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Search results; Over 1,000 homes in Chilmark

Guest favourite
Home in Chilmark
Cozy Waterfront Cottage, Newly Remodeled!
4 bedrooms, 4 beds, 2 private bathrooms
30 Aug – 6 Sept
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4.86 out of 5 average rating, 69 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
Cool, Mid Century House -- Lucy Vincent Beach!
4 bedrooms, 5 beds, 3 bathrooms
17–22 Jul
4.95 out of 5 average rating, 44 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, 45 reviews
Guest favourite
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
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
Top guest favourite
Home in Chilmark
2 BR-Private guest house
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Jul
4.98 out of 5 average rating, 90 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
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
Guest favourite
Home in Aquinnah
Modern Aquinnah home close to the beach- 5 beds
4 bedrooms, 5 beds, 2 bathrooms
26 Sept – 1 Oct
4.95 out of 5 average rating, 20 reviews
Home in Chilmark
Charming North Road Retreat
4 bedrooms, 5 beds, 4 bathrooms
11–18 Jul
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
19–24 Jul
5.0 out of 5 average rating, 9 reviews
Home in Chilmark
Tranquil Chilmark retreat
3 bedrooms, 4 beds, 2 bathrooms
12–19 Jul
5.0 out of 5 average rating, 4 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, 235 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 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
Guest favourite
Home in West Tisbury
Renovated pond view home near Lamberts Cove beach
4 bedrooms, 7 beds, 3 bathrooms
1–6 Aug
4.98 out of 5 average rating, 59 reviews
Guest favourite
Home in West Tisbury
Sanctuary House: An ocean-view farmhouse retreat
4 bedrooms, 5 beds, 2 bathrooms
5–10 Sept
4.96 out of 5 average rating, 26 reviews
Guest favourite
Home in West Tisbury
Martha’s Vineyard Farmhouse
4 bedrooms, 6 beds, 2 bathrooms
18–25 Jul
5.0 out of 5 average rating, 5 reviews