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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, 113 reviews
Top guest favourite
Guest house in Chilmark
Beautiful Guest House in Chilmark
4.98 out of 5 average rating, 238 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Sept
Top guest favourite
Guest house in Chilmark
Beautifully Renovated 1800s Chilmark Barn
4.95 out of 5 average rating, 99 reviews, 2 bedrooms, 3 beds, 1 bathroom
1–6 Sept
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Home in Chilmark
The Blueberry House on Martha’s Vineyard
5.0 out of 5 average rating, 27 reviews, 2 bedrooms, 2 beds, 2 bathrooms
30 Aug – 4 Sept
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Cottage in Chilmark
Walk to the beach: Charming Menemsha Cottage
5.0 out of 5 average rating, 66 reviews, 3 bedrooms, 4 beds, 3 bathrooms
5–12 Sept
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Home in Chilmark
Fun, Authentic, Waterfront Cottage/air conditioned
4.98 out of 5 average rating, 46 reviews, 2 bedrooms, 4 beds, 1 bathroom
28 Sept – 3 Oct
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Guest suite in West Tisbury
The Studio Guest Suite. Private. Newly Renovated.
4.92 out of 5 average rating, 166 reviews, 1 bed, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Home in Aquinnah
MARTHA'S VINEYARD AQUINNAH OCEAN VIEW CLAY PIT RD
4.84 out of 5 average rating, 25 reviews, 4 bedrooms, 7 beds, 4 bathrooms
1–7 Aug
Superhost
Hotel in Chilmark
Sage Room @The Beach Plum Inn
4.75 out of 5 average rating, 4 reviews, 1 bedroom, 1 bed, 1 bathroom
17–22 Aug
Guest favourite
Place to stay in Aquinnah
Water View "Tower" Room on Martha's Vineyard
4.83 out of 5 average rating, 241 reviews, 1 bedroom, 1 bed, WC
20–25 Sept
Guest favourite
Cottage in Chilmark
Menemsha Ocean View Cottage. Lucy Beach Passes
4.9 out of 5 average rating, 10 reviews, 1 bedroom, 2 beds, 1 bathroom
16–21 Aug
Cottage in Chilmark
Charming Chilmark cottage with Atlantic view
2 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
Guest favourite
Home in West Tisbury
Cozy 3BR Cottage with Lambert's Cove Beach access
4.88 out of 5 average rating, 8 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
6–11 Sept
Guest favourite
Home in Aquinnah
Secluded Aquinnah Cottage
4.83 out of 5 average rating, 18 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Oct
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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
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Home in Chilmark
Charming Chilmark Cottage
4.98 out of 5 average rating, 43 reviews, 1 bedroom, 2 beds, No bathroom
13–20 Sept
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Home in Chilmark
Peaceful Retreat Near Up-Island Beaches
4.98 out of 5 average rating, 91 reviews, 2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
Guest favourite
Home in Chilmark
Whalehall
4.8 out of 5 average rating, 5 reviews, 3 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
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