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Search results; Over 1,000 homes in Chilmark

Top guest favourite

Home in Chilmark

Cool, Mid Century House -- Lucy Vincent Beach!

4 bedrooms, 5 beds, 3 private bathrooms

24–29 Aug

$16,209 SGD for 5 nights

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4.95 out of 5 average rating, 44 reviews

Home in Chilmark

Mid-Century Gem with Private Pool & Ocean Views

4 bedrooms

30 Aug – 4 Sept

Free cancellation

4.56 out of 5 average rating, 25 reviews

Home in Chilmark

Charming North Road Retreat

4 bedrooms, 5 beds

31 Aug – 7 Sept

$7,262 SGD for 7 nights

Free cancellation

5.0 out of 5 average rating, 4 reviews

Guest favourite

Home in Chilmark

The Blueberry House on Martha’s Vineyard

2 bedrooms, 2 beds

30 Aug – 4 Sept

$4,354 SGD for 5 nights

5.0 out of 5 average rating, 26 reviews

Top guest favourite

Home in Chilmark

Renovated Barn in Chilmark 3BR

3 bedrooms, 4 beds

22–29 Aug

$6,909 SGD for 7 nights

4.99 out of 5 average rating, 106 reviews

Top guest favourite

Home in Chilmark

Fun, Authentic, Waterfront Cottage/air conditioned

2 bedrooms, 4 beds

28 Sept – 3 Oct

$4,932 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 46 reviews

Top guest favourite

Cottage in Chilmark

Walk to the beach: Charming Menemsha Cottage

3 bedrooms, 4 beds

5–12 Sept

$7,338 SGD for 7 nights

5.0 out of 5 average rating, 65 reviews

Superhost

Cottage in Chilmark

Menemsha Inn Water View Cottage

1 bedroom, 2 beds

1–6 Sept

$4,319 SGD for 5 nights

Free cancellation

4.9 out of 5 average rating, 10 reviews

Guest favourite

Home in Chilmark

Path to Menemsha Beach

1 bedroom, 1 bed

21–26 Aug

$3,654 SGD for 5 nights

Free cancellation

4.88 out of 5 average rating, 8 reviews

Home in Chilmark

Secluded 3 bedroom home with private beach access

4 bedrooms, 5 beds

20–25 Sept

$5,228 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 16 reviews

Guest favourite

Home in Chilmark

Whalehall

3 bedrooms, 4 beds

1–6 Sept

$3,805 SGD for 5 nights

Free cancellation

4.8 out of 5 average rating, 5 reviews

Top guest favourite

Guest house in Chilmark

Beautifully Renovated 1800s Chilmark Barn

2 bedrooms, 3 beds

1–6 Sept

$2,443 SGD for 5 nights

4.95 out of 5 average rating, 99 reviews

Guest favourite

Home in Chilmark

Quiet, Bright & Open MV home

4 bedrooms, 7 beds

6–11 Sept

$6,438 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 7 reviews

Guest favourite

Home in Chilmark

Chilmark Cape in private wooded setting

4 bedrooms, 5 beds

31 Aug – 5 Sept

$4,566 SGD for 5 nights

4.85 out of 5 average rating, 68 reviews

Top guest favourite

Home in Chilmark

Peaceful Retreat Near Up-Island Beaches

2 bedrooms, 2 queen beds

20–25 Sept

$3,144 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 90 reviews

Top guest favourite

Guest house in Chilmark

Beautiful Guest House in Chilmark

1 bedroom, 1 bed

2–7 Sept

$2,664 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 237 reviews

Guest favourite

Home in West Tisbury

Waterfront home with key to private Quansoo Beach

4 bedrooms, 6 beds

13–20 Sept

$7,624 SGD for 7 nights

Free cancellation

4.92 out of 5 average rating, 13 reviews

Home in Chilmark

Tranquil Chilmark retreat

3 bedrooms, 4 beds

23–30 Aug

$6,613 SGD for 7 nights

5.0 out of 5 average rating, 4 reviews

Top guest favourite

Home in West Tisbury

Vineyard Meadow Writer's Cottage with Hot Tub

3 bedrooms, 4 beds

15–20 Aug

$9,415 SGD for 5 nights

Free cancellation

4.97 out of 5 average rating, 61 reviews