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Search results; Over 1,000 homes in Chilmark

Top guest favourite
Guest house in Chilmark
Beautiful Guest House in Chilmark
1 bedroom, 1 bed, 1 private bathroom
2–7 Sept
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4.98 out of 5 average rating, 235 reviews
Top guest favourite
Cottage in Chilmark
Walk to the beach: Charming Menemsha Cottage
5.0 out of 5 average rating, 65 reviews, 3 bedrooms, 4 beds, 3 bathrooms
5–12 Sept
Top guest favourite
Home in Chilmark
Fun, Authentic, Waterfront Cottage/air conditioned
4.98 out of 5 average rating, 45 reviews, 2 bedrooms, 4 beds, 1 bathroom
28 Sept – 3 Oct
Home in Chilmark
Charming North Road Retreat
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 5 beds, 4 bathrooms
13–18 Jul
Top guest favourite
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
Top guest favourite
Guest house in Chilmark
Beautifully Renovated 1800s Chilmark Barn
4.95 out of 5 average rating, 98 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
Top guest favourite
Home in Chilmark
2 BR-Private guest house
4.98 out of 5 average rating, 90 reviews, 2 bedrooms, 2 beds, 1 bathroom
18–23 Jul
Guest favourite
Home in Chilmark
Cozy Waterfront Cottage, Newly Remodeled!
4.86 out of 5 average rating, 69 reviews, 4 bedrooms, 4 beds, 2 bathrooms
30 Aug – 6 Sept
Guest favourite
Home in Chilmark
The Blueberry House on Martha’s Vineyard
5.0 out of 5 average rating, 25 reviews, 2 bedrooms, 2 beds, 2 bathrooms
30 Aug – 4 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
Top guest favourite
Home in Chilmark
Cool, Mid Century House -- Lucy Vincent Beach!
4.95 out of 5 average rating, 44 reviews, 4 bedrooms, 5 beds, 3 bathrooms
17–22 Jul
Home in Chilmark
The Charming Cove House
4.95 out of 5 average rating, 19 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
30 Aug – 6 Sept
Home in Chilmark
Mid-Century Gem with Private Pool & Ocean Views
4.56 out of 5 average rating, 25 reviews, 4 bedrooms, 2 bathrooms
30 Aug – 4 Sept
Guest favourite
Home in West Tisbury
Tranquil & Private Waterfront Great Pond home
4.96 out of 5 average rating, 28 reviews, 3 bedrooms, 4 beds, 3 bathrooms
21–28 Sept
Guest favourite
Home in West Tisbury
Sanctuary House: An ocean-view farmhouse retreat
4.96 out of 5 average rating, 26 reviews, 4 bedrooms, 5 beds, 2 bathrooms
5–10 Sept
Guest favourite
Home in Chilmark
Private Hilltop Estate with tennis court
5.0 out of 5 average rating, 10 reviews, 4 bedrooms, 4 beds, 2.5 bathrooms
21–26 Jul
Guest favourite
Home in Aquinnah
Peaceful Water-View Home with Large Deck & Balcony
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
30 Aug – 4 Sept
Superhost
Home in West Tisbury
Private 5BR Vineyard Retreat - Peaceful & Central
4.94 out of 5 average rating, 16 reviews, 5 bedrooms, 8 beds, 2 bathrooms
26 Sept – 1 Oct
Guest favourite
Home in Chilmark
Quiet, Bright & Open MV home
5.0 out of 5 average rating, 7 reviews, 4 bedrooms, 7 beds, 2 bathrooms
6–11 Sept