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Chilmark Rentals

Our Chilmark rentals are located in the small, rural community toward the western end of Martha's Vineyard. Most of its 34 square miles are devoted to residential and agricultural use – you can get fresh flowers at a Beetlebung Corner self-serve stand, Island-raised lamb at the Allen Farm and wool items knit from their own sheep, eggs from really free range chickens and bacon from local pigs. Enjoy the beautiful rolling land with rambling stone walls as you drive through many parts of Chilmark. Middle road is one of the most beautiful drives on the island.

One of the real perks to choosing from our Chilmark rentals is the access to the two town beaches, Lucy Vincent and Squibnocket, along the South Shore (surf side). This area of the island brings you back in time to enjoy the slow days of summer. Some things you won’t want to miss are the many hiking trails with Menemsha Hills being one of the highlights. Chilmark Chocolates is an all time favorite stop for anyone visiting and islanders alike. Chilmark is also fortunate to have the local Film Festival host weekly film festival each Wednesday evening starting with Cinema Circus for the children and followed by adult films. And, of course, you will not want to miss out on the fabulous sun sets in Menemsha, a traditional fishing village. Menemsha Beach tends to have full attendance each evening with wonderful applause for the show as the sun dips down into the horizon.

Not far from our Chilmark vacation rentals is The Chilmark Community Center, which offers a terrific children’s summer program that runs from 9-12n each week day along with a great tennis program for the whole family. You can sign up for the season or on a weekly basis. The center also offers many family and adult activities throughout the season.  Contact us if you'd like more information about one of the Chilmark rentals below.

 

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44 properties found

20005 Bed / 2.5 Bath / Sleeps 10

Chilmark

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Sitting at one of the highest points of the island, this lovely Chilmark home offers unsurpassed views across the Vineya...read more

20014 Bed / 4.5 Bath / Sleeps 10

Chilmark

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Spectacular waterviews! This Martha's Vineyard vacation rental is situated on 3+ acres overlooking the Elizabeth Islands...read more

20023 Bed / 2.5 Bath / Sleeps 10

Chilmark

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This is a lovely, classic, renovated farmhouse behind stone walls on large acreage in stunning Chilmark with trails and ...read more

20034 Bed / 4.5 Bath / Sleeps 8

Chilmark

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Hear the waves rolling over Stonewall Beach from every room in the house! Exquisite sunsets and views from every room. L...read more

20045 Bed / 3.0 Bath / Sleeps 10

Chilmark

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Sprawling 5 bedroom Chilmark home on waters edge at its best. This home with its understated elegance welcomes any trave...read more

20054 Bed / 2.0 Bath / Sleeps 10

Chilmark

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Clean, neat, easy "beachy" 4 bedroom plus bonus room Chilmark home with an in ground pool off of picturesque Middle Road...read more

20062 Bed / 1.5 Bath / Sleeps 5

Chilmark

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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...read more

20074 Bed / 2.5 Bath / Sleeps 9

Chilmark

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Quintessential Chilmark farm house on 12 acre estate. Renovated 1700's house offering antique qualities with the modern ...read more

20084 Bed / 3.0 Bath / Sleeps 8

Chilmark

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Bright and airy with "beachy" decor wraps you into this 4 bedroom Chilmark handicapped accessible master suite and bathr...read more

20094 Bed / 2.0 Bath / Sleeps 8

Chilmark

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The historic Look House is in Chilmark about a mile west of Beetlebung Corners. The house, built in the early 1900s, inc...read more