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Search results; Over 1,000 homes in Chilmark

Top guest favourite
Home in Chilmark
Peaceful Retreat Near Up-Island Beaches
2 bedrooms, 2 beds, 1 shared bathroom
18–23 Jul
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4.98 out of 5 average rating, 90 reviews
Top guest favourite
Home in Chilmark
Fun, Authentic, Waterfront Cottage/air conditioned
4.98 out of 5 average rating, 46 reviews, 2 bedrooms, 4 beds, 1 bathroom
28 Sept – 3 Oct
Top guest favourite
Cottage in Chilmark
Walk to the beach: Charming Menemsha Cottage
5.0 out of 5 average rating, 65 reviews, 3 bedrooms, 4 beds, 3 bathrooms
5–12 Sept
Home in Chilmark
Mid-Century Gem with Private Pool & Ocean Views
4.56 out of 5 average rating, 25 reviews, 4 bedrooms, 2 bathrooms
30 Aug – 4 Sept
Top guest favourite
Home in Chilmark
Cool, Mid Century House -- Lucy Vincent Beach!
4.95 out of 5 average rating, 44 reviews, 4 bedrooms, 5 beds, 3 bathrooms
23–28 Jul
Guest favourite
Home in Chilmark
The Blueberry House on Martha’s Vineyard
5.0 out of 5 average rating, 25 reviews, 2 bedrooms, 2 beds, 2 bathrooms
30 Aug – 4 Sept
Top guest favourite
Guest house in Chilmark
Beautifully Renovated 1800s Chilmark Barn
4.95 out of 5 average rating, 98 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
Home in Chilmark
Charming North Road Retreat
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 5 beds, 4 bathrooms
31 Aug – 7 Sept
Top guest favourite
Home in Chilmark
Renovated Barn in Chilmark 3BR
4.99 out of 5 average rating, 106 reviews, 3 bedrooms, 4 beds, 2 bathrooms
22–29 Aug
Guest favourite
Home in Chilmark
Path to Menemsha Beach
4.88 out of 5 average rating, 8 reviews, 1 bedroom, 1 bed, 1 bathroom
25–30 Jul
Top guest favourite
Home in West Tisbury
Cozy 3BR Cottage with Lambert's Cove Beach access
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
6–11 Sept
Top guest favourite
Home in West Tisbury
Up-Island Escape, Long Point Beach
4.98 out of 5 average rating, 222 reviews, 4 bedrooms, 6 beds, 3 bathrooms
28 Sept – 4 Oct
Guest favourite
Home in West Tisbury
3BR Home, Fenced Yard, Free use of car, Pets ok!
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 6 beds, 2 bathrooms
22–27 Aug
Guest favourite
Place to stay in West Tisbury
Historical farmhouse on 87 acres
4.8 out of 5 average rating, 5 reviews, 1 bedroom, 1 bed, 1 bathroom
20–25 Jul
Guest favourite
Home in Aquinnah
MARTHA'S VINEYARD AQUINNAH OCEAN VIEW CLAY PIT RD
4.84 out of 5 average rating, 25 reviews, 4 bedrooms, 7 beds, 4 bathrooms
18–24 Jul
Guest favourite
Home in Chilmark
Chilmark Cape in private wooded setting
4.85 out of 5 average rating, 68 reviews, 4 bedrooms, 5 beds, 2 bathrooms
31 Aug – 5 Sept
Top guest favourite
Home in West Tisbury
Vineyard Meadow Writer's Cottage with Hot Tub
4.97 out of 5 average rating, 61 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
Home in West Tisbury
West Tisbury Private Oasis
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
Guest favourite
Home in Chilmark
Quiet, Bright & Open MV home
5.0 out of 5 average rating, 7 reviews, 4 bedrooms, 7 beds, 2 bathrooms
6–11 Sept