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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, 116 reviews
Top guest favourite
Cottage in Chilmark
Walk to the beach: Charming Menemsha Cottage
3 bedrooms, 4 beds, 3 bathrooms
16–21 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
Top guest favourite
Guest house in Chilmark
Beautiful Guest House in Chilmark
1 bedroom, 1 bed, 1 bathroom
16–21 Sept
4.98 out of 5 average rating, 247 reviews
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
Guest house in West Tisbury
Vineyard Meadow Artist Studio
3 beds, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 125 reviews
Top guest favourite
Guest house in Chilmark
Beautifully Renovated 1800s Chilmark Barn
2 bedrooms, 3 beds, 1 bathroom
24–29 Sept
4.95 out of 5 average rating, 103 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
Guest favourite
Home in West Tisbury
Spacious, Private Cape in W. Tisbury
4 bedrooms, 6 beds, 3 bathrooms
17–24 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
16–21 Sept
Guest favourite
Home in Chilmark
Bayberry Cottage- Menemsha Inn & Lucy
1 bedroom, 2 beds, 1 bathroom
26 Sept – 1 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Chilmark
South House, Up-Island Living
3 bedrooms, 3 beds, 2 bathrooms
16–23 Sept
5.0 out of 5 average rating, 8 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
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
Guest favourite
Home in West Tisbury
New West Tisbury home
3 bedrooms, 3 beds, 2.5 bathrooms
17–22 Sept
4.84 out of 5 average rating, 25 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
Home in West Tisbury
Vineyard Meadow Writer's Cottage with Hot Tub
3 bedrooms, 4 beds, 2 bathrooms
16–21 Sept
4.97 out of 5 average rating, 64 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, 18 reviews
Top guest favourite
Home in Chilmark
Peaceful Retreat Near Up-Island Beaches
2 bedrooms, 2 queen beds, 1 bathroom
4–9 Oct
4.98 out of 5 average rating, 95 reviews