filters

Search results; Over 1,000 homes in Chilmark

Guest favourite
Cottage in Chilmark
Vintage Chilmark Retreat
3 bedrooms, 5 beds, 2 bathrooms
21–26 Sept
,
4.95 out of 5 average rating, 41 reviews
Home in Chilmark
Mid-Century Gem with Private Pool & Ocean Views
4 bedrooms
30 Aug – 4 Sept
4.56 out of 5 average rating, 25 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
Home in Chilmark
Charming North Road Retreat
4 bedrooms, 5 beds
31 Aug – 7 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Cottage in Chilmark
Walk to the beach: Charming Menemsha Cottage
3 bedrooms, 4 beds
5–12 Sept
5.0 out of 5 average rating, 66 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, 46 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
Top guest favourite
Home in Chilmark
Cool, Mid Century House -- Lucy Vincent Beach!
4 bedrooms, 5 beds
24–29 Aug
4.95 out of 5 average rating, 44 reviews
Guest favourite
Home in Chilmark
Whalehall
3 bedrooms, 4 beds
1–6 Sept
4.8 out of 5 average rating, 5 reviews
Top guest favourite
Home in West Tisbury
Vineyard Meadow Writer's Cottage with Hot Tub
3 bedrooms, 4 beds
15–20 Aug
4.97 out of 5 average rating, 61 reviews
Guest favourite
Home in West Tisbury
Waterfront home with key to private Quansoo Beach
4 bedrooms, 6 beds
13–20 Sept
4.92 out of 5 average rating, 13 reviews
Home in Chilmark
Secluded 3 bedroom home with private beach access
4 bedrooms, 5 beds
20–25 Sept
5.0 out of 5 average rating, 16 reviews
Cottage in Aquinnah
Aquinnah beach cottage
3 bedrooms, 5 beds
19–25 Sept
5.0 out of 5 average rating, 4 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
Guest favourite
Home in West Tisbury
Private 5BR Vineyard Retreat - Peaceful & Central
5 bedrooms, 8 beds
26 Sept – 1 Oct
4.94 out of 5 average rating, 16 reviews
Guest favourite
Home in Aquinnah
Modern Aquinnah home close to the beach- 5 beds
4 bedrooms, 5 beds
26 Sept – 1 Oct
4.95 out of 5 average rating, 20 reviews
Home in Chilmark
Tranquil Chilmark retreat
3 bedrooms, 4 beds
23–30 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in West Tisbury
Tranquil & Private Waterfront Great Pond home
3 bedrooms, 4 beds
21–28 Sept
4.97 out of 5 average rating, 29 reviews
Top guest favourite
Home in Chilmark
Peaceful Retreat Near Up-Island Beaches
2 bedrooms, 2 queen beds
20–25 Sept
4.98 out of 5 average rating, 91 reviews