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Search results; Over 1,000 homes in Chilmark

Top guest favourite
Home in Chilmark
Peaceful Retreat Near Up-Island Beaches
2 bedrooms, 2 beds, 1 shared bathroom
20–25 Sept
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4.98 out of 5 average rating, 93 reviews
Top guest favourite
Home in Chilmark
Fun, Authentic, Waterfront Cottage/air conditioned
2 bedrooms, 4 beds
28 Sept – 3 Oct
4.98 out of 5 average rating, 48 reviews
Top guest favourite
Guest house in Chilmark
Beautifully Renovated 1800s Chilmark Barn
2 bedrooms, 3 beds
1–6 Sept
4.95 out of 5 average rating, 99 reviews
Top guest favourite
Home in Chilmark
The Blueberry House on Martha’s Vineyard
2 bedrooms, 2 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 27 reviews
Guest favourite
Home in Chilmark
Chilmark Cape in private wooded setting
4 bedrooms, 5 beds
31 Aug – 5 Sept
4.86 out of 5 average rating, 69 reviews
Top guest favourite
Guest house in Chilmark
Beautiful Guest House in Chilmark
1 bedroom, 1 bed
13–18 Sept
4.98 out of 5 average rating, 239 reviews
Superhost
Home in Chilmark
Evelyn's Menemsha Camp - Best Vineyard View
3 bedrooms, 4 beds
20–25 Sept
4.85 out of 5 average rating, 20 reviews
Top guest favourite
Cottage in Chilmark
Walk to the beach: Charming Menemsha Cottage
3 bedrooms, 4 beds
14–21 Sept
5.0 out of 5 average rating, 66 reviews
Top guest favourite
Home in Chilmark
Renovated Barn in Chilmark 3BR
3 bedrooms, 4 beds
22–29 Aug
4.99 out of 5 average rating, 106 reviews
Superhost
Hotel in Chilmark
Sage Room @The Beach Plum Inn
1 bedroom, 1 bed
13–18 Sept
4.75 out of 5 average rating, 4 reviews
Guest favourite
Place to stay in Aquinnah
Water View "Tower" Room on Martha's Vineyard
1 bedroom, 1 bed
20–25 Sept
4.83 out of 5 average rating, 241 reviews
Top guest favourite
Guest suite in West Tisbury
The Loft Guest Suite. Private. Newly Renovated.
1 queen bed
14–19 Sept
4.94 out of 5 average rating, 181 reviews
Superhost
Cottage in Chilmark
Charming 1 BR Ocean View Cottage, Path to Beach
1 bedroom, 2 beds
30 Aug – 4 Sept
4.94 out of 5 average rating, 17 reviews
Top guest favourite
Guest house in West Tisbury
Vineyard Meadow Artist Studio
3 beds
20–25 Sept
4.98 out of 5 average rating, 121 reviews
Guest favourite
Home in Chilmark
Charming North Road Retreat
4 bedrooms, 5 beds
31 Aug – 7 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Guest house in West Tisbury
Country cottage walk to Alley's General Store
1 bed
6–11 Sept
4.99 out of 5 average rating, 110 reviews
Top guest favourite
Guest house in Chlmark
4-Season Guest House on Historic Chilmark Estate
1 bedroom, 1 queen bed
19–24 Sept
4.99 out of 5 average rating, 114 reviews
Guest favourite
Home in West Tisbury
Vineyard Meadow Writer's Cottage with Hot Tub
3 bedrooms, 4 beds
7–12 Sept
4.97 out of 5 average rating, 61 reviews
Home in Chilmark
Mid-Century Gem with Private Pool & Ocean Views
4 bedrooms
27 Aug – 1 Sept
4.56 out of 5 average rating, 25 reviews