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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
Beautifully Renovated 1800s Chilmark Barn
2 bedrooms, 3 beds, 1 bathroom
1–6 Sept
4.95 out of 5 average rating, 99 reviews
Top guest favourite
Guest house in Chilmark
Beautiful Guest House in Chilmark
1 bedroom, 1 bed, 1 bathroom
2–7 Sept
4.98 out of 5 average rating, 238 reviews
Top guest favourite
Cottage in Chilmark
Walk to the beach: Charming Menemsha Cottage
3 bedrooms, 4 beds, 3 bathrooms
5–12 Sept
5.0 out of 5 average rating, 66 reviews
Top guest favourite
Home in Chilmark
The Blueberry House on Martha’s Vineyard
2 bedrooms, 2 beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 27 reviews
Guest favourite
Cottage in Chilmark
Menemsha Ocean View Cottage. Lucy Beach Passes
1 bedroom, 2 beds, 1 bathroom
16–21 Aug
4.9 out of 5 average rating, 10 reviews
Superhost
Hotel in Chilmark
Sage Room @The Beach Plum Inn
1 bedroom, 1 bed, 1 bathroom
17–22 Aug
4.75 out of 5 average rating, 4 reviews
Guest favourite
Place to stay in Aquinnah
Water View "Tower" Room on Martha's Vineyard
1 bedroom, 1 bed, WC
20–25 Sept
4.83 out of 5 average rating, 241 reviews
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, 47 reviews
Top guest favourite
Guest suite in West Tisbury
The Studio Guest Suite. Private. Newly Renovated.
1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.92 out of 5 average rating, 166 reviews
Guest favourite
Home in West Tisbury
Vineyard Meadow Writer's Cottage with Hot Tub
3 bedrooms, 4 beds, 2 bathrooms
4–9 Sept
4.97 out of 5 average rating, 61 reviews
Superhost
Home in Chilmark
Evelyn's Menemsha Camp - Best Vineyard View
3 bedrooms, 4 beds, 2 bathrooms
29 Aug – 3 Sept
4.85 out of 5 average rating, 20 reviews
Guest favourite
Home in Aquinnah
Secluded Aquinnah Cottage
1 bedroom, 1 queen bed, 1 bathroom
1–6 Oct
4.83 out of 5 average rating, 18 reviews
Guest favourite
Home in Aquinnah
MARTHA'S VINEYARD AQUINNAH OCEAN VIEW CLAY PIT RD
4 bedrooms, 7 beds, 4 bathrooms
1–7 Aug
4.84 out of 5 average rating, 25 reviews
Cottage in Chilmark
Charming Chilmark cottage with Atlantic view
2 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
Top guest favourite
Home in Chilmark
Renovated Barn in Chilmark 3BR
3 bedrooms, 4 beds, 2 bathrooms
22–29 Aug
4.99 out of 5 average rating, 106 reviews
Top guest favourite
Home in Chilmark
Peaceful Retreat Near Up-Island Beaches
2 bedrooms, 2 queen beds, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 91 reviews
Cottage in Aquinnah
Aquinnah beach cottage
3 bedrooms, 5 beds, 1 bathroom
19–25 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Chilmark
Charming Chilmark Cottage
1 bedroom, 2 beds, No bathroom
13–20 Sept
4.98 out of 5 average rating, 43 reviews