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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
11–16 Oct
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4.86 out of 5 average rating, 73 reviews
Guest favourite
Home in West Tisbury
Spacious, Private Cape in W. Tisbury
4 bedrooms, 6 beds, 3 bathrooms
15–22 Sept
5.0 out of 5 average rating, 7 reviews
Home in West Tisbury
Relaxing West Tisbury getaway - with pool!
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
Guest favourite
Home in West Tisbury
Light-filled Island Home
4 bedrooms, 5 beds, 3.5 bathrooms
19–24 Sept
4.95 out of 5 average rating, 20 reviews
Top guest favourite
Home in Chilmark
South House, Up-Island Living
3 bedrooms, 3 beds, 2 bathrooms
14–21 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in West Tisbury
Waterfront home with key to private Quansoo Beach
4 bedrooms, 6 beds, 2.5 bathrooms
14–21 Sept
4.93 out of 5 average rating, 15 reviews
Top guest favourite
Guest house in West Tisbury
Vineyard Meadow Artist Studio
3 beds, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 124 reviews
Top guest favourite
Home in West Tisbury
Beloved 5-bedroom with fenced in yard and hot tub
5 bedrooms, 8 beds, 3 bathrooms
13–20 Sept
5.0 out of 5 average rating, 14 reviews
Superhost
Room in Chilmark
Oceanview Inn Room (Single King or Double Queens)
1 king bed, 1 bathroom
20–25 Sept
New place to stay
Top guest favourite
Cottage in Chilmark
Walk to the beach: Charming Menemsha Cottage
3 bedrooms, 4 beds, 3 bathrooms
14–19 Sept
5.0 out of 5 average rating, 68 reviews
Top guest favourite
Home in West Tisbury
Charming West Tisbury Home
5 bedrooms, 4 beds, 4.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Home in Chilmark
Tucked away on Tea Lane, Chilmark
4 bedrooms, 8 beds, 2.5 bathrooms
13–20 Sept
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Guest house in Chilmark
Beautiful Guest House in Chilmark
1 bedroom, 1 bed, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 246 reviews
Guest favourite
Home in West Tisbury
West Tisbury Privacy! Lambert’s Cove Beach Access.
3 bedrooms, 4 beds, 1.5 bathrooms
13–18 Sept
4.87 out of 5 average rating, 55 reviews
Guest favourite
Home in Chilmark
Tranquil Chilmark retreat
3 bedrooms, 4 beds, 2 bathrooms
20–27 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in West Tisbury
Vineyard Meadow Writer's Cottage with Hot Tub
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
4.97 out of 5 average rating, 64 reviews
Guest favourite
Home in Chilmark
Charming North Road Retreat
4 bedrooms, 5 beds, 4 bathrooms
15–20 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in West Tisbury
Sweet Spot in Heart of West Tisbury
3 bedrooms, 7 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 54 reviews
Home in West Tisbury
Summer Beach Pass: Wooded Martha's Vineyard Escape
3 bedrooms, 5 beds, 2 bathrooms
14–21 Sept