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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

$2,058 SGD for 5 nights

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4.99 out of 5 average rating, 114 reviews

Top guest favourite

Home in Chilmark

Fun, Authentic, Waterfront Cottage/air conditioned

2 bedrooms, 4 beds, 1 bathroom

28 Sept – 3 Oct

$4,890 SGD for 5 nights

4.98 out of 5 average rating, 48 reviews

Top guest favourite

Guest house in Chilmark

Beautifully Renovated 1800s Chilmark Barn

2 bedrooms, 3 beds, 1 bathroom

1–6 Sept

$2,423 SGD for 5 nights

4.95 out of 5 average rating, 100 reviews

Top guest favourite

Home in Chilmark

The Blueberry House on Martha’s Vineyard

2 bedrooms, 2 beds, 2 bathrooms

30 Aug – 4 Sept

$4,318 SGD for 5 nights

5.0 out of 5 average rating, 27 reviews

Guest favourite

Home in Chilmark

Chilmark Cape in private wooded setting

4 bedrooms, 5 beds, 2 bathrooms

31 Aug – 5 Sept

4.84 out of 5 average rating, 70 reviews

Top guest favourite

Guest house in Chilmark

Beautiful Guest House in Chilmark

1 bedroom, 1 bed, 1 bathroom

13–18 Sept

$2,491 SGD for 5 nights

4.98 out of 5 average rating, 240 reviews

Superhost

Home in Chilmark

Evelyn's Menemsha Camp - Best Vineyard View

3 bedrooms, 4 beds, 2 bathrooms

20–25 Sept

$5,344 SGD for 5 nights

4.85 out of 5 average rating, 20 reviews

Home in Chilmark

Mid-Century Gem with Private Pool & Ocean Views

4 bedrooms, 2 bathrooms

27 Aug – 1 Sept

$7,010 SGD for 5 nights

4.58 out of 5 average rating, 26 reviews

Top guest favourite

Home in Chilmark

Renovated Barn in Chilmark 3BR

3 bedrooms, 4 beds, 2 bathrooms

22–29 Aug

$6,852 SGD for 7 nights

4.99 out of 5 average rating, 108 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

Superhost

Cottage in Chilmark

Charming 1 BR Ocean View Cottage, Path to Beach

1 bedroom, 2 beds, 1 bathroom

30 Aug – 4 Sept

$2,942 SGD for 5 nights

4.94 out of 5 average rating, 17 reviews

Guest favourite

Home in Chilmark

Charming North Road Retreat

4 bedrooms, 5 beds, 4 bathrooms

31 Aug – 7 Sept

$7,201 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

$3,118 SGD for 5 nights

4.98 out of 5 average rating, 93 reviews

Guest favourite

Guest suite in West Tisbury

The Apartment Guest Suite. Private. Just Renovated

1 queen bed, 1 bathroom

7–12 Sept

$1,623 SGD for 5 nights

4.95 out of 5 average rating, 134 reviews

Guest favourite

Place to stay in Aquinnah

Water View "Tower" Room on Martha's Vineyard

1 bedroom, 1 bed, WC

20–25 Sept

$1,298 SGD for 5 nights

4.83 out of 5 average rating, 242 reviews

Top guest favourite

Guest house in West Tisbury

Vineyard Meadow Artist Studio

3 beds, 1 bathroom

20–25 Sept

$1,655 SGD for 5 nights

4.98 out of 5 average rating, 122 reviews

Guest favourite

Home in West Tisbury

Vineyard Meadow Writer's Cottage with Hot Tub

3 bedrooms, 4 beds, 2 bathrooms

7–12 Sept

$4,555 SGD for 5 nights

4.97 out of 5 average rating, 61 reviews

Guest favourite

Room in Chilmark

Astilbe Room @ Beach Plum Inn

1 bed, 1 bathroom

30 Aug – 4 Sept

$2,942 SGD for 5 nights

4.86 out of 5 average rating, 7 reviews

Superhost

Cottage in Chilmark

Chilmark, Martha' s Vineyard Water View Cottage

1 bedroom, 1 king bed, 1 bathroom

31 Aug – 5 Sept

$2,587 SGD for 5 nights

4.83 out of 5 average rating, 12 reviews