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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

20–25 Sept

$2,061 SGD for 5 nights

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4.99 out of 5 average rating, 113 reviews

Top guest favourite

Home in Chilmark

Fun, Authentic, Waterfront Cottage/air conditioned

2 bedrooms, 4 beds, 1 bathroom

28 Sept – 3 Oct

$4,901 SGD for 5 nights

4.98 out of 5 average rating, 48 reviews

Top guest favourite

Cottage in Chilmark

Walk to the beach: Charming Menemsha Cottage

3 bedrooms, 4 beds, 3 bathrooms

5–12 Sept

5.0 out of 5 average rating, 66 reviews

Top guest favourite

Home in Chilmark

Renovated Barn in Chilmark 3BR

3 bedrooms, 4 beds, 2 bathrooms

22–29 Aug

$6,863 SGD for 7 nights

4.99 out of 5 average rating, 106 reviews

Superhost

Home in Chilmark

Evelyn's Menemsha Camp - Best Vineyard View

3 bedrooms, 4 beds, 2 bathrooms

29 Aug – 3 Sept

$6,305 SGD for 5 nights

4.85 out of 5 average rating, 20 reviews

Top guest favourite

Home in Chilmark

The Blueberry House on Martha’s Vineyard

2 bedrooms, 2 beds, 2 bathrooms

30 Aug – 4 Sept

$4,325 SGD for 5 nights

5.0 out of 5 average rating, 27 reviews

Home in Chilmark

Mid-Century Gem with Private Pool & Ocean Views

4 bedrooms, 2 bathrooms

27 Aug – 1 Sept

$7,512 SGD for 5 nights

4.56 out of 5 average rating, 25 reviews

Guest favourite

Home in Chilmark

Charming North Road Retreat

4 bedrooms, 5 beds, 4 bathrooms

31 Aug – 7 Sept

$7,213 SGD for 7 nights

5.0 out of 5 average rating, 5 reviews

Top guest favourite

Home in Chilmark

Peaceful Retreat Near Up-Island Beaches

2 bedrooms, 2 queen beds, 1 bathroom

20–25 Sept

$3,123 SGD for 5 nights

4.98 out of 5 average rating, 91 reviews

Guest favourite

Home in Chilmark

Chilmark Cape in private wooded setting

4 bedrooms, 5 beds, 2 bathrooms

31 Aug – 5 Sept

$4,535 SGD for 5 nights

4.85 out of 5 average rating, 68 reviews

Top guest favourite

Home in Chilmark

Cool, Mid Century House -- Lucy Vincent Beach!

4 bedrooms, 5 beds, 3 bathrooms

24–29 Aug

$15,328 SGD for 5 nights

4.95 out of 5 average rating, 44 reviews

Top guest favourite

Guest house in Chilmark

Beautifully Renovated 1800s Chilmark Barn

2 bedrooms, 3 beds, 1 bathroom

1–6 Sept

$2,427 SGD for 5 nights

4.95 out of 5 average rating, 99 reviews

Guest favourite

Home in West Tisbury

Sanctuary House: An ocean-view farmhouse retreat

4 bedrooms, 5 beds, 2 bathrooms

5–10 Sept

$6,475 SGD for 5 nights

4.96 out of 5 average rating, 27 reviews

Guest favourite

Home in West Tisbury

Martha’s Vineyard Farmhouse

4 bedrooms, 6 beds, 2 bathrooms

22–29 Aug

$13,530 SGD for 7 nights

5.0 out of 5 average rating, 5 reviews

Top guest favourite

Guest house in Chilmark

Beautiful Guest House in Chilmark

1 bedroom, 1 bed, 1 bathroom

2–7 Sept

$2,646 SGD for 5 nights

4.98 out of 5 average rating, 238 reviews

Home in Chilmark

Secluded 3 bedroom home with private beach access

4 bedrooms, 5 beds, 2 bathrooms

20–25 Sept

$5,193 SGD for 5 nights

5.0 out of 5 average rating, 16 reviews

Home in Chilmark

Great screen porch and fun house

4 bedrooms, 6 beds, 2 bathrooms

20–26 Sept

$5,367 SGD for 6 nights

Guest favourite

Home in Chilmark

Private Hilltop Estate with tennis court

4 bedrooms, 4 beds, 2.5 bathrooms

4–9 Aug

$20,262 SGD for 5 nights

5.0 out of 5 average rating, 11 reviews

Top guest favourite

Home in West Tisbury

3BR Home, Fenced Yard, Free use of car, Pets ok!

3 bedrooms, 6 beds, 2 bathrooms

26–31 Aug

$6,038 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 11 reviews