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Search results; Over 1,000 homes in Chilmark

Top guest favourite

Home in Chilmark

2 BR-Private guest house

2 bedrooms, 2 beds, 1 shared bathroom

18–23 Jul

$4,237 SGD for 5 nights

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4.98 out of 5 average rating, 90 reviews

Top guest favourite

Cottage in Chilmark

Walk to the beach: Charming Menemsha Cottage

3 bedrooms, 4 beds, 3 bathrooms

5–12 Sept

$7,543 SGD for 7 nights

5.0 out of 5 average rating, 63 reviews

Home in Chilmark

Charming North Road Retreat

4 bedrooms, 5 beds, 4 bathrooms

9–16 Jul

$7,543 SGD for 7 nights

Free cancellation

5.0 out of 5 average rating, 3 reviews

Top guest favourite

Home in Chilmark

Fun, Authentic, Waterfront Cottage/air conditioned

2 bedrooms, 4 beds, 1 bathroom

28 Sept – 3 Oct

$4,937 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 44 reviews

Guest favourite

Home in Chilmark

The Blueberry House on Martha’s Vineyard

2 bedrooms, 2 beds, 2 bathrooms

30 Aug – 4 Sept

$5,021 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 24 reviews

Top guest favourite

Guest house in Chilmark

Beautifully Renovated 1800s Chilmark Barn

2 bedrooms, 3 beds, 1 bathroom

16–21 Aug

$2,515 SGD for 5 nights

4.95 out of 5 average rating, 98 reviews

Top guest favourite

Guest house in Chilmark

Beautiful Guest House in Chilmark

1 bedroom, 1 bed, 1 bathroom

2–7 Sept

$2,667 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 233 reviews

Guest favourite

Home in Chilmark

Secluded 3 bedroom home with private beach access

4 bedrooms, 5 beds, 2 bathrooms

20–25 Sept

Free cancellation

5.0 out of 5 average rating, 16 reviews

Top guest favourite

Home in Chilmark

Renovated Barn in Chilmark 3BR

3 bedrooms, 4 beds, 2 bathrooms

22–29 Aug

$7,104 SGD for 7 nights

4.99 out of 5 average rating, 106 reviews

Top guest favourite

Home in Chilmark

Cool, Mid Century House -- Lucy Vincent Beach!

4 bedrooms, 5 beds, 3 bathrooms

6–11 Jul

$14,065 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 43 reviews

Guest favourite

Home in Chilmark

Historic Brick Barn in Chilmark

2 bedrooms, 3 beds, 1 bathroom

25–30 Jul

$6,362 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 55 reviews

Guest favourite

Home in Chilmark

The Charming Cove House

3 bedrooms, 4 beds, 1.5 bathrooms

11–18 Jul

$7,452 SGD for 7 nights

4.95 out of 5 average rating, 19 reviews

Guest favourite

Home in Chilmark

Chilmark Cape in private wooded setting

4 bedrooms, 5 beds, 2 bathrooms

5–10 Jul

$7,124 SGD for 5 nights

Free cancellation

4.85 out of 5 average rating, 68 reviews

Top guest favourite

Home in West Tisbury

Vineyard Meadow Writer's Cottage with Hot Tub

3 bedrooms, 4 beds, 2 bathrooms

13–18 Jul

Free cancellation

4.97 out of 5 average rating, 59 reviews

Guest favourite

Home in Chilmark

Private Hilltop Estate with tennis court

4 bedrooms, 4 beds, 2.5 bathrooms

17–22 Jul

$23,656 SGD for 5 nights

5.0 out of 5 average rating, 10 reviews

Home in Chilmark

Tranquil Chilmark retreat

3 bedrooms, 4 beds, 2 bathrooms

5–12 Jul

$7,315 SGD for 7 nights

5.0 out of 5 average rating, 4 reviews

Guest favourite

Home in Aquinnah

Modern Aquinnah home close to the beach- 5 beds

4 bedrooms, 5 beds, 2 bathrooms

26 Sept – 1 Oct

$4,889 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 20 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

$4,229 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 7 reviews

Guest favourite

Cottage in Chilmark

CHILMARK HILLTOP OCEAN VIEW

5 bedrooms, 5 beds, 2 bathrooms

1–6 Jul

$5,684 SGD for 5 nights

4.84 out of 5 average rating, 19 reviews