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Search results; Over 1,000 homes in Chilmark

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Top guest favourite
Home in Chilmark
Fun, Authentic, Waterfront Cottage/air conditioned
2 bedrooms, 4 beds, 1 private bathroom
5–10 Oct
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4.98 out of 5 average rating, 51 reviews
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Top guest favourite
Cottage in Chilmark
Walk to the beach: Charming Menemsha Cottage
3 bedrooms, 4 beds, 3 bathrooms
16–21 Sept
5.0 out of 5 average rating, 69 reviews
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Superhost
Home in Chilmark
Chilmark Cape in private wooded setting
4 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
4.85 out of 5 average rating, 74 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
Renovated Barn in Chilmark 3BR
3 bedrooms, 4 beds, 2 bathrooms
5–10 Oct
4.99 out of 5 average rating, 110 reviews
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Home in West Tisbury
NEW BUILD: A Love Letter to MV
4 bedrooms, 5 beds, 3.5 bathrooms
25–30 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Chilmark
The Blueberry House on Martha’s Vineyard
2 bedrooms, 2 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 29 reviews
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Top guest favourite
Home in Chilmark
South House, Up-Island Living
3 bedrooms, 3 beds, 2 bathrooms
16–23 Sept
5.0 out of 5 average rating, 8 reviews
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Top guest favourite
Guest house in Chilmark
Beautifully Renovated 1800s Chilmark Barn
2 bedrooms, 3 beds, 1 bathroom
24–29 Sept
4.95 out of 5 average rating, 103 reviews
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Guest favourite
Home in Chilmark
Quiet, Bright & Open MV home
4 bedrooms, 7 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 11 reviews
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Guest favourite
Home in Chilmark
Charming North Road Retreat
4 bedrooms, 5 beds, 4 bathrooms
17–22 Sept
5.0 out of 5 average rating, 7 reviews
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Home in Chilmark
Classic Chilmark Charm
7 bedrooms, 8 beds, 3.5 bathrooms
21–26 Sept
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Guest favourite
Home in West Tisbury
Tranquil & Private Waterfront Great Pond home
3 bedrooms, 4 beds, 3 bathrooms
12–19 Jun
4.97 out of 5 average rating, 32 reviews
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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, 230 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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Top guest favourite
Home in West Tisbury
Charming West Tisbury Home
5 bedrooms, 4 beds, 4.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 18 reviews
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Home in West Tisbury
New Waterfront Modern Farmhouse
4 bedrooms, 4 beds, 4.5 bathrooms
21–26 Sept
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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, 10 reviews
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Top guest favourite
Home in West Tisbury
Custom crafted Makonikey home
4 bedrooms, 2.5 bathrooms
16–21 Sept
5.0 out of 5 average rating, 10 reviews