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Search results; Over 1,000 homes in Chilmark

Top guest favourite
Guest house in Chlmark
4-Season Guest House on Historic Chilmark Estate
1 bedroom, 1 bed, 1 private bathroom
19–24 Sept
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4.99 out of 5 average rating, 115 reviews
Superhost
Room in Chilmark
Oceanview Inn Room (Single King or Double Queens)
1 king bed, 1 bathroom
6–11 Sept
New place to stay
Top guest favourite
Cottage in Chilmark
Walk to the beach: Charming Menemsha Cottage
3 bedrooms, 4 beds, 3 bathrooms
14–21 Sept
5.0 out of 5 average rating, 68 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 Chilmark
Fun, Authentic, Waterfront Cottage/air conditioned
2 bedrooms, 4 beds, 1 bathroom
28 Sept – 3 Oct
4.98 out of 5 average rating, 50 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
Featured hotel
Room in Oak Bluffs
King deluxe
1 king bed, 1 bathroom
11–16 Oct
Superhost
Home in Chilmark
Evelyn's Menemsha Camp - Best Vineyard View
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.85 out of 5 average rating, 20 reviews
Top guest favourite
Home in West Tisbury
Charming West Tisbury Home
5 bedrooms, 4 beds, 4.5 bathrooms
4–9 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Guest house in West Tisbury
The Artist’s studio near Long Point Beach
1 bedroom, 2 beds, 1 bathroom
16–21 Oct
4.89 out of 5 average rating, 189 reviews
Top guest favourite
Guest house in Chilmark
Beautifully Renovated 1800s Chilmark Barn
2 bedrooms, 3 beds, 1 bathroom
3–8 Sept
4.95 out of 5 average rating, 103 reviews
Guest favourite
Home in West Tisbury
Light-filled Island Home
4 bedrooms, 5 beds, 3.5 bathrooms
3–8 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
1–6 Oct
4.98 out of 5 average rating, 170 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
Cottage in West Tisbury
Cozy Cottage
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
4.95 out of 5 average rating, 85 reviews
Guest favourite
Home in Chilmark
Charming North Road Retreat
4 bedrooms, 5 beds, 4 bathrooms
4–9 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Chilmark
Bayberry Cottage- Menemsha Inn & Lucy
1 bedroom, 2 beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 5 reviews
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, 62 reviews
Top guest favourite
Home in Chilmark
South House, Up-Island Living
3 bedrooms, 3 beds, 2 bathrooms
3–10 Sept
5.0 out of 5 average rating, 8 reviews