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Search results; Over 1,000 homes in Chilmark

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Top guest favourite

Home in Chilmark

The Blueberry House on Martha’s Vineyard

2 bedrooms, 2 beds, 2 private bathrooms

21–26 Sept

$3,031 SGD for 5 nights

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5.0 out of 5 average rating, 29 reviews

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Top guest favourite

Cottage in Chilmark

Walk to the beach: Charming Menemsha Cottage

3 bedrooms, 4 beds, 3 bathrooms

17–22 Sept

5.0 out of 5 average rating, 69 reviews

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Superhost

Home in Chilmark

Chilmark Cape in private wooded setting

4 bedrooms, 5 beds, 2 bathrooms

4–9 Oct

$3,247 SGD for 5 nights

4.85 out of 5 average rating, 74 reviews

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Top guest favourite

Home in Chilmark

Fun, Authentic, Waterfront Cottage/air conditioned

2 bedrooms, 4 beds, 1 bathroom

5–10 Oct

$4,126 SGD for 5 nights

4.98 out of 5 average rating, 51 reviews

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Superhost

Home in Chilmark

Evelyn's Menemsha Camp - Best Vineyard View

3 bedrooms, 4 beds, 2 bathrooms

20–25 Sept

$4,841 SGD for 5 nights

4.85 out of 5 average rating, 20 reviews

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Top guest favourite

Home in Chilmark

Renovated Barn in Chilmark 3BR

3 bedrooms, 4 beds, 2 bathrooms

5–10 Oct

4.99 out of 5 average rating, 110 reviews

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Top guest favourite

Guest house in Chilmark

Beautifully Renovated 1800s Chilmark Barn

2 bedrooms, 3 beds, 1 bathroom

24–29 Sept

$1,862 SGD for 5 nights

4.95 out of 5 average rating, 103 reviews

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Home in West Tisbury

NEW BUILD: A Love Letter to MV

4 bedrooms, 5 beds, 3.5 bathrooms

25–30 Sept

5.0 out of 5 average rating, 3 reviews

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Top guest favourite

Home in Chilmark

South House, Up-Island Living

3 bedrooms, 3 beds, 2 bathrooms

17–24 Sept

$8,983 SGD for 7 nights

5.0 out of 5 average rating, 8 reviews

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Guest favourite

Home in Chilmark

Charming North Road Retreat

4 bedrooms, 5 beds, 4 bathrooms

18–23 Sept

5.0 out of 5 average rating, 7 reviews

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Guest favourite

Home in Chilmark

Quiet, Bright & Open MV home

4 bedrooms, 7 beds, 2 bathrooms

23–28 Aug

$5,450 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 11 reviews

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Top guest favourite

Guest house in Chilmark

Beautiful Guest House in Chilmark

1 bedroom, 1 bed, 1 bathroom

17–22 Sept

$2,557 SGD for 5 nights

4.98 out of 5 average rating, 247 reviews

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Home in Chilmark

Classic Chilmark Charm

7 bedrooms, 8 beds, 3.5 bathrooms

21–26 Sept

$4,165 SGD for 5 nights

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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

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Guest favourite

Home in West Tisbury

Tranquil & Private Waterfront Great Pond home

3 bedrooms, 4 beds, 3 bathrooms

12–19 Jun

Book early to save

4.97 out of 5 average rating, 32 reviews

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Top guest favourite

Home in West Tisbury

Up-Island Escape, Long Point Beach

4 bedrooms, 6 beds, 3 bathrooms

28 Sept – 4 Oct

4.98 out of 5 average rating, 230 reviews

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Cottage in Chilmark

Charming Chilmark cottage with Atlantic view

2 bedrooms, 3 beds, 2 bathrooms

28 Sept – 3 Oct

$4,202 SGD for 5 nights

Free cancellation

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Guest favourite

Home in West Tisbury

Secluded and Serene Getaway

5 bedrooms, 12 beds, 2 bathrooms

19–24 Sept

$4,712 SGD for 5 nights

5.0 out of 5 average rating, 10 reviews

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Top guest favourite

Home in West Tisbury

Vineyard Meadow Writer's Cottage with Hot Tub

3 bedrooms, 4 beds, 2 bathrooms

17–22 Sept

4.97 out of 5 average rating, 64 reviews