Search results; Over 1,000 homes in Chilmark

Top guest favourite
Home in Chilmark
Renovated Barn in Chilmark 3BR
3 bedrooms, 4 beds, 2 private bathrooms
22–29 Aug
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4.99 out of 5 average rating, 106 reviews
Top guest favourite
Cottage in Chilmark
Walk to the beach: Charming Menemsha Cottage
5.0 out of 5 average rating, 63 reviews, 3 bedrooms, 4 beds, 3 bathrooms
5–12 Sept
Home in Chilmark
Charming North Road Retreat
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 5 beds, 4 bathrooms
9–16 Jul
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
Chilmark Cape in private wooded setting
4.85 out of 5 average rating, 68 reviews, 4 bedrooms, 5 beds, 2 bathrooms
5–10 Jul
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
Home in Chilmark
Fun, Authentic, Waterfront Cottage/air conditioned
4.98 out of 5 average rating, 44 reviews, 2 bedrooms, 4 beds, 1 bathroom
28 Sept – 3 Oct
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
Top guest favourite
Home in Chilmark
Cool, Mid Century House -- Lucy Vincent Beach!
4.95 out of 5 average rating, 43 reviews, 4 bedrooms, 5 beds, 3 bathrooms
6–11 Jul
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
Guest house in Chilmark
Beautiful Guest House in Chilmark
4.98 out of 5 average rating, 233 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Sept
Guest favourite
Cottage in Chilmark
Menemsha Ocean View Cottage. Lucy Beach Passes
4.88 out of 5 average rating, 8 reviews, 1 bedroom, 2 beds, 1 bathroom
7–12 Jul
Home in Chilmark
Cozy house on private beach
1 bedroom, 2 beds, 1 bathroom
25 Aug – 1 Sept
Guest favourite
Home in Chilmark
Historic Brick Barn in Chilmark
4.98 out of 5 average rating, 55 reviews, 2 bedrooms, 3 beds, 1 bathroom
25–30 Jul
Guest favourite
Cottage in Chilmark
Vintage Chilmark Retreat
4.95 out of 5 average rating, 39 reviews, 3 bedrooms, 5 beds, 2 bathrooms
21–26 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
5–10 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
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
28 Sept – 4 Oct
Guest favourite
Home in West Tisbury
Private 5BR Vineyard Retreat - Peaceful & Central
4.93 out of 5 average rating, 14 reviews, 5 bedrooms, 8 beds, 2 bathrooms
26–31 Jul