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Search results; Over 1,000 homes in Chilmark

Home in Chilmark
Mid-Century Gem with Private Pool & Ocean Views
4 bedrooms, 2 private bathrooms
29 Sept – 4 Oct
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4.59 out of 5 average rating, 27 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
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
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
Chilmark Cape in private wooded setting
4 bedrooms, 5 beds, 2 bathrooms
31 Aug – 5 Sept
4.85 out of 5 average rating, 71 reviews
Guest favourite
Home in Chilmark
The Blueberry House on Martha’s Vineyard
2 bedrooms, 2 beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 28 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
Renovated Barn in Chilmark 3BR
3 bedrooms, 4 beds, 2 bathrooms
22–29 Aug
4.99 out of 5 average rating, 108 reviews
Guest favourite
Home in Chilmark
Charming North Road Retreat
4 bedrooms, 5 beds, 4 bathrooms
31 Aug – 7 Sept
5.0 out of 5 average rating, 6 reviews
Home in Chilmark
Classic Chilmark Charm
7 bedrooms, 8 beds, 3.5 bathrooms
4–9 Sept
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, 242 reviews
Guest favourite
Home in West Tisbury
Vineyard Meadow Writer's Cottage with Hot Tub
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.97 out of 5 average rating, 61 reviews
Superhost
Cottage in Chilmark
Chilmark, Martha' s Vineyard Water View Cottage
1 bedroom, 1 king bed, 1 bathroom
31 Aug – 5 Sept
4.83 out of 5 average rating, 12 reviews
Guest favourite
Home in West Tisbury
Spacious, Private Cape in W. Tisbury
4 bedrooms, 6 beds, 3 bathrooms
14–21 Sept
5.0 out of 5 average rating, 6 reviews
Superhost
Cottage in Chilmark
Menemsha Cottage
1 bedroom, 1 king bed, 1 bathroom
31 Aug – 5 Sept
5.0 out of 5 average rating, 10 reviews
Home in Aquinnah
Aquinnah Home by Lobsterville Beach w/ Ocean Views
4 bedrooms, 7 beds, 4 bathrooms
23–28 Aug
New place to stay
Guest favourite
Cottage in Chilmark
CHILMARK HILLTOP OCEAN VIEW
5 bedrooms, 5 beds, 2 bathrooms
6–11 Sept
4.86 out of 5 average rating, 21 reviews
Guest favourite
Home in West Tisbury
Sanctuary House: An ocean-view farmhouse retreat
4 bedrooms, 5 beds, 2 bathrooms
5–10 Sept
4.93 out of 5 average rating, 28 reviews
Top guest favourite
Home in Chilmark
Peaceful Retreat Near Up-Island Beaches
2 bedrooms, 2 queen beds, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 93 reviews