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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, 50 reviews
Superhost
Room in Chilmark
Oceanview Inn Room (Single King or Double Queens)
1 king bed, 1 bathroom
13–18 Sept
New place to stay
Guest favourite
Home in Chilmark
Tucked away on Tea Lane, Chilmark
4 bedrooms, 8 beds, 2.5 bathrooms
6–13 Sept
5.0 out of 5 average rating, 25 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, 123 reviews
Guest favourite
Home in West Tisbury
Spacious, Private Cape in W. Tisbury
4 bedrooms, 6 beds, 3 bathrooms
14–21 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Chilmark
South House, Up-Island Living
3 bedrooms, 3 beds, 2 bathrooms
7–14 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Chilmark
Charming North Road Retreat
4 bedrooms, 5 beds, 4 bathrooms
8–13 Sept
5.0 out of 5 average rating, 7 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, 68 reviews
Guest favourite
Home in West Tisbury
New West Tisbury home
3 bedrooms, 3 beds, 2.5 bathrooms
8–13 Sept
4.84 out of 5 average rating, 25 reviews
Guest favourite
Home in West Tisbury
Light-filled Island Home
4 bedrooms, 5 beds, 3.5 bathrooms
7–12 Sept
4.95 out of 5 average rating, 20 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, 245 reviews
Top guest favourite
Home in West Tisbury
Charming West Tisbury Home
5 bedrooms, 4 beds, 4.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in West Tisbury
Vineyard Meadow Writer's Cottage with Hot Tub
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.97 out of 5 average rating, 63 reviews
Guest favourite
Home in Chilmark
Whalehall
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.86 out of 5 average rating, 7 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
27 Sept – 2 Oct
4.98 out of 5 average rating, 50 reviews
Guest favourite
Home in Chilmark
Tranquil Chilmark retreat
3 bedrooms, 4 beds, 2 bathrooms
13–20 Sept
5.0 out of 5 average rating, 5 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
Guest favourite
Guest suite in West Tisbury
The Apartment Guest Suite. Private. Just Renovated
1 queen bed, 1 bathroom
27 Sept – 2 Oct
4.95 out of 5 average rating, 137 reviews
Guest favourite
Home in West Tisbury
Sweet Spot in Heart of West Tisbury
3 bedrooms, 7 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 54 reviews