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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
20–25 Sept
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4.99 out of 5 average rating, 111 reviews
Top guest favourite
Cottage in Chilmark
Walk to the beach: Charming Menemsha Cottage
5.0 out of 5 average rating, 63 reviews, 3 bedrooms, 4 beds, 3 bathrooms
5–12 Sept
Home in Chilmark
Charming North Road Retreat
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 5 beds, 4 bathrooms
9–16 Jul
Top guest favourite
Home in Chilmark
Fun, Authentic, Waterfront Cottage/air conditioned
4.98 out of 5 average rating, 44 reviews, 2 bedrooms, 4 beds, 1 bathroom
28 Sept – 3 Oct
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
Top guest favourite
Home in Chilmark
2 BR-Private guest house
4.98 out of 5 average rating, 90 reviews, 2 bedrooms, 2 beds, 1 bathroom
18–23 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
Beautiful Guest House in Chilmark
4.98 out of 5 average rating, 233 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Sept
Guest favourite
Home in Chilmark
Historic Brick Barn in Chilmark
4.98 out of 5 average rating, 55 reviews, 2 bedrooms, 3 beds, 1 bathroom
25–30 Jul
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
Top guest favourite
Home in Chilmark
Cool, Mid Century House -- Lucy Vincent Beach!
4.95 out of 5 average rating, 43 reviews, 4 bedrooms, 5 beds, 3 bathrooms
6–11 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
5–10 Jul
Guest favourite
Home in Chilmark
Secluded 3 bedroom home with private beach access
5.0 out of 5 average rating, 16 reviews, 4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
Guest favourite
Home in Aquinnah
Modern Aquinnah home close to the beach- 5 beds
4.95 out of 5 average rating, 20 reviews, 4 bedrooms, 5 beds, 2 bathrooms
26 Sept – 1 Oct
Top guest favourite
Cottage in West Tisbury
Cozy Cottage
4.96 out of 5 average rating, 76 reviews, 1 bedroom, 2 beds, 1 bathroom
26–31 Aug
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
Home in Chilmark
Tranquil Chilmark retreat
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 4 beds, 2 bathrooms
5–12 Jul
Guest favourite
Home in Chilmark
Private Hilltop Estate with tennis court
5.0 out of 5 average rating, 10 reviews, 4 bedrooms, 4 beds, 2.5 bathrooms
17–22 Jul
Guest favourite
Home in West Tisbury
Secluded and Serene Getaway
5.0 out of 5 average rating, 7 reviews, 5 bedrooms, 12 beds, 2 bathrooms
19–24 Sept