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Search results; Over 1,000 homes in Chilmark

Guest favourite
Home in Chilmark
Historic Brick Barn in Chilmark
2 bedrooms, 3 beds, 1 bathroom
17–22 Sept
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4.98 out of 5 average rating, 56 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, 46 reviews
Top guest favourite
Cottage in Chilmark
Walk to the beach: Charming Menemsha Cottage
3 bedrooms, 4 beds, 3 bathrooms
5–12 Sept
5.0 out of 5 average rating, 65 reviews
Top guest favourite
Home in Chilmark
Peaceful Retreat Near Up-Island Beaches
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Jul
4.98 out of 5 average rating, 90 reviews
Top guest favourite
Home in Chilmark
Cool, Mid Century House -- Lucy Vincent Beach!
4 bedrooms, 5 beds, 3 bathrooms
23–28 Jul
4.95 out of 5 average rating, 44 reviews
Top guest favourite
Guest house in Chilmark
Beautifully Renovated 1800s Chilmark Barn
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
4.95 out of 5 average rating, 98 reviews
Home in Chilmark
Mid-Century Gem with Private Pool & Ocean Views
4 bedrooms, 2 bathrooms
30 Aug – 4 Sept
4.56 out of 5 average rating, 25 reviews
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, 25 reviews
Home in Chilmark
Charming North Road Retreat
4 bedrooms, 5 beds, 4 bathrooms
31 Aug – 7 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Chilmark
Path to Menemsha Beach
1 bedroom, 1 bed, 1 bathroom
25–30 Jul
4.88 out of 5 average rating, 8 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
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
Guest favourite
Home in Chilmark
Chilmark Cape in private wooded setting
4 bedrooms, 5 beds, 2 bathrooms
31 Aug – 5 Sept
4.85 out of 5 average rating, 68 reviews
Top guest favourite
Home in West Tisbury
Cozy 3BR Cottage with Lambert's Cove Beach access
3 bedrooms, 5 beds, 2.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in West Tisbury
Up-Island Escape, Long Point Beach
4 bedrooms, 6 beds, 3 bathrooms
28 Sept – 4 Oct
4.98 out of 5 average rating, 222 reviews
Home in West Tisbury
West Tisbury Private Oasis
3 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in West Tisbury
3BR Home, Fenced Yard, Free use of car, Pets ok!
3 bedrooms, 6 beds, 2 bathrooms
22–27 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Aquinnah
MARTHA'S VINEYARD AQUINNAH OCEAN VIEW CLAY PIT RD
4 bedrooms, 7 beds, 4 bathrooms
19–25 Jul
4.84 out of 5 average rating, 25 reviews
Guest favourite
Place to stay in West Tisbury
Historical farmhouse on 87 acres
1 bedroom, 1 queen bed, 1 bathroom
20–25 Jul
4.8 out of 5 average rating, 5 reviews