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Search results; Over 1,000 homes in Chilmark

Superhost

Home in Chilmark

Comfortable 3BR Home, minutes from Menemsha Harbor

3 bedrooms, 4 beds, 2 private bathrooms

26–31 Aug

$5,863 SGD for 5 nights

,

4.79 out of 5 average rating, 19 reviews

Top guest favourite

Home in Chilmark

Fun, Authentic, Waterfront Cottage/air conditioned

2 bedrooms, 4 beds, 1 bathroom

28 Sept – 3 Oct

$4,892 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

$2,424 SGD for 5 nights

4.95 out of 5 average rating, 99 reviews

Top guest favourite

Home in Chilmark

The Blueberry House on Martha’s Vineyard

2 bedrooms, 2 beds, 2 bathrooms

30 Aug – 4 Sept

$4,319 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

4.86 out of 5 average rating, 69 reviews

Top guest favourite

Guest house in Chilmark

Beautiful Guest House in Chilmark

1 bedroom, 1 bed, 1 bathroom

13–18 Sept

$2,492 SGD for 5 nights

4.98 out of 5 average rating, 239 reviews

Superhost

Hotel in Chilmark

Sage Room @The Beach Plum Inn

1 bedroom, 1 bed, 1 bathroom

13–18 Sept

4.75 out of 5 average rating, 4 reviews

Superhost

Home in Chilmark

Evelyn's Menemsha Camp - Best Vineyard View

3 bedrooms, 4 beds, 2 bathrooms

20–25 Sept

$5,346 SGD for 5 nights

4.85 out of 5 average rating, 20 reviews

Top guest favourite

Home in Chilmark

Renovated Barn in Chilmark 3BR

3 bedrooms, 4 beds, 2 bathrooms

22–29 Aug

$6,854 SGD for 7 nights

4.99 out of 5 average rating, 106 reviews

Home in Chilmark

Mid-Century Gem with Private Pool & Ocean Views

4 bedrooms, 2 bathrooms

27 Aug – 1 Sept

$7,448 SGD for 5 nights

4.56 out of 5 average rating, 25 reviews

Superhost

Cottage in Chilmark

Charming 1 BR Ocean View Cottage, Path to Beach

1 bedroom, 2 beds, 1 bathroom

30 Aug – 4 Sept

$2,872 SGD for 5 nights

4.94 out of 5 average rating, 17 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

Guest favourite

Place to stay in Aquinnah

Water View "Tower" Room on Martha's Vineyard

1 bedroom, 1 bed, WC

20–25 Sept

$1,299 SGD for 5 nights

4.83 out of 5 average rating, 241 reviews

Guest favourite

Home in Chilmark

Charming North Road Retreat

4 bedrooms, 5 beds, 4 bathrooms

31 Aug – 7 Sept

$7,204 SGD for 7 nights

5.0 out of 5 average rating, 5 reviews

Guest favourite

Home in West Tisbury

Vineyard Meadow Writer's Cottage with Hot Tub

3 bedrooms, 4 beds, 2 bathrooms

7–12 Sept

$4,556 SGD for 5 nights

4.97 out of 5 average rating, 61 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, 121 reviews

Top guest favourite

Home in Chilmark

Peaceful Retreat Near Up-Island Beaches

2 bedrooms, 2 queen beds, 1 bathroom

20–25 Sept

$3,119 SGD for 5 nights

4.98 out of 5 average rating, 92 reviews

Top guest favourite

Guest suite in West Tisbury

The Loft Guest Suite. Private. Newly Renovated.

1 queen bed, 1 bathroom

14–19 Sept

$1,586 SGD for 5 nights

4.94 out of 5 average rating, 180 reviews

Guest favourite

Home in Chilmark

Private Hilltop Estate with tennis court

4 bedrooms, 4 beds, 2.5 bathrooms

16–21 Aug

$45,533 SGD for 5 nights

5.0 out of 5 average rating, 12 reviews