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: Saturday
    Pets Allowed: No
    • 3Bedrooms:
    • 2.0Baths:
    • 6Sleeps:
  • Description:
    BR1 King en suite, 1st floorBR2 Twin trundle bed, 1st floorBR3 Double, 1st floorHall bathroom, 1st floor...Read More
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  • Property Highlights
    Area: Chilmark
    Turnover Day: Sunday
    Pets Allowed: No
    • 4Bedrooms:
    • 2.0Baths:
    • 8Sleeps:
  • Description:
    BR1 King, 1st floorBR2 (2)Twin beds, 1st floorHall bath tub/shower, 1st floorBR3 (2)Twins beds, 2nd floorBR4 (2)Twin bed...Read More
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  • Property Highlights
    Area: Chilmark
    Turnover Day: Sunday
    Pets Allowed: No
    • 3Bedrooms:
    • 1.5Baths:
    • 6Sleeps:
  • Description:
    BR1 King, lower levelHall bath tub/shower, lower levelBR2 Queen, upper levelBR3 (2)Twin beds, upper levelHalf bath, uppe...Read More
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  • Property Highlights
    Area: Chilmark
    Turnover Day: N/A
    Pets Allowed: No
    • 8Bedrooms:
    • 4.0Baths:
    • 18Sleeps:
  • Description:
    Main house:BR1 King en suite separate tub and shower, 2nd floorBR2 Queen en suite tub/shower, 1st floorBR3 Queen and Twi...Read More
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  • Property Highlights
    Area: Chilmark
    Turnover Day: Saturday
    Pets Allowed: No
    • 4Bedrooms:
    • 3.0Baths:
    • 8Sleeps:
  • Description:
    BR1 King en suite with shower, 1st floor (handicap accessible)BR2 Queen, 1st floorHall bath shower stall, 1st floorBR3 (...Read More
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  • Property Highlights
    Area: Chilmark
    Turnover Day: Saturday
    Pets Allowed: Yes, with approval
    • 6Bedrooms:
    • 5.5Baths:
    • 13Sleeps:
  • Description:
    BR1 King en suite with shower, 1st floor (private deck & outdoor shower)BR2 Queen en suite with tub/shower, 1st floorBR3...Read More
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  • Property Highlights
    Area: Chilmark
    Turnover Day: Sunday
    Pets Allowed: No
    • 4Bedrooms:
    • 2.0Baths:
    • 8Sleeps:
  • Description:
    BR1 Queen, 1st floorHall bath tub/shower, 1st floorBR2 Queen, 2nd floorBR3 (2)Twin beds, 2nd floorBR4 Double, 2nd floorH...Read More
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  • Property Highlights
    Area: Chilmark
    Turnover Day: Saturday
    Pets Allowed: Yes, with approval
    • 3Bedrooms:
    • 1.5Baths:
    • 6Sleeps:
  • Description:
    BR1 Double futon bed in den, 1st floorBR2 King with half bath, 2nd floorBR3 (2)Twin beds, 2nd floorHall bath shower, 1st...Read More
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  • Property Highlights
    Area: Chilmark
    Turnover Day: Monday
    Pets Allowed: No
    • 4Bedrooms:
    • 3.5Baths:
    • 8Sleeps:
  • Description:
    BR1 King en suite with tub and shower, 2nd floorBR2 Double, 2nd floorBR3 Double, 2nd floorHall bath tub/shower, 2nd floo...Read More
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  • Property Highlights
    Area: Chilmark
    Turnover Day: Saturday
    Pets Allowed: No
    • 6Bedrooms:
    • 4.5Baths:
    • 15Sleeps:
  • Description:
    Main house:BR1 Queen en suite with shower stall and sun room, 1st floorBR2 Queen en suite, 1st floor(newly added in 2019...Read More
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