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Search results; Over 1,000 homes in Chilmark

Top guest favourite
Cottage in Chilmark
Walk to the beach: Charming Menemsha Cottage
3 bedrooms, 4 beds, 3 private bathrooms
14–21 Sept
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5.0 out of 5 average rating, 67 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
31 Aug – 5 Sept
4.85 out of 5 average rating, 71 reviews
Top guest favourite
Guest house in Chilmark
Beautiful Guest House in Chilmark
1 bedroom, 1 bed, 1 bathroom
2–7 Sept
4.98 out of 5 average rating, 242 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
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
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
Superhost
Cottage in Chilmark
Menemsha Cottage
1 bedroom, 1 king bed, 1 bathroom
18–23 Sept
5.0 out of 5 average rating, 10 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, 109 reviews
Top guest favourite
Guest suite in West Tisbury
The Loft Guest Suite. Private. Newly Renovated.
1 queen bed, 1 bathroom
27 Sept – 2 Oct
4.95 out of 5 average rating, 184 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
Guest favourite
Room in Chilmark
Astilbe Room @ Beach Plum Inn
1 bed, 1 bathroom
30 Aug – 4 Sept
4.86 out of 5 average rating, 7 reviews
Superhost
Room in Chilmark
Cosmos @ The Beach Plum Inn
1 king bed, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Guest house in West Tisbury
Vineyard Meadow Artist Studio
3 beds, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 122 reviews
Top guest favourite
Guest house in West Tisbury
Country cottage walk to Alley's General Store
1 bed, 1 bathroom
6–11 Sept
4.98 out of 5 average rating, 113 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
Top guest favourite
Room in West Tisbury
warm and spacious B and B in our Martha's Vin home
1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 48 reviews