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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, 110 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, 61 reviews
Home in Chilmark
Charming North Road Retreat
4 bedrooms, 5 beds, 4 bathrooms
9–16 Jul
5.0 out of 5 average rating, 3 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, 233 reviews
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, 24 reviews
Guest favourite
Home in Chilmark
Secluded 3 bedroom home with private beach access
4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Chilmark
2 BR-Private guest house
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Jul
4.98 out of 5 average rating, 88 reviews
Top guest favourite
Home in Chilmark
Cool, Mid Century House -- Lucy Vincent Beach!
4 bedrooms, 5 beds, 3 bathrooms
6–11 Jul
4.95 out of 5 average rating, 43 reviews
Guest favourite
Home in Chilmark
The Charming Cove House
3 bedrooms, 4 beds, 1.5 bathrooms
11–18 Jul
4.95 out of 5 average rating, 19 reviews
Top guest favourite
Guest house in Chilmark
Beautifully Renovated 1800s Chilmark Barn
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
4.95 out of 5 average rating, 99 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, 43 reviews
Guest favourite
Home in Chilmark
Historic Brick Barn in Chilmark
2 bedrooms, 3 beds, 1 bathroom
25–30 Jul
4.98 out of 5 average rating, 55 reviews
Home in Chilmark
Tranquil Chilmark retreat
3 bedrooms, 4 beds, 2 bathrooms
5–12 Jul
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Chilmark
Chilmark Cape in private wooded setting
4 bedrooms, 5 beds, 2 bathrooms
5–10 Jul
4.85 out of 5 average rating, 68 reviews
Guest favourite
Cottage in Chilmark
CHILMARK HILLTOP OCEAN VIEW
5 bedrooms, 5 beds, 2 bathrooms
1–6 Jul
4.84 out of 5 average rating, 19 reviews
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
Guest favourite
Home in Chilmark
Path to Menemsha Beach
1 bedroom, 1 bed, 1 bathroom
1–6 Jul
4.88 out of 5 average rating, 8 reviews
Top guest favourite
Home in West Tisbury
Vineyard Meadow Writer's Cottage with Hot Tub
3 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
4.97 out of 5 average rating, 58 reviews
Guest favourite
Home in Chilmark
Private Hilltop Estate with tennis court
4 bedrooms, 4 beds, 2.5 bathrooms
17–22 Jul
5.0 out of 5 average rating, 10 reviews