Chilmark Rentals


Our Chilmark rentals are located in the small, rural community toward the western end of Martha's Vineyard. Most of it's 34 square miles are devoted to residential and agricultural use – you can get fresh flowers from a self-serve stand at Beetlebung Corner, Island-raised lamb and wool items knit from their own sheep at the Allen Farm, 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 will not 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 festivals 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 sunsets in Menemsha, a traditional fishing village. Menemsha Beach tends to have a full attendance each evening with a 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 in the mornings from 9-12 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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  • Property Highlights
    Area: Chilmark
    Turnover Day: Sunday
    Pets Allowed: No
    • 4Bedrooms:
    • 2.0Baths:
    • 8Sleeps:
  • Description:
    BR1 King first floor, BR2 (2)Twin beds first floor, shared hall bathroom of tub and shower, BR3 (2)Twins beds second flo...Read More
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  • Property Highlights
    Area: Chilmark
    Turnover Day: Sunday
    Pets Allowed: Yes, with approval
    • 5Bedrooms:
    • 4.0Baths:
    • 10Sleeps:
  • Description:
    BR#1: Queen, w/ bath, BR#2 Twin Trundle/den, BR#3 (2) Twins and (1) Full, BR#4 Queen, BR#5 Queen, BR#4 and BR#5 Shared B...Read More
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  • Property Highlights
    Area: Chilmark
    Turnover Day: N/A
    Pets Allowed: No
    • 4Bedrooms:
    • 3.5Baths:
    • 8Sleeps:
  • Description:
    BR1 King with private bathroom of tub and shower and direct access to enclosed outdoor shower, main level, BR2 Queen, th...Read More
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  • Property Highlights
    Area: Chilmark
    Turnover Day: Sunday
    Pets Allowed: No
    • 4Bedrooms:
    • 2.0Baths:
    • 8Sleeps:
  • Description:
    BR1 Queen First Floor, BR2 Queen Second Floor, Hall bathroom of tub and shower, BR3 (2) Twin beds Second Floor, BR4 Dou...Read More
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  • Property Highlights
    Area: Chilmark
    Turnover Day: Saturday
    Pets Allowed: Yes, with approval
    • 1Bedrooms:
    • 1.0Baths:
    • 2Sleeps:
  • Description:
    Studio with a couch that pulls out....Read More
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  • Property Highlights
    Area: Chilmark
    Turnover Day: Saturday
    Pets Allowed: No
    • 3Bedrooms:
    • 2.0Baths:
    • 6Sleeps:
  • Description:
    BR1 Double, first floor, connect and hall bath, BR2 King, second floor, hall Bath, BR3 Double and (2) Twin beds. Double...Read More
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  • Property Highlights
    Area: Chilmark
    Turnover Day: N/A
    Pets Allowed: No
    • 5Bedrooms:
    • 2.5Baths:
    • 10Sleeps:
  • Description:
    BR1 Master bedroom with King Bed, en suite bath, second floor. BR2 Queen, BR3 (2) Twin beds, BR4 (2) Twin beds, BR5 (2) ...Read More
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  • Property Highlights
    Area: Chilmark
    Turnover Day: N/A
    Pets Allowed: No
    • 2Bedrooms:
    • 2.0Baths:
    • 6Sleeps:
  • Description:
    BR1 queen and one single bed, en suite of tub shower, BR2 queen and one single bed hall bath of large shower stall....Read More
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  • Property Highlights
    Area: Chilmark
    Turnover Day: N/A
    Pets Allowed: Yes, with approval
    • 5Bedrooms:
    • 3.0Baths:
    • 10Sleeps:
  • Description:
    BR1 Queen Master with en suite bath, shower stall and jacuzzi tub, main level BEDROOM WING: BR2 Queen, main level, hall ...Read More
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  • Property Highlights
    Area: Chilmark
    Turnover Day: Sunday
    Pets Allowed: No
    • 3Bedrooms:
    • 1.5Baths:
    • 6Sleeps:
  • Description:
    Contemporary split level home: BR1 King, lower level with hall bathroom of tub and shower, upper level BR2 Queen, upper ...Read More
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