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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

$4,232 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

$7,535 SGD for 7 nights

5.0 out of 5 average rating, 64 reviews

Guest favourite

Home in Chilmark

Secluded 3 bedroom home with private beach access

4 bedrooms, 5 beds, 2 bathrooms

20–25 Sept

5.0 out of 5 average rating, 16 reviews

Top guest favourite

Home in Chilmark

Fun, Authentic, Waterfront Cottage/air conditioned

2 bedrooms, 4 beds, 1 bathroom

28 Sept – 3 Oct

$4,932 SGD for 5 nights

4.98 out of 5 average rating, 45 reviews

Top guest favourite

Home in Chilmark

Cool, Mid Century House -- Lucy Vincent Beach!

4 bedrooms, 5 beds, 3 bathrooms

17–22 Jul

$8,236 SGD for 5 nights

4.95 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

$5,016 SGD for 5 nights

5.0 out of 5 average rating, 25 reviews

Guest favourite

Home in Chilmark

Chilmark Cape in private wooded setting

4 bedrooms, 5 beds, 2 bathrooms

5–10 Jul

$7,117 SGD for 5 nights

4.85 out of 5 average rating, 68 reviews

Top guest favourite

Guest house in Chilmark

Beautifully Renovated 1800s Chilmark Barn

2 bedrooms, 3 beds, 1 bathroom

16–21 Aug

$2,512 SGD for 5 nights

4.95 out of 5 average rating, 98 reviews

Home in Chilmark

Charming North Road Retreat

4 bedrooms, 5 beds, 4 bathrooms

9–16 Jul

$7,535 SGD for 7 nights

5.0 out of 5 average rating, 3 reviews

Top guest favourite

Guest house in Chilmark

Beautiful Guest House in Chilmark

1 bedroom, 1 bed, 1 bathroom

2–7 Sept

$2,664 SGD for 5 nights

4.98 out of 5 average rating, 233 reviews

Top guest favourite

Home in Chilmark

Renovated Barn in Chilmark 3BR

3 bedrooms, 4 beds, 2 bathrooms

22–29 Aug

$7,097 SGD for 7 nights

4.99 out of 5 average rating, 106 reviews

Guest favourite

Home in West Tisbury

3BR Home, Fenced Yard, Free use of car, Pets ok!

3 bedrooms, 6 beds, 2 bathrooms

22–27 Aug

$6,664 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 9 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

$4,225 SGD for 5 nights

5.0 out of 5 average rating, 7 reviews

Guest favourite

Home in West Tisbury

Martha’s Vineyard Farmhouse

4 bedrooms, 6 beds, 2 bathrooms

11–18 Jul

$10,713 SGD for 7 nights

5.0 out of 5 average rating, 5 reviews

Guest favourite

Home in West Tisbury

Tranquil & Private Waterfront Great Pond home

3 bedrooms, 4 beds, 3 bathrooms

5–10 Jul

$6,281 SGD for 5 nights

4.96 out of 5 average rating, 28 reviews

Top guest favourite

Home in West Tisbury

Up-Island Escape, Long Point Beach

4 bedrooms, 6 beds, 3 bathrooms

28 Sept – 4 Oct

$4,324 SGD for 6 nights

4.98 out of 5 average rating, 222 reviews

Superhost

Home in Oak Bluffs

NEW! Charming Oak Bluffs Cottage - Sleeps 8

3 bedrooms, 4 beds, 2 bathrooms

7–12 Jul

New home discount

New place to stay

Superhost

Cottage in Chilmark

Spacious 2 BR Cottage, Ocean View, Path to Beach

2 bedrooms, 4 beds, 1 bathroom

5–10 Jul

$3,733 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Home in Chilmark

Cozy house on private beach

1 bedroom, 2 beds, 1 bathroom

25 Aug – 1 Sept

$5,328 SGD for 7 nights