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Search results; Over 1,000 homes in Chilmark

Descriptions are based on details hosts provide

Top guest favourite

Home in Chilmark

2 BR-Private guest house

2 bedrooms, 2 beds, 1 shared bathroom

18–23 Jul

$4,082 SGD for 5 nights

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4.98 out of 5 average rating, 90 reviews

Top guest favourite

Cottage in Chilmark

Renovated 1950s cottage, walk to Menemsha

3 bedrooms, 4 beds, 3 bathrooms

5–12 Sept

$7,337 SGD for 7 nights

5.0 out of 5 average rating, 65 reviews

Top guest favourite

Home in West Tisbury

Cozy 3BR Cottage with Lambert's Cove Beach access

3 bedrooms, 5 beds, 2.5 bathrooms

6–11 Sept

$3,846 SGD for 5 nights

5.0 out of 5 average rating, 7 reviews

Top guest favourite

Home in Chilmark

Fun, Authentic, Waterfront Cottage/air conditioned

2 bedrooms, 4 beds, 1 bathroom

28 Sept – 3 Oct

$4,950 SGD for 5 nights

4.98 out of 5 average rating, 46 reviews

Top guest favourite

Home in Chilmark

Cool, Mid Century House -- Lucy Vincent Beach!

4 bedrooms, 5 beds, 3 bathrooms

23–28 Jul

$7,928 SGD for 5 nights

4.95 out of 5 average rating, 44 reviews

Home in Chilmark

1964 Eliot Noyes home with ocean views

4 bedrooms, 2 bathrooms

30 Aug – 4 Sept

4.56 out of 5 average rating, 25 reviews

Top guest favourite

Guest house in Chilmark

Beach pass to Lucy Vincent included

1 bedroom, 1 bed, 1 bathroom

2–7 Sept

$2,663 SGD for 5 nights

4.98 out of 5 average rating, 235 reviews

Guest favourite

Home in Chilmark

Designer cottage near Menemsha Beach

2 bedrooms, 2 beds, 2 bathrooms

30 Aug – 4 Sept

$4,559 SGD for 5 nights

5.0 out of 5 average rating, 25 reviews

Top guest favourite

Guest house in Chilmark

Renovated 1800s barn with original beams

2 bedrooms, 3 beds, 1 bathroom

16–21 Aug

$2,443 SGD for 5 nights

4.95 out of 5 average rating, 98 reviews

Top guest favourite

Home in Chilmark

Renovated Barn in Chilmark 3BR

3 bedrooms, 4 beds, 2 bathrooms

22–29 Aug

$7,094 SGD for 7 nights

4.99 out of 5 average rating, 106 reviews

Guest favourite

Home in West Tisbury

Wooded retreat with pond, dock, and kayak

3 bedrooms, 5 beds, 2 bathrooms

12–19 Sept

$4,375 SGD for 7 nights

4.91 out of 5 average rating, 45 reviews

Home in Chilmark

Private beach on Menemsha Pond

4 bedrooms, 5 beds, 2 bathrooms

20–25 Sept

5.0 out of 5 average rating, 16 reviews

Guest favourite

Home in Chilmark

Chilmark Cape in private wooded setting

4 bedrooms, 5 beds, 2 bathrooms

31 Aug – 5 Sept

$4,565 SGD for 5 nights

4.85 out of 5 average rating, 68 reviews

Home in Chilmark

Charming North Road Retreat

4 bedrooms, 5 beds, 4 bathrooms

31 Aug – 7 Sept

$7,260 SGD for 7 nights

5.0 out of 5 average rating, 4 reviews

Top guest favourite

Home in West Tisbury

Up-Island Escape, Long Point Beach

4 bedrooms, 6 beds, 3 bathrooms

28 Sept – 4 Oct

$4,207 SGD for 6 nights

4.98 out of 5 average rating, 222 reviews

Guest favourite

Place to stay in Aquinnah

Water View "Tower" Room on Martha's Vineyard

1 bedroom, 1 bed, WC

20–25 Sept

$1,309 SGD for 5 nights

4.83 out of 5 average rating, 239 reviews

Guest favourite

Home in Aquinnah

MARTHA'S VINEYARD AQUINNAH OCEAN VIEW CLAY PIT RD

4 bedrooms, 7 beds, 4 bathrooms

18–24 Jul

$8,892 SGD for 6 nights

4.84 out of 5 average rating, 25 reviews

Guest favourite

Home in West Tisbury

Includes a car and beach pass

3 bedrooms, 6 beds, 2 bathrooms

22–27 Aug

$6,602 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 9 reviews

Top guest favourite

Home in West Tisbury

Vineyard Meadow Writer's Cottage with Hot Tub

3 bedrooms, 4 beds, 2 bathrooms

15–20 Aug

$9,414 SGD for 5 nights

4.97 out of 5 average rating, 61 reviews