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Search results; Over 1,000 homes in Chilmark

Superhost
Cottage in Chilmark
Pilot House- The Famous Menemsha Inn Cottage
1 bedroom, 2 beds, 1 private bathroom
10–15 Oct
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4.92 out of 5 average rating, 13 reviews
Top guest favourite
Home in Chilmark
Fun, Authentic, Waterfront Cottage/air conditioned
2 bedrooms, 4 beds
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
15–20 Sept
5.0 out of 5 average rating, 69 reviews
Superhost
Home in Chilmark
Chilmark Cape in private wooded setting
4 bedrooms, 5 beds
4–9 Oct
4.85 out of 5 average rating, 74 reviews
Top guest favourite
Home in Chilmark
Renovated Barn in Chilmark 3BR
3 bedrooms, 4 beds
5–10 Oct
4.99 out of 5 average rating, 110 reviews
Superhost
Home in Chilmark
Evelyn's Menemsha Camp - Best Vineyard View
3 bedrooms, 4 beds
20–25 Sept
4.85 out of 5 average rating, 20 reviews
Cottage in Chilmark
Charming Chilmark cottage with Atlantic view
2 bedrooms, 3 beds
28 Sept – 3 Oct
Top guest favourite
Home in Chilmark
The Blueberry House on Martha’s Vineyard
2 bedrooms, 2 beds
21–26 Sept
5.0 out of 5 average rating, 29 reviews
Guest favourite
Home in Chilmark
Quiet, Bright & Open MV home
4 bedrooms, 7 beds
23–28 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Chilmark
Charming North Road Retreat
4 bedrooms, 5 beds
16–21 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
15–22 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
25–30 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Guest house in Chilmark
Beautifully Renovated 1800s Chilmark Barn
2 bedrooms, 3 beds
24–29 Sept
4.95 out of 5 average rating, 103 reviews
Top guest favourite
Guest house in Chlmark
4-Season Guest House on Historic Chilmark Estate
1 bedroom, 1 queen bed
19–24 Sept
4.99 out of 5 average rating, 116 reviews
Top guest favourite
Guest house in Chilmark
Beautiful Guest House in Chilmark
1 bedroom, 1 bed
14–19 Sept
4.98 out of 5 average rating, 247 reviews
Home in Aquinnah
Magical Tree House On Secluded End of Island
3 bedrooms, 3 beds
19–24 Sept
4.83 out of 5 average rating, 24 reviews
Home in Chilmark
Classic Chilmark Charm
Individual host
21–26 Sept
Guest favourite
Home in West Tisbury
Tranquil & Private Waterfront Great Pond home
3 bedrooms, 4 beds
12–19 Jun
4.97 out of 5 average rating, 32 reviews
Guest favourite
Home in West Tisbury
1800s Farmhouse | Sanctuary Trails | Pickleball
5 bedrooms, 8 beds
22–27 Sept
4.93 out of 5 average rating, 15 reviews