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Search results; Over 1,000 homes in Chilmark

Top guest favourite
Cottage in Chilmark
Walk to the beach: Charming Menemsha Cottage
3 bedrooms, 4 beds, 3 private bathrooms
14–21 Sept
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5.0 out of 5 average rating, 67 reviews
Top guest favourite
Guest house in Chilmark
Beautiful Guest House in Chilmark
1 bedroom, 1 bed, 1 bathroom
2–7 Sept
4.98 out of 5 average rating, 243 reviews
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
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
Top guest favourite
Home in Chilmark
The Blueberry House on Martha’s Vineyard
2 bedrooms, 2 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 28 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, 71 reviews
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
Guest favourite
Room in Chilmark
Astilbe Room @ Beach Plum Inn
1 bed, 1 bathroom
1–6 Sept
4.86 out of 5 average rating, 7 reviews
Guest favourite
Home in Chilmark
Bayberry Cottage- Menemsha Inn & Lucy
1 bedroom, 2 beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Chilmark
Charming North Road Retreat
4 bedrooms, 5 beds, 4 bathrooms
1–8 Sept
5.0 out of 5 average rating, 6 reviews
Room in West Tisbury
Explore Martha's Vineyard up island getaway
1 queen bed, 1.5 bathrooms
1–6 Sept
4.85 out of 5 average rating, 20 reviews
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
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
Superhost
Flat in Chilmark
The Mainstay at Menemsha Inn
2 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
Top guest favourite
Room in West Tisbury
warm and spacious B and B in our Martha's Vin home
1 queen bed, 1 bathroom
4–9 Oct
4.98 out of 5 average rating, 48 reviews
Top guest favourite
Guest house in West Tisbury
Vineyard Meadow Artist Studio
3 beds, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 122 reviews
Superhost
Cottage in Chilmark
Charming 1 BR Ocean View Cottage, Path to Beach
1 bedroom, 2 beds, 1 bathroom
21–28 Sept
4.94 out of 5 average rating, 17 reviews
Guest favourite
Place to stay in Aquinnah
Water View "Tower" Room on Martha's Vineyard
1 bedroom, 1 bed, WC
20–25 Sept
4.83 out of 5 average rating, 242 reviews
Guest favourite
Home in Chilmark
Whalehall
3 bedrooms, 4 beds, 2 bathrooms
2–7 Sept
4.86 out of 5 average rating, 7 reviews