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Search results; Over 1,000 homes in Chilmark

Top guest favourite
Home in Chilmark
2 BR-Private guest house
2 bedrooms, 2 beds, 1 shared bathroom
18–23 Jul
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4.98 out of 5 average rating, 90 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
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
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
Guest favourite
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
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
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
Guest favourite
Home in Chilmark
Chilmark Cape in private wooded setting
4.85 out of 5 average rating, 68 reviews, 4 bedrooms, 5 beds, 2 bathrooms
31 Aug – 5 Sept
Home in Chilmark
Charming North Road Retreat
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 5 beds, 4 bathrooms
12–19 Jul
Top guest favourite
Guest house in Chilmark
Beautiful Guest House in Chilmark
4.98 out of 5 average rating, 235 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Sept
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
Home in West Tisbury
Up-Island Escape, Long Point Beach
4.98 out of 5 average rating, 222 reviews, 4 bedrooms, 6 beds, 3 bathrooms
16–21 Sept
Guest favourite
Home in Aquinnah
Modern Aquinnah home close to the beach- 5 beds
4.95 out of 5 average rating, 20 reviews, 4 bedrooms, 5 beds, 2 bathrooms
26 Sept – 1 Oct
Guest favourite
Home in West Tisbury
3BR Home, Fenced Yard, Free use of car, Pets ok!
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 6 beds, 2 bathrooms
19–24 Jul
Guest favourite
Home in West Tisbury
Renovated pond view home near Lamberts Cove beach
4.98 out of 5 average rating, 59 reviews, 4 bedrooms, 7 beds, 3 bathrooms
1–6 Aug
Home in Chilmark
Tranquil Chilmark retreat
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 4 beds, 2 bathrooms
12–19 Jul
Top guest favourite
Home in West Tisbury
Cozy 3BR Cottage with Lambert's Cove Beach access
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
6–11 Sept
Superhost
Home in West Tisbury
Private 5BR Vineyard Retreat - Peaceful & Central
4.93 out of 5 average rating, 15 reviews, 5 bedrooms, 8 beds, 2 bathrooms
26–31 Jul
Guest favourite
Place to stay in Aquinnah
Water View "Tower" Room on Martha's Vineyard
4.83 out of 5 average rating, 239 reviews, 1 bedroom, 1 bed, Toilet with sink
20–25 Sept