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Search results; Over 1,000 homes in Chilmark

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Top guest favourite
Home in Chilmark
The Blueberry House on Martha’s Vineyard
2 bedrooms, 2 beds, 2 private bathrooms
1–6 Sept
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5.0 out of 5 average rating, 28 reviews
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Top guest favourite
Cottage in Chilmark
Walk to the beach: Charming Menemsha Cottage
3 bedrooms, 4 beds, 3 bathrooms
14–21 Sept
5.0 out of 5 average rating, 68 reviews
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Superhost
Home in Chilmark
Evelyn's Menemsha Camp - Best Vineyard View
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.85 out of 5 average rating, 20 reviews
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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, 49 reviews
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Superhost
Home in Chilmark
Chilmark Cape in private wooded setting
4 bedrooms, 5 beds, 2 bathrooms
12–17 Sept
4.85 out of 5 average rating, 73 reviews
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Guest favourite
Home in Chilmark
Charming North Road Retreat
4 bedrooms, 5 beds, 4 bathrooms
1–6 Sept
5.0 out of 5 average rating, 6 reviews
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Home in West Tisbury
NEW Luxury Home: Aug/Sept Special
4 bedrooms, 5 beds, 3.5 bathrooms
8–13 Sept
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Top guest favourite
Home in Chilmark
Renovated Barn in Chilmark 3BR
3 bedrooms, 4 beds, 2 bathrooms
5–10 Oct
4.99 out of 5 average rating, 109 reviews
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Cottage in Chilmark
Charming Chilmark cottage with Atlantic view
2 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
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Home in Chilmark
Mid-Century Gem with Private Pool & Ocean Views
4 bedrooms, 2 bathrooms
29 Sept – 4 Oct
4.59 out of 5 average rating, 27 reviews
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Top guest favourite
Guest house in Chilmark
Beautiful Guest House in Chilmark
1 bedroom, 1 bed, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 245 reviews
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Guest favourite
Cottage in Chilmark
CHILMARK HILLTOP OCEAN VIEW
5 bedrooms, 5 beds, 2 bathrooms
6–11 Sept
4.86 out of 5 average rating, 21 reviews
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Guest favourite
Home in West Tisbury
Secluded and Serene Getaway
5 bedrooms, 12 beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Guest house in Chilmark
Beautifully Renovated 1800s Chilmark Barn
2 bedrooms, 3 beds, 1 bathroom
1–6 Sept
4.95 out of 5 average rating, 102 reviews
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Top guest favourite
Home in Chilmark
South House, Up-Island Living
3 bedrooms, 3 beds, 2 bathrooms
2–7 Sept
5.0 out of 5 average rating, 7 reviews
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Home in Aquinnah
Magical Tree House On Secluded End of Island
3 bedrooms, 3 beds, 1.5 bathrooms
19–24 Sept
4.83 out of 5 average rating, 24 reviews
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Home in Chilmark
Classic Chilmark Charm
7 bedrooms, 8 beds, 3.5 bathrooms
4–9 Sept
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Top guest favourite
Home in West Tisbury
Charming West Tisbury Home
5 bedrooms, 4 beds, 4.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 17 reviews
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Guest favourite
Home in Chilmark
Tucked away on Tea Lane, Chilmark
4 bedrooms, 8 beds, 2.5 bathrooms
1–8 Sept
5.0 out of 5 average rating, 25 reviews