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Search results; Over 1,000 homes in Chilmark

Top guest favourite

Guest house in Chilmark

Beautiful Guest House in Chilmark

1 bedroom, 1 bed, 1 private bathroom

2–7 Sept

$2,665 SGD for 5 nights

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4.98 out of 5 average rating, 233 reviews

Top guest favourite

Cottage in Chilmark

Walk to the beach: Charming Menemsha Cottage

3 bedrooms, 4 beds, 3 bathrooms

5–12 Sept

$7,537 SGD for 7 nights

5.0 out of 5 average rating, 65 reviews

Top guest favourite

Guest house in West Tisbury

Vineyard Meadow Artist Studio

3 beds, 1 bathroom

20–25 Sept

$1,713 SGD for 5 nights

Free cancellation

4.97 out of 5 average rating, 113 reviews

Guest favourite

Guest suite in West Tisbury

The Abode Guest Suite. Private. Newly Renovated.

1 bed, 1 bathroom

13–18 Sept

$1,561 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 128 reviews

Home in West Tisbury

Private 5BR Vineyard Retreat - Peaceful & Central

5 bedrooms, 8 beds, 2 bathrooms

26–31 Jul

$6,129 SGD for 5 nights

Free cancellation

4.93 out of 5 average rating, 14 reviews

Guest favourite

Home in Chilmark

Path to Menemsha Beach

1 bedroom, 1 bed, 1 bathroom

6–11 Jul

$2,852 SGD for 5 nights

Free cancellation

4.88 out of 5 average rating, 8 reviews

Top guest favourite

Guest house in Chilmark

Beautifully Renovated 1800s Chilmark Barn

2 bedrooms, 3 beds, 1 bathroom

16–21 Aug

$2,513 SGD for 5 nights

4.95 out of 5 average rating, 98 reviews

Guest favourite

Home in West Tisbury

Martha’s Vineyard Farmhouse

4 bedrooms, 6 beds, 2 bathrooms

11–18 Jul

$10,621 SGD for 7 nights

Free cancellation

5.0 out of 5 average rating, 5 reviews

Top guest favourite

Home in Chilmark

Cool, Mid Century House -- Lucy Vincent Beach!

4 bedrooms, 5 beds, 3 bathrooms

17–22 Jul

$8,086 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 44 reviews

Guest favourite

Guest suite in West Tisbury

Two Bedroom Suite on Retired Horse Farm

2 bedrooms, 2 queen beds, 1 bathroom

10–15 Jul

$3,069 SGD for 5 nights

Free cancellation

4.88 out of 5 average rating, 24 reviews

Home in West Tisbury

Summer Beach Pass: Wooded Martha's Vineyard Escape

3 bedrooms, 5 beds, 2 bathrooms

11–18 Jul

$8,282 SGD for 7 nights

Free cancellation

Guest favourite

Home in Aquinnah

Peaceful Water-View Home with Large Deck & Balcony

3 bedrooms, 3 queen beds, 1.5 bathrooms

30 Aug – 4 Sept

$4,570 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 9 reviews

Top guest favourite

Home in Chilmark

2 BR-Private guest house

2 bedrooms, 2 queen beds, 1 bathroom

18–23 Jul

$4,195 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 90 reviews

Guest favourite

Guest house in West Tisbury

Bright Summer Cottage

1 bedroom, 1 queen bed, 1 bathroom

14–21 Jul

$4,264 SGD for 7 nights

Free cancellation

5.0 out of 5 average rating, 6 reviews

Guest favourite

Place to stay in Aquinnah

Water View "Tower" Room on Martha's Vineyard

1 bedroom, 1 bed, Toilet with sink

6–11 Jul

$1,500 SGD for 5 nights

Free cancellation

4.83 out of 5 average rating, 239 reviews

Guest favourite

Boutique hotel in Chilmark

Astilbe Room @ Beach Plum Inn

1 bedroom, 1 bed, 1 bathroom

6–11 Jul

$2,969 SGD for 5 nights

Free cancellation

4.86 out of 5 average rating, 7 reviews

Superhost

Cottage in Chilmark

Menemsha Inn Water View Cottage

1 bedroom, 2 beds, 1 bathroom

21–26 Jul

$3,577 SGD for 5 nights

Free cancellation

4.9 out of 5 average rating, 10 reviews

Guest favourite

Cottage in Chilmark

CHILMARK HILLTOP OCEAN VIEW

5 bedrooms, 5 beds, 2 bathrooms

6–11 Jul

$5,330 SGD for 5 nights

4.85 out of 5 average rating, 20 reviews

Top guest favourite

Home in Chilmark

Fun, Authentic, Waterfront Cottage/air conditioned

2 bedrooms, 4 beds, 1 bathroom

28 Sept – 3 Oct

$4,934 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 45 reviews