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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, 90 reviews
Home in Chilmark
Mid-Century Gem with Private Pool & Ocean Views
4.56 out of 5 average rating, 25 reviews, 4 bedrooms, 2 bathrooms
30 Aug – 4 Sept
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
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
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
Cottage in Chilmark
Walk to the beach: Charming Menemsha Cottage
5.0 out of 5 average rating, 66 reviews, 3 bedrooms, 4 beds, 3 bathrooms
5–12 Sept
Guest favourite
Home in Chilmark
The Blueberry House on Martha’s Vineyard
5.0 out of 5 average rating, 26 reviews, 2 bedrooms, 2 beds, 2 bathrooms
30 Aug – 4 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
24–29 Aug
Home in Chilmark
Secluded 3 bedroom home with private beach access
5.0 out of 5 average rating, 16 reviews, 4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
Guest favourite
Home in Chilmark
Whalehall
4.8 out of 5 average rating, 5 reviews, 3 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
Top guest favourite
Guest house in Chilmark
Beautifully Renovated 1800s Chilmark Barn
4.95 out of 5 average rating, 99 reviews, 2 bedrooms, 3 beds, 1 bathroom
1–6 Sept
Guest favourite
Home in Chilmark
Path to Menemsha Beach
4.88 out of 5 average rating, 8 reviews, 1 bedroom, 1 bed, 1 bathroom
25–30 Aug
Guest favourite
Home in Chilmark
Chilmark Cape in private wooded setting
4.85 out of 5 average rating, 68 reviews, 4 bedrooms, 5 beds, 2 bathrooms
31 Aug – 5 Sept
Guest favourite
Home in Chilmark
Quiet, Bright & Open MV home
5.0 out of 5 average rating, 7 reviews, 4 bedrooms, 7 beds, 2 bathrooms
6–11 Sept
Cottage in Aquinnah
Aquinnah beach cottage
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 5 beds, 1 bathroom
19–25 Sept
Top guest favourite
Guest house in Chilmark
Beautiful Guest House in Chilmark
4.98 out of 5 average rating, 237 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Sept
Guest favourite
Home in Aquinnah
Modern Aquinnah home close to the beach- 5 beds
4.95 out of 5 average rating, 20 reviews, 4 bedrooms, 5 beds, 2 bathrooms
26 Sept – 1 Oct
Guest favourite
Home in West Tisbury
Waterfront home with key to private Quansoo Beach
4.92 out of 5 average rating, 13 reviews, 4 bedrooms, 6 beds, 2.5 bathrooms
13–20 Sept
Top guest favourite
Home in West Tisbury
Vineyard Meadow Writer's Cottage with Hot Tub
4.97 out of 5 average rating, 61 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug