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Search results; Over 1,000 homes in Chilmark

Descriptions are based on details hosts provide
Top guest favourite
Cottage in Chilmark
Renovated 1950s cottage, walk to Menemsha
5.0 out of 5 average rating, 65 reviews, 3 bedrooms, 4 beds, 3 bathrooms
5–12 Sept
Top guest favourite
Home in Chilmark
Fun, Authentic, Waterfront Cottage/air conditioned
4.98 out of 5 average rating, 46 reviews, 2 bedrooms, 4 beds, 1 bathroom
28 Sept – 3 Oct
Top guest favourite
Home in West Tisbury
Wooded cottage with Lambert’s Cove Beach access
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
6–11 Sept
Top guest favourite
Home in Chilmark
Cool, Mid Century House -- Lucy Vincent Beach!
4.95 out of 5 average rating, 44 reviews, 4 bedrooms, 5 beds, 3 bathrooms
23–28 Jul
Home in Chilmark
1964 Eliot Noyes home with ocean views
4.56 out of 5 average rating, 25 reviews, 4 bedrooms, 2 bathrooms
30 Aug – 4 Sept
Guest favourite
Home in Chilmark
Designer cottage near Menemsha Beach
5.0 out of 5 average rating, 25 reviews, 2 bedrooms, 2 beds, 2 bathrooms
30 Aug – 4 Sept
Top guest favourite
Guest house in Chilmark
Beautifully Renovated 1800s Chilmark Barn
4.95 out of 5 average rating, 98 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
Top guest favourite
Home in Chilmark
Fire pit and deck near Lucy Vincent Beach
4.98 out of 5 average rating, 90 reviews, 2 bedrooms, 2 beds, 1 bathroom
18–23 Jul
Top guest favourite
Guest house in Chilmark
Beach pass to Lucy Vincent included
4.98 out of 5 average rating, 235 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Sept
Top guest favourite
Home in Chilmark
Renovated Barn in Chilmark 3BR
4.99 out of 5 average rating, 106 reviews, 3 bedrooms, 4 beds, 2 bathrooms
22–29 Aug
Guest favourite
Home in West Tisbury
Private West Tisbury House on Freshwater Pond
4.91 out of 5 average rating, 45 reviews, 3 bedrooms, 5 beds, 2 bathrooms
12–19 Sept
Top guest favourite
Home in West Tisbury
2 acres with a wraparound porch
4.98 out of 5 average rating, 222 reviews, 4 bedrooms, 6 beds, 3 bathrooms
28 Sept – 4 Oct
Home in Chilmark
Charming North Road Retreat
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 5 beds, 4 bathrooms
31 Aug – 7 Sept
Guest favourite
Home in Chilmark
Renovated home on 3 wooded acres
4.85 out of 5 average rating, 68 reviews, 4 bedrooms, 5 beds, 2 bathrooms
31 Aug – 5 Sept
Guest favourite
Home in Aquinnah
Ocean view, walk to Lobsterville Beach
4.84 out of 5 average rating, 25 reviews, 4 bedrooms, 7 beds, 4 bathrooms
18–24 Jul
Guest favourite
Home in West Tisbury
Includes a car and beach pass
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 6 beds, 2 bathrooms
22–27 Aug
Top guest favourite
Home in West Tisbury
Writer’s cottage with a hot tub
4.97 out of 5 average rating, 61 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
Guest favourite
Place to stay in Aquinnah
Ocean-view tower with a treehouse feel
4.83 out of 5 average rating, 239 reviews, 1 bedroom, 1 bed, WC
20–25 Sept