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Search results; Over 1,000 homes in Chilmark

Top guest favourite

Guest house in Chlmark

4-Season Guest House on Historic Chilmark Estate

1 bedroom, 1 bed, 1 private bathroom

20–25 Sept

$2,137 SGD for 5 nights

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4.99 out of 5 average rating, 110 reviews

Top guest favourite

Guest house in Chilmark

Beautiful Guest House in Chilmark

1 bedroom, 1 bed, 1 bathroom

2–7 Sept

$2,671 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 233 reviews

Home in Chilmark

Tranquil Chilmark retreat

3 bedrooms, 4 beds, 2 bathrooms

5–12 Jul

$7,324 SGD for 7 nights

5.0 out of 5 average rating, 4 reviews

Top guest favourite

Cottage in Chilmark

Walk to the beach: Charming Menemsha Cottage

3 bedrooms, 4 beds, 3 bathrooms

5–12 Sept

$7,553 SGD for 7 nights

5.0 out of 5 average rating, 62 reviews

Guest favourite

Cottage in Chilmark

CHILMARK HILLTOP OCEAN VIEW

5 bedrooms, 5 beds, 2 bathrooms

1–6 Jul

$5,681 SGD for 5 nights

4.84 out of 5 average rating, 19 reviews

Top guest favourite

Guest house in West Tisbury

Vineyard Meadow Artist Studio

3 beds, 1 bathroom

20–25 Sept

$1,717 SGD for 5 nights

Free cancellation

4.97 out of 5 average rating, 112 reviews

Guest favourite

Home in West Tisbury

Light-filled Island Home

4 bedrooms, 5 beds, 3.5 bathrooms

1–6 Jul

4.94 out of 5 average rating, 18 reviews

Guest favourite

Home in Chilmark

Secluded 3 bedroom home with private beach access

4 bedrooms, 5 beds, 2 bathrooms

20–25 Sept

$5,241 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 16 reviews

Guest favourite

Home in Chilmark

Path to Menemsha Beach

1 bedroom, 1 bed, 1 bathroom

1–6 Jul

$3,149 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

1–6 Sept

$2,518 SGD for 5 nights

4.95 out of 5 average rating, 99 reviews

Superhost

Hotel in Chilmark

Wreath Bungalow @ Beach Plum Inn

1 bedroom, 1 bed, 1 bathroom

3–8 Jul

$3,464 SGD for 5 nights

Free cancellation

Guest favourite

Guest suite in West Tisbury

The Abode Guest Suite. Private. Newly Renovated.

1 bed, 1 bathroom

13–18 Sept

$1,564 SGD for 5 nights

Free cancellation

4.94 out of 5 average rating, 127 reviews

Top guest favourite

Home in Chilmark

Cool, Mid Century House -- Lucy Vincent Beach!

4 bedrooms, 5 beds, 3 bathrooms

6–11 Jul

Free cancellation

4.95 out of 5 average rating, 43 reviews

Home in Chilmark

Whalehall

3 bedrooms, 4 beds, 2 bathrooms

1–6 Sept

$3,815 SGD for 5 nights

Pay $0 today

Free cancellation

4.75 out of 5 average rating, 4 reviews

Guest favourite

Guest suite in West Tisbury

Two Bedroom Suite on Retired Horse Farm

2 bedrooms, 2 queen beds, 1 bathroom

3–8 Sept

$3,075 SGD for 5 nights

Free cancellation

4.88 out of 5 average rating, 24 reviews

Guest favourite

Guest suite in West Tisbury

Quiet West Tisbury 2 BDR Suite

2 bedrooms, 2 queen beds, 1 bathroom

18–23 Jul

$2,716 SGD for 5 nights

Free cancellation

4.97 out of 5 average rating, 88 reviews

Top guest favourite

Home in Chilmark

2 BR-Private guest house

2 bedrooms, 2 queen beds, 1 bathroom

18–23 Jul

$4,242 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 89 reviews

Home in Aquinnah

Kane Farmhouse

4 bedrooms, 5 beds, 2 bathrooms

1–8 Nov

$9,002 SGD for 7 nights

Free cancellation

Superhost

Flat in Aquinnah

Quiet & Serene in Aquinnah

2 bedrooms, 2 beds, 1 bathroom

1–8 Jul

Free cancellation

4.74 out of 5 average rating, 31 reviews