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Search results; Over 1,000 homes in Chilmark

Top guest favourite
Home in Chilmark
The Blueberry House on Martha’s Vineyard
2 bedrooms, 2 beds, 2 private bathrooms
1–6 Sept
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5.0 out of 5 average rating, 28 reviews
Top guest favourite
Cottage in Chilmark
Walk to the beach: Charming Menemsha Cottage
3 bedrooms, 4 beds, 3 bathrooms
14–21 Sept
5.0 out of 5 average rating, 67 reviews
Superhost
Home in Chilmark
Evelyn's Menemsha Camp - Best Vineyard View
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.85 out of 5 average rating, 20 reviews
Top guest favourite
Home in Chilmark
Fun, Authentic, Waterfront Cottage/air conditioned
2 bedrooms, 4 beds, 1 bathroom
28 Sept – 3 Oct
4.98 out of 5 average rating, 49 reviews
Superhost
Home in Chilmark
Chilmark Cape in private wooded setting
4 bedrooms, 5 beds, 2 bathrooms
12–17 Sept
4.85 out of 5 average rating, 73 reviews
Guest favourite
Home in Chilmark
Charming North Road Retreat
4 bedrooms, 5 beds, 4 bathrooms
1–8 Sept
5.0 out of 5 average rating, 6 reviews
Cottage in Chilmark
Charming Chilmark cottage with Atlantic view
2 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
Guest favourite
Home in Chilmark
Tucked away on Tea Lane, Chilmark
4 bedrooms, 8 beds, 2.5 bathrooms
1–8 Sept
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Home in Chilmark
Renovated Barn in Chilmark 3BR
3 bedrooms, 4 beds, 2 bathrooms
30 Sept – 5 Oct
4.99 out of 5 average rating, 109 reviews
Home in Chilmark
Mid-Century Gem with Private Pool & Ocean Views
4 bedrooms, 2 bathrooms
29 Sept – 4 Oct
4.59 out of 5 average rating, 27 reviews
Top guest favourite
Guest house in Chilmark
Beautiful Guest House in Chilmark
1 bedroom, 1 bed, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 243 reviews
Guest favourite
Home in West Tisbury
Tranquil & Private Waterfront Great Pond home
3 bedrooms, 4 beds, 3 bathrooms
21–28 Sept
4.97 out of 5 average rating, 30 reviews
Guest favourite
Home in West Tisbury
Secluded and Serene Getaway
5 bedrooms, 12 beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Guest house in Chilmark
Beautifully Renovated 1800s Chilmark Barn
2 bedrooms, 3 beds, 1 bathroom
1–6 Sept
4.95 out of 5 average rating, 101 reviews
Top guest favourite
Home in Chilmark
South House, Up-Island Living
3 bedrooms, 3 beds, 2 bathrooms
2–7 Sept
5.0 out of 5 average rating, 7 reviews
Home in West Tisbury
6BR Tisbury Great Pond/ Private Chilmark Beach
6 bedrooms, 8 beds, 3 bathrooms
1–8 Sept
Home in Chilmark
Great screen porch and fun house
4 bedrooms, 6 beds, 2 bathrooms
20–26 Sept
Home in Chilmark
Classic Chilmark Charm
7 bedrooms, 8 beds, 3.5 bathrooms
4–9 Sept
Top guest favourite
Home in West Tisbury
Charming West Tisbury Home
5 bedrooms, 4 beds, 4.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 17 reviews