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Search results; Over 1,000 homes in Chilmark

Superhost

Home in Chilmark

Evelyn's Menemsha Camp - Best Vineyard View

3 bedrooms, 4 beds, 2 private bathrooms

20–25 Sept

$5,338 SGD for 5 nights

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4.85 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

14–21 Sept

5.0 out of 5 average rating, 66 reviews

Top guest favourite

Home in Chilmark

Fun, Authentic, Waterfront Cottage/air conditioned

2 bedrooms, 4 beds, 1 bathroom

28 Sept – 3 Oct

$4,885 SGD for 5 nights

4.98 out of 5 average rating, 48 reviews

Top guest favourite

Home in Chilmark

The Blueberry House on Martha’s Vineyard

2 bedrooms, 2 beds, 2 bathrooms

30 Aug – 4 Sept

$4,313 SGD for 5 nights

5.0 out of 5 average rating, 27 reviews

Top guest favourite

Home in Chilmark

Renovated Barn in Chilmark 3BR

3 bedrooms, 4 beds, 2 bathrooms

22–29 Aug

$6,844 SGD for 7 nights

4.99 out of 5 average rating, 106 reviews

Guest favourite

Home in Chilmark

Chilmark Cape in private wooded setting

4 bedrooms, 5 beds, 2 bathrooms

31 Aug – 5 Sept

4.86 out of 5 average rating, 69 reviews

Home in Chilmark

Mid-Century Gem with Private Pool & Ocean Views

4 bedrooms, 2 bathrooms

27 Aug – 1 Sept

$7,404 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

$7,193 SGD for 7 nights

5.0 out of 5 average rating, 5 reviews

Top guest favourite

Guest house in Chilmark

Beautifully Renovated 1800s Chilmark Barn

2 bedrooms, 3 beds, 1 bathroom

1–6 Sept

$2,420 SGD for 5 nights

4.95 out of 5 average rating, 99 reviews

Guest favourite

Home in West Tisbury

Beloved 5-bedroom with fenced in yard and hot tub

5 bedrooms, 8 beds, 3 bathrooms

23–28 Aug

5.0 out of 5 average rating, 10 reviews

Top guest favourite

Home in Chilmark

Peaceful Retreat Near Up-Island Beaches

2 bedrooms, 2 queen beds, 1 bathroom

20–25 Sept

$3,115 SGD for 5 nights

4.98 out of 5 average rating, 93 reviews

Guest favourite

Home in West Tisbury

Sanctuary House: An ocean-view farmhouse retreat

4 bedrooms, 5 beds, 2 bathrooms

5–10 Sept

$6,458 SGD for 5 nights

4.93 out of 5 average rating, 28 reviews

Top guest favourite

Guest house in Chilmark

Beautiful Guest House in Chilmark

1 bedroom, 1 bed, 1 bathroom

13–18 Sept

$2,488 SGD for 5 nights

4.98 out of 5 average rating, 239 reviews

Top guest favourite

Home in Chilmark

South House, Up-Island Living

3 bedrooms, 3 beds, 2 bathrooms

2–7 Sept

$6,011 SGD for 5 nights

5.0 out of 5 average rating, 6 reviews

Guest favourite

Home in Chilmark

Private Hilltop Estate with tennis court

4 bedrooms, 4 beds, 2.5 bathrooms

16–21 Aug

$51,861 SGD for 5 nights

5.0 out of 5 average rating, 12 reviews

Guest favourite

Home in West Tisbury

Tranquil & Private Waterfront Great Pond home

3 bedrooms, 4 beds, 3 bathrooms

21–28 Sept

$9,046 SGD for 7 nights

4.97 out of 5 average rating, 30 reviews

Home in Chilmark

Secluded 3 bedroom home with private beach access

4 bedrooms, 5 beds, 2 bathrooms

20–25 Sept

$5,179 SGD for 5 nights

5.0 out of 5 average rating, 16 reviews

Home in Chilmark

Tranquil Chilmark retreat

3 bedrooms, 4 beds, 2 bathrooms

23–30 Aug

$6,551 SGD for 7 nights

5.0 out of 5 average rating, 4 reviews

Superhost

Cottage in Chilmark

Menemsha Cottage

1 bedroom, 1 king bed, 1 bathroom

31 Aug – 5 Sept

$2,585 SGD for 5 nights

5.0 out of 5 average rating, 10 reviews