filters

Search results; Over 1,000 homes in Chilmark

Photo 1 of 6
Superhost
Home in Chilmark
The Blueberry House on Martha’s Vineyard
2 bedrooms, 2 beds, 2 private bathrooms
1–6 Sept
,
5.0 out of 5 average rating, 28 reviews
Photo 1 of 6
Top guest favourite
Cottage in Chilmark
Walk to the beach: Charming Menemsha Cottage
3 bedrooms, 4 beds, 3 bathrooms
14–21 Sept
5.0 out of 5 average rating, 67 reviews
Photo 1 of 6
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
Photo 1 of 6
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
Photo 1 of 6
Superhost
Home in Chilmark
Chilmark Cape in private wooded setting
4 bedrooms, 5 beds, 2 bathrooms
12–17 Sept
4.85 out of 5 average rating, 73 reviews
Photo 1 of 6
Guest favourite
Home in Chilmark
Charming North Road Retreat
4 bedrooms, 5 beds, 4 bathrooms
1–6 Sept
5.0 out of 5 average rating, 6 reviews
Photo 1 of 6
Home in West Tisbury
NEW Luxury Home: Aug/Sept Special
4 bedrooms, 5 beds, 3.5 bathrooms
8–13 Sept
Photo 1 of 6
Cottage in Chilmark
Charming Chilmark cottage with Atlantic view
2 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
Photo 1 of 6
Top guest favourite
Home in Chilmark
Renovated Barn in Chilmark 3BR
3 bedrooms, 4 beds, 2 bathrooms
30 Sept – 5 Oct
4.99 out of 5 average rating, 109 reviews
Photo 1 of 6
Top guest favourite
Guest house in Chilmark
Beautiful Guest House in Chilmark
1 bedroom, 1 bed, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 244 reviews
Photo 1 of 6
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
Photo 1 of 6
Guest favourite
Home in West Tisbury
Tranquil & Private Waterfront Great Pond home
3 bedrooms, 4 beds, 3 bathrooms
21–28 Sept
4.97 out of 5 average rating, 30 reviews
Photo 1 of 6
Guest favourite
Cottage in Chilmark
CHILMARK HILLTOP OCEAN VIEW
5 bedrooms, 5 beds, 2 bathrooms
6–11 Sept
4.86 out of 5 average rating, 21 reviews
Photo 1 of 6
Home in Aquinnah
Magical Tree House On Secluded End of Island
3 bedrooms, 3 beds, 1.5 bathrooms
19–24 Sept
4.83 out of 5 average rating, 24 reviews
Photo 1 of 6
Superhost
Room in Chilmark
Oceanview Inn Room (Single King or Double Queens)
1 king bed, 1 bathroom
6–11 Sept
New place to stay
Photo 1 of 6
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
Photo 1 of 6
Guest favourite
Home in West Tisbury
Spacious, Private Cape in W. Tisbury
4 bedrooms, 6 beds, 3 bathrooms
14–21 Sept
5.0 out of 5 average rating, 7 reviews
Photo 1 of 6
Guest favourite
Home in West Tisbury
Secluded and Serene Getaway
5 bedrooms, 12 beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 9 reviews
Photo 1 of 6
Home in Chilmark
Classic Chilmark Charm
7 bedrooms, 8 beds, 3.5 bathrooms
4–9 Sept