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Search results; Over 1,000 homes in Chilmark

Descriptions are based on details hosts provide
Guest favourite
Home in Chilmark
Cozy Waterfront Cottage, Newly Remodeled!
4 bedrooms, 4 beds, 2 private bathrooms
30 Aug – 6 Sept
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4.86 out of 5 average rating, 69 reviews
Top guest favourite
Cottage in Chilmark
Renovated 1950s cottage, walk to Menemsha
3 bedrooms, 4 beds, 3 bathrooms
5–12 Sept
5.0 out of 5 average rating, 65 reviews
Top guest favourite
Home in Chilmark
Waterfront cottage with stunning sunset views
2 bedrooms, 4 beds, 1 bathroom
28 Sept – 3 Oct
4.98 out of 5 average rating, 46 reviews
Top guest favourite
Home in Chilmark
Mid-century home with a heated pool
4 bedrooms, 5 beds, 3 bathrooms
23–28 Jul
4.95 out of 5 average rating, 44 reviews
Home in Chilmark
Mid-Century Gem with Private Pool & Ocean Views
4 bedrooms, 2 bathrooms
30 Aug – 4 Sept
4.56 out of 5 average rating, 25 reviews
Top guest favourite
Guest house in Chilmark
Renovated 1800s barn with original beams
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
4.95 out of 5 average rating, 98 reviews
Guest favourite
Home in Chilmark
Designer cottage near Menemsha Beach
2 bedrooms, 2 beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Home in Chilmark
Fire pit and deck near Lucy Vincent Beach
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Jul
4.98 out of 5 average rating, 90 reviews
Top guest favourite
Home in West Tisbury
Wooded cottage with Lambert’s Cove Beach access
3 bedrooms, 5 beds, 2.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 7 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, 106 reviews
Home in Chilmark
Charming North Road Retreat
4 bedrooms, 5 beds, 4 bathrooms
7–14 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in West Tisbury
3BR Home, Fenced Yard, Free use of car, Pets ok!
3 bedrooms, 6 beds, 2 bathrooms
22–27 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
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, 68 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, 235 reviews
Top guest favourite
Home in West Tisbury
Vineyard Meadow Writer's Cottage with Hot Tub
3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
4.97 out of 5 average rating, 61 reviews
Guest favourite
Home in Aquinnah
Modern Aquinnah home close to the beach- 5 beds
4 bedrooms, 5 beds, 2 bathrooms
26 Sept – 1 Oct
4.95 out of 5 average rating, 20 reviews
Guest favourite
Home in West Tisbury
Vineyard retreat with beach access included
5 bedrooms, 8 beds, 2 bathrooms
26 Sept – 1 Oct
4.94 out of 5 average rating, 16 reviews
Home in Chilmark
Great screen porch and fun house
4 bedrooms, 6 beds, 2 bathrooms
20–26 Sept
Home in Chilmark
Tranquil Chilmark retreat
3 bedrooms, 4 beds, 2 bathrooms
19–26 Jul
5.0 out of 5 average rating, 4 reviews