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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, 114 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, 48 reviews
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, 66 reviews
Top guest favourite
Home in Chilmark
Renovated Barn in Chilmark 3BR
3 bedrooms, 4 beds, 2 bathrooms
22–29 Aug
4.99 out of 5 average rating, 106 reviews
Top guest favourite
Home in Chilmark
The Blueberry House on Martha’s Vineyard
2 bedrooms, 2 beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 27 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
Home in Chilmark
Chilmark Cape in private wooded setting
4 bedrooms, 5 beds, 2 bathrooms
31 Aug – 5 Sept
4.86 out of 5 average rating, 69 reviews
Home in Chilmark
Mid-Century Gem with Private Pool & Ocean Views
4 bedrooms, 2 bathrooms
27 Aug – 1 Sept
4.56 out of 5 average rating, 25 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, 99 reviews
Guest favourite
Home in Chilmark
Charming North Road Retreat
4 bedrooms, 5 beds, 4 bathrooms
31 Aug – 7 Sept
5.0 out of 5 average rating, 5 reviews
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, 93 reviews
Guest favourite
Home in West Tisbury
Vineyard Meadow Writer's Cottage with Hot Tub
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.97 out of 5 average rating, 61 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, 239 reviews
Top guest favourite
Home in Chilmark
South House, Up-Island Living
3 bedrooms, 3 beds, 2 bathrooms
2–7 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in West Tisbury
Beloved 5-bedroom with fenced in yard and hot tub
5 bedrooms, 8 beds, 3 bathrooms
23–28 Aug
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in West Tisbury
Sanctuary House: An ocean-view farmhouse retreat
4 bedrooms, 5 beds, 2 bathrooms
5–10 Sept
4.93 out of 5 average rating, 28 reviews
Superhost
Cottage in Chilmark
Charming 1 BR Ocean View Cottage, Path to Beach
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.94 out of 5 average rating, 17 reviews
Home in Chilmark
Tranquil Chilmark retreat
3 bedrooms, 4 beds, 2 bathrooms
23–30 Aug
5.0 out of 5 average rating, 4 reviews
Home in Chilmark
Secluded 3 bedroom home with private beach access
4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 16 reviews