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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, 65 reviews, 3 bedrooms, 4 beds, 3 bathrooms
5–12 Sept
Top guest favourite
Home in Chilmark
Fun, Authentic, Waterfront Cottage/air conditioned
4.98 out of 5 average rating, 45 reviews, 2 bedrooms, 4 beds, 1 bathroom
28 Sept – 3 Oct
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
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
17–22 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
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
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
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
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
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 Chilmark
Renovated Barn in Chilmark 3BR
4.99 out of 5 average rating, 106 reviews, 3 bedrooms, 4 beds, 2 bathrooms
22–29 Aug
Superhost
Home in Oak Bluffs
NEW! Charming Oak Bluffs Cottage - Sleeps 8
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
8–13 Jul
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
Guest favourite
Home in West Tisbury
Martha’s Vineyard Farmhouse
5.0 out of 5 average rating, 5 reviews, 4 bedrooms, 6 beds, 2 bathrooms
11–18 Jul
Home in West Tisbury
Summer Beach Pass: Wooded Martha's Vineyard Escape
3 bedrooms, 5 beds, 2 bathrooms
11–18 Jul
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
Tranquil & Private Waterfront Great Pond home
4.96 out of 5 average rating, 28 reviews, 3 bedrooms, 4 beds, 3 bathrooms
21–28 Sept
Guest favourite
Home in Chilmark
Path to Menemsha Beach
4.88 out of 5 average rating, 8 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Jul