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Search results; Over 1,000 homes in Chilmark

Top guest favourite
Home in Chilmark
Fun, Authentic, Waterfront Cottage/air conditioned
2 bedrooms, 4 beds, 1 private bathroom
5–10 Oct
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4.98 out of 5 average rating, 51 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
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
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, 69 reviews
Superhost
Hotel in Chilmark
Oceanview Inn Room (Single King or Double Queens)
1 bedroom, 1 king bed, 1 bathroom
20–25 Sept
New place to stay
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 West Tisbury
Secluded Up Island Cottage
3 bedrooms, 3 beds, 1 bathroom
2–7 Oct
4.98 out of 5 average rating, 170 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 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
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
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 Aquinnah
Amazing Views!!Sunsets!!HistoricMV Gem&Lg.RoofDeck
3 bedrooms, 5 beds, 2 bathrooms
16–21 Oct
4.89 out of 5 average rating, 54 reviews
Top guest favourite
Guest house in Chilmark
Beautiful Guest House in Chilmark
1 bedroom, 1 bed, 1 bathroom
14–19 Sept
4.98 out of 5 average rating, 247 reviews
Guest favourite
Home in West Tisbury
Secluded and Serene Getaway
5 bedrooms, 12 beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Room in West Tisbury
warm and spacious B and B in our Martha's Vin home
1 queen bed, 1 bathroom
25–30 Sept
4.98 out of 5 average rating, 52 reviews
Home in West Tisbury
Summer Beach Pass: Wooded Martha's Vineyard Escape
3 bedrooms, 5 beds, 2 bathrooms
14–21 Sept