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Search results; Over 1,000 homes in Chilmark

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Top guest favourite
Guest house in Chlmark
4-Season Guest House on Historic Chilmark Estate
1 bedroom, 1 bed, 1 private bathroom
19–24 Sept
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4.99 out of 5 average rating, 116 reviews
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Top guest favourite
Home in Chilmark
Fun, Authentic, Waterfront Cottage/air conditioned
2 bedrooms, 4 beds, 1 bathroom
5–10 Oct
4.98 out of 5 average rating, 51 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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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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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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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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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
Guest house in Chilmark
Beautiful Guest House in Chilmark
1 bedroom, 1 bed, 1 bathroom
19–24 Sept
4.98 out of 5 average rating, 247 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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Superhost
Home in West Tisbury
Private 5BR Vineyard Retreat - Peaceful & Central
5 bedrooms, 8 beds, 2 bathrooms
19–24 Oct
4.89 out of 5 average rating, 18 reviews
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Top guest favourite
Home in Chilmark
Historic Brick Barn in Chilmark
2 bedrooms, 3 beds, 1 bathroom
6–11 Jun
4.98 out of 5 average rating, 60 reviews
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Guest favourite
Home in West Tisbury
1800s Farmhouse | Sanctuary Trails | Pickleball
5 bedrooms, 8 beds, 3.5 bathrooms
22–27 Sept
4.93 out of 5 average rating, 15 reviews
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Guest favourite
Cottage in Chilmark
CHILMARK HILLTOP OCEAN VIEW
5 bedrooms, 5 beds, 2 bathrooms
26 Sept – 1 Oct
4.86 out of 5 average rating, 21 reviews
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Guest favourite
Home in Chilmark
Charming North Road Retreat
4 bedrooms, 5 beds, 4 bathrooms
21–26 Sept
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Home in Chilmark
Peaceful Retreat Near Up-Island Beaches
2 bedrooms, 2 queen beds, 1 bathroom
4–9 Oct
4.98 out of 5 average rating, 95 reviews
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Guest favourite
Home in Aquinnah
Amazing Views!!Sunsets!!HistoricMV Gem&Lg.RoofDeck
3 bedrooms, 5 beds, 2 bathrooms
16–21 Oct
4.89 out of 5 average rating, 54 reviews
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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 Chilmark
South House, Up-Island Living
3 bedrooms, 3 beds, 2 bathrooms
20–27 Sept
5.0 out of 5 average rating, 8 reviews