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 Edgartown, Edgartown Village, Katama, Oak Bluffs, Vineyard Haven Tisbury, or West Tisbury.

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6 properties returned | Your Current Search: Location - Chilmark

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Water View Compound In Chilmark With Guest House And Pool $45,000 - $50,000 Per Week

  • Property Highlights
    Unit Code: CHIL MCAL-02
    Pets Considered: No
    Town/Area: Chilmark
    • Bedrooms:6
    • Bath:5.5
    • Sleeps:10
  • Description:
    This stunning architect-designed Chilmark Compound features sweeping water views from atop a hillside knoll overlooking... Read More
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Chilmark Water View Home At Spring Point $11,900 - $15,000 Per Week

  • Property Highlights
    Unit Code: CHIL PBRE-23
    Pets Considered: No
    Town/Area: Chilmark
    • Bedrooms:4
    • Bath:4.5
    • Sleeps:8
  • Description:
    Perched at the highest point in Chilmark's prestigious Spring Point enclave, this recently updated home offers stunning... Read More
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Chilmark Country Retreat With Guest Cottage $3,100 - $8,500 Per Week

  • Property Highlights
    Unit Code: CHIL BBAR-15
    Pets Considered: Yes
    Town/Area: Chilmark
    • Bedrooms:3
    • Bath:3.5
    • Sleeps:6
  • Description:
    This Chilmark Country Retreat With Guest Cottage is tucked away on a magical, bucolic three acres between Middle Road... Read More
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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:
    Nestled atop a serene hill in Chilmark, discover a private multi-acre property offering the ultimate up-island getaway... Read More
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Modern Farmhouse In Central Chilmark $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:
    This newly-built Modern Farmhouse is a serene escape in the heart of central Chilmark on a private lane just off South... Read More
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Meadow House On Blueberry Ridge $4,700 - $4,900 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
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