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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  • Property Highlights
    Unit Code: CHIL MCAL-02
    Pets Considered: No
    Town/Area: Chilmark
    • Bedrooms:6
    • Bath:5.5
    • Sleeps:10
  • Description:
    Point B Featured Listing - This stunning architect-designed Chilmark Compound features sweeping water views from atop a... Read More
  • Property Highlights
    Unit Code: CHIL BBAR-15
    Pets Considered: Yes
    Town/Area: Chilmark
    • Bedrooms:3
    • Bath:3.5
    • Sleeps:6
  • Description:
    NEW FOR SUMMER 2024 - This Chilmark Country Retreat With Guest Cottage is tucked away on a magical, bucolic three acres... Read More

Private Hilltop Retreat In Chilmark $6,000 - $8,000 Per Week

  • Property Highlights
    Unit Code: CHIL SKHE-04
    Pets Considered: No
    Town/Area: Chilmark
    • Bedrooms:3
    • Bath:3.0
    • Sleeps:8
  • Description:
    NEW FOR SUMMER 2024: Nestled atop a serene hill in Chilmark, discover a private multi-acre property offering the... Read More

Modern Farmhouse In Central Chilmark $6,500 - $7,000 Per Week

  • Property Highlights
    Unit Code: CHIL JDEM-07
    Pets Considered: Yes
    Town/Area: Chilmark
    • Bedrooms:4
    • Bath:2.0
    • Sleeps:8
  • Description:
    NEW FOR SUMMER 2024: This newly-built Modern Farmhouse is a serene escape in the heart of central Chilmark on a private... Read More

Meadow House On Blueberry Ridge $4,200 - $4,700 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