar;large, fully …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Washing Machine
  • Smoking allowed - ask
  • Suitable for children - over five
  • Suitable for the elderly - ask

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$643

4 BR / 3 BA / Sleeps 8

1 / 7

$643

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1505 - ENJOY OCEAN VIEWS FROM THIS CHILMARK HOME

4 BR / 3 BA / Sleeps 8 | Quick view

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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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$686

3 BR / 3 BA / Sleeps 6

1 / 16

$686

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746 - THE ESSENCE OF THE ISLAND WIITH ASSOCIATION BEACH

3 BR / 3 BA / Sleeps 6 | Quick view

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Beautifully restored, maintained, and furnished, this 1740 Island farmhouse is situated on 80 private acres of glorious Chilmark hills overlooking Menemsha Pond and includes a small private association beach on Menemsha Pond to wend your way down to. A little bit of heaven on earth! Additional amenities include: …
  • 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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$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
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Deck
  • 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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$1,572

5 BR / 4 BA / Sleeps 10

1 / 16

Details

Contemporary, private, exquisite home set right on Tisbury Great Pond. Drive to Quansoo or kayak right from the house. Large, gorgeous gourmet kitchen, spacious living room with stylish fire place, large screened porch, water views through the trees all contribute to the heightened appeal of this property. The guest …
  • Waterfront
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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