Chillmark Vacation Rentals

With a population density of fewer than 50 people per square mile – the lowest on Martha’s Vineyard – Chilmark is truly a place to get away from it all. It’s been the favored vacation spot of President Obama and his family, and it’s easy to see why. It offers sprawling farmland, elegant residences, and wooded and grassland properties bordered by miles of centuries-old stone walls. Search for the perfect rental below. You can also view all of our Martha's Vineyard Vacation Rentals.  Or search for rentals in EdgartownEdgartown VillageKatamaOak Bluffs, Vineyard Haven Tisbury, or West Tisbury.

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Sunset Views At Spring Point Beach House $3,500 - $7,500 Per Week

  • Property Highlights
    Unit Code: CHIL JSHE-63
    Pets Considered: No
    Town/Area: Chilmark
    • Bedrooms:2
    • Bath:2.0
    • Sleeps:4
  • Description:
    Point B Featured Listing - This newly renovated Chilmark Beach House sits atop the bluff in the prestigious Spring Point... Read More

Meadow House On Blueberry Ridge $4,025 - $4,100 Per Week

  • Property Highlights
    Unit Code: CHIL VBAR-39GH
    Pets Considered: No
    Town/Area: Chilmark
    • Bedrooms:2
    • Bath:1.0
    • Sleeps:4
  • Description:
    Quietly tucked away in a pastoral setting on Blueberry Ridge, Meadow House features a modern interpretation of a sleek... Read More