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Search results; Over 1,000 homes in Chilmark

Top guest favourite

Home in Chilmark

The Blueberry House on Martha’s Vineyard

2 bedrooms, 2 beds, 2 private bathrooms

1–6 Sept

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5.0 out of 5 average rating, 28 reviews

Guest favourite

Home in Chilmark

Charming North Road Retreat

4 bedrooms, 5 beds

1–8 Sept

5.0 out of 5 average rating, 6 reviews

Guest favourite

Room in Chilmark

Astilbe Room @ Beach Plum Inn

1 bed

1–6 Sept

$2,766 SGD for 5 nights

4.86 out of 5 average rating, 7 reviews

Top guest favourite

Home in West Tisbury

Charming West Tisbury Home

5 bedrooms, 4 beds

1–6 Sept

$6,555 SGD for 5 nights

5.0 out of 5 average rating, 17 reviews

Top guest favourite

Guest house in Chilmark

Beautiful Guest House in Chilmark

1 bedroom, 1 bed

13–18 Sept

$2,469 SGD for 5 nights

4.98 out of 5 average rating, 243 reviews

Guest favourite

Room in West Tisbury

Explore Martha's Vineyard up island getaway

1 queen bed

1–6 Sept

$2,432 SGD for 5 nights

4.86 out of 5 average rating, 22 reviews

Guest favourite

Home in Chilmark

Tucked away on Tea Lane, Chilmark

4 bedrooms, 8 beds

1–8 Sept

$9,899 SGD for 7 nights

5.0 out of 5 average rating, 25 reviews

Top guest favourite

Home in Chilmark

South House, Up-Island Living

3 bedrooms, 3 beds

2–7 Sept

$5,966 SGD for 5 nights

5.0 out of 5 average rating, 7 reviews

Guest favourite

Home in West Tisbury

Light-filled Island Home

4 bedrooms, 5 beds

1–6 Sept

$5,760 SGD for 5 nights

4.95 out of 5 average rating, 20 reviews

Guest favourite

Home in Chilmark

Bayberry Cottage- Menemsha Inn & Lucy

1 bedroom, 2 beds

14–19 Sept

$2,766 SGD for 5 nights

5.0 out of 5 average rating, 5 reviews

Top guest favourite

Cottage in Chilmark

Walk to the beach: Charming Menemsha Cottage

3 bedrooms, 4 beds

14–21 Sept

5.0 out of 5 average rating, 67 reviews

Guest favourite

Home in Chilmark

Ocean view mid century modern prvt beach + LV/SQB

5 bedrooms, 7 beds

26 Sept – 3 Oct

4.95 out of 5 average rating, 19 reviews

Top guest favourite

Guest house in Chilmark

Beautifully Renovated 1800s Chilmark Barn

2 bedrooms, 3 beds

1–6 Sept

$2,402 SGD for 5 nights

4.95 out of 5 average rating, 101 reviews

Guest favourite

Home in West Tisbury

Spacious, Private Cape in W. Tisbury

4 bedrooms, 6 beds

14–21 Sept

$8,395 SGD for 7 nights

5.0 out of 5 average rating, 6 reviews

Guest favourite

Home in Aquinnah

Amazing Views!!Sunsets!!HistoricMV Gem&Lg.RoofDeck

3 bedrooms, 5 beds

16–21 Oct

$2,442 SGD for 5 nights

4.89 out of 5 average rating, 54 reviews

Guest favourite

Home in Chilmark

Tranquil Chilmark retreat

3 bedrooms, 4 beds

6–13 Sept

$6,992 SGD for 7 nights

5.0 out of 5 average rating, 5 reviews

Top guest favourite

Guest suite in West Tisbury

The Loft Guest Suite. Private. Newly Renovated.

1 queen bed

27 Sept – 2 Oct

4.95 out of 5 average rating, 184 reviews

Superhost

Home in Chilmark

Evelyn's Menemsha Camp - Best Vineyard View

3 bedrooms, 4 beds

20–25 Sept

$4,517 SGD for 5 nights

4.85 out of 5 average rating, 20 reviews

Guest favourite

Home in West Tisbury

Secluded and Serene Getaway

5 bedrooms, 12 beds

19–24 Sept

$5,050 SGD for 5 nights

5.0 out of 5 average rating, 9 reviews