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Search results; Over 1,000 homes in Chilmark

Top guest favourite
Guest house in Chlmark
4-Season Guest House on Historic Chilmark Estate
1 bedroom, 1 bed, 1 private bathroom
19–24 Sept
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4.99 out of 5 average rating, 115 reviews
Top guest favourite
Home in Chilmark
Fun, Authentic, Waterfront Cottage/air conditioned
2 bedrooms, 4 beds, 1 bathroom
5–10 Oct
4.98 out of 5 average rating, 51 reviews
Top guest favourite
Cottage in Chilmark
Walk to the beach: Charming Menemsha Cottage
3 bedrooms, 4 beds, 3 bathrooms
14–19 Sept
5.0 out of 5 average rating, 68 reviews
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
Top guest favourite
Home in Chilmark
The Blueberry House on Martha’s Vineyard
2 bedrooms, 2 beds, 2 bathrooms
12–17 Sept
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Home in Chilmark
Renovated Barn in Chilmark 3BR
3 bedrooms, 4 beds, 2 bathrooms
5–10 Oct
4.99 out of 5 average rating, 110 reviews
Cottage in Chilmark
Charming Chilmark cottage with Atlantic view
2 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
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
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, 246 reviews
Top guest favourite
Guest house in Chilmark
Beautifully Renovated 1800s Chilmark Barn
2 bedrooms, 3 beds, 1 bathroom
12–17 Sept
4.95 out of 5 average rating, 103 reviews
Guest favourite
Home in Chilmark
Charming North Road Retreat
4 bedrooms, 5 beds, 4 bathrooms
13–18 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Chilmark
South House, Up-Island Living
3 bedrooms, 3 beds, 2 bathrooms
12–19 Sept
5.0 out of 5 average rating, 8 reviews
Home in West Tisbury
NEW BUILD: A Love Letter to MV
4 bedrooms, 5 beds, 3.5 bathrooms
25–30 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Chilmark
Quiet, Bright & Open MV home
4 bedrooms, 7 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 11 reviews
Home in Chilmark
Classic Chilmark Charm
Individual host
21–26 Sept
Top guest favourite
Home in Chilmark
Peaceful Retreat Near Up-Island Beaches
2 bedrooms, 2 queen beds, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 95 reviews
Guest favourite
Home in West Tisbury
1800s Farmhouse | Sanctuary Trails | Pickleball
5 bedrooms, 8 beds, 3.5 bathrooms
11–16 Sept
4.93 out of 5 average rating, 14 reviews
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
Guest favourite
Holiday home in Aquinnah
Cozy, comfy, light-filled Martha’s Vineyard home
4 bedrooms, 5 beds, 2 bathrooms
19–24 Sept
4.88 out of 5 average rating, 16 reviews