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Search results; Over 1,000 homes in Chilmark

Top guest favourite
Cottage in Chilmark
Vintage Chilmark Retreat
3 bedrooms, 5 beds, 2 bathrooms
21–26 Sept
,
4.95 out of 5 average rating, 44 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
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
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
Light-filled Island Home
4 bedrooms, 5 beds, 3.5 bathrooms
9–14 Sept
4.95 out of 5 average rating, 20 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
Featured hotel
Hotel in Oak Bluffs
King
1 bedroom, 1 king bed, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Chilmark
South House, Up-Island Living
3 bedrooms, 3 beds, 2 bathrooms
9–16 Sept
5.0 out of 5 average rating, 8 reviews
Home in Aquinnah
Magical Tree House On Secluded End of Island
3 bedrooms, 3 beds, 1.5 bathrooms
19–24 Sept
4.83 out of 5 average rating, 24 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
Guest favourite
Home in West Tisbury
New West Tisbury home
3 bedrooms, 3 beds, 2.5 bathrooms
10–15 Sept
4.84 out of 5 average rating, 25 reviews
Top guest favourite
Home in Chilmark
Fun, Authentic, Waterfront Cottage/air conditioned
2 bedrooms, 4 beds, 1 bathroom
5–10 Oct
4.98 out of 5 average rating, 51 reviews
Top guest favourite
Guest house in Chilmark
Beautifully Renovated 1800s Chilmark Barn
2 bedrooms, 3 beds, 1 bathroom
9–14 Sept
4.95 out of 5 average rating, 103 reviews
Top guest favourite
Home in Aquinnah
Oceanview Beachwalk Cottage
1 bedroom, 2 beds, 1 bathroom
28 Sept – 4 Oct
4.93 out of 5 average rating, 67 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, 51 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, 190 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 West Tisbury
Sweet Spot in Heart of West Tisbury
3 bedrooms, 7 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 54 reviews
Top guest favourite
Home in Chilmark
The Blueberry House on Martha’s Vineyard
2 bedrooms, 2 beds, 2 bathrooms
10–15 Sept
5.0 out of 5 average rating, 28 reviews