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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  • Property Highlights
    Area: Chilmark
    Turnover Day: Saturday
    Pets Allowed: No
    • 1Bedrooms:
    • 1.0Baths:
    • 4Sleeps:
  • Description:
    BR 1 - Queen, lower level. Double bed in loft....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: 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
    • 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: Sunday
    Pets Allowed: No
    • 6Bedrooms:
    • 5.5Baths:
    • 12Sleeps:
  • Description:
    BR#1 King, master w/ bath, main floor, BR#2 Queen, main floor, BR#3 Queen, main floor, BR#4 Queen, main floor, BR#5 Quee...Read More
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  • Property Highlights
    Area: Chilmark
    Turnover Day: N/A
    Pets Allowed: Yes, with approval
    • 4Bedrooms:
    • 2.5Baths:
    • 10Sleeps:
  • Description:
    Bedroom 1 - First floor, king bed, loft with queen, en suite bath. Bedroom 2 - First floor, full bed. Bedroom 3 - Second...Read More
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  • Property Highlights
    Area: Chilmark
    Turnover Day: Monday
    Pets Allowed: Yes, with approval
    • 4Bedrooms:
    • 2.5Baths:
    • 8Sleeps:
  • Description:
    BR1 Queen Master w en suite bath, tub shower combo, BR2, Queen, BR3 (2)Twin beds, BR4 Queen, shared hall bath w/ shower ...Read More
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  • Property Highlights
    Area: Chilmark
    Turnover Day: N/A
    Pets Allowed: No
    • 6Bedrooms:
    • 5.0Baths:
    • 13Sleeps:
  • Description:
    BR1 Queen master en suite with stall shower, BR2 Double and (1) Twin, hall bath with tub and shower, BR3 Double and (1)...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: N/A
    Pets Allowed: Yes, with approval
    • 6Bedrooms:
    • 6.5Baths:
    • 10Sleeps:
  • Description:
    Main House: BR1 Queen, first floor, BR2 King master with soaking tub, second floor, BR3 Queen, second floor, BR4 Queen, ...Read More
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