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Search results; Over 1,000 homes in Chilmark

Guest favourite
Home in Chilmark
Cozy Waterfront Cottage, Newly Remodeled!
4 bedrooms, 4 beds, 2 private bathrooms
30 Aug – 6 Sept
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4.86 out of 5 average rating, 69 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, 235 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, 65 reviews
Top guest favourite
Guest house in West Tisbury
Vineyard Meadow Artist Studio
3 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 115 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, 98 reviews
Guest favourite
Guest suite in West Tisbury
The Abode Guest Suite. Private. Newly Renovated.
1 bed, 1 bathroom
13–18 Sept
4.95 out of 5 average rating, 128 reviews
Superhost
Cottage in Chilmark
Menemsha Inn Water View Cottage
1 bedroom, 2 beds, 1 bathroom
21–26 Jul
4.9 out of 5 average rating, 10 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, 45 reviews
Guest favourite
Home in Chilmark
Whalehall
3 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
4.8 out of 5 average rating, 5 reviews
Guest favourite
Guest suite in West Tisbury
Quiet West Tisbury 2 BDR Suite
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Jul
4.97 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
17–22 Jul
4.95 out of 5 average rating, 44 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, 90 reviews
Top guest favourite
Home in West Tisbury
Secluded Up Island Cottage
3 bedrooms, 3 beds, 1 bathroom
12–17 Nov
4.98 out of 5 average rating, 170 reviews
Superhost
Hotel in Chilmark
Wreath Bungalow @ Beach Plum Inn
1 bedroom, 1 bed, 1 bathroom
19–24 Jul
Guest favourite
Cottage in Chilmark
Vintage Chilmark Retreat
3 bedrooms, 5 beds, 2 bathrooms
21–26 Sept
4.95 out of 5 average rating, 40 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, 25 reviews
Superhost
Home in Chilmark
Evelyn's Menemsha Camp - Best Vineyard View
3 bedrooms, 4 beds, 2 bathrooms
18–23 Jul
4.85 out of 5 average rating, 20 reviews
Guest favourite
Guest suite in West Tisbury
Two Bedroom Suite on Retired Horse Farm
2 bedrooms, 2 queen beds, 1 bathroom
11–16 Jul
4.88 out of 5 average rating, 24 reviews
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