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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

,

4.98 out of 5 average rating, 236 reviews

Top guest favourite

Home in Chilmark

Fun, Authentic, Waterfront Cottage/air conditioned

2 bedrooms, 4 beds, 1 bathroom

28 Sept – 3 Oct

$4,933 SGD for 5 nights

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, 3 bathrooms

5–12 Sept

$7,340 SGD for 7 nights

5.0 out of 5 average rating, 65 reviews

Top guest favourite

Guest house in Chilmark

Beautifully Renovated 1800s Chilmark Barn

2 bedrooms, 3 beds, 1 bathroom

1–6 Sept

$2,444 SGD for 5 nights

4.95 out of 5 average rating, 99 reviews

Top guest favourite

Home in Chilmark

Cool, Mid Century House -- Lucy Vincent Beach!

4 bedrooms, 5 beds, 3 bathrooms

23–28 Jul

4.95 out of 5 average rating, 44 reviews

Home in Chilmark

Mid-Century Gem with Private Pool & Ocean Views

4 bedrooms, 2 bathrooms

30 Aug – 4 Sept

4.56 out of 5 average rating, 25 reviews

Guest favourite

Home in Chilmark

The Blueberry House on Martha’s Vineyard

2 bedrooms, 2 beds, 2 bathrooms

30 Aug – 4 Sept

$4,355 SGD for 5 nights

5.0 out of 5 average rating, 26 reviews

Top guest favourite

Home in Chilmark

Peaceful Retreat Near Up-Island Beaches

2 bedrooms, 2 queen beds, 1 bathroom

20–25 Sept

$3,107 SGD for 5 nights

4.98 out of 5 average rating, 90 reviews

Top guest favourite

Home in Chilmark

Renovated Barn in Chilmark 3BR

3 bedrooms, 4 beds, 2 bathrooms

22–29 Aug

$6,911 SGD for 7 nights

4.99 out of 5 average rating, 106 reviews

Home in Chilmark

Charming North Road Retreat

4 bedrooms, 5 beds, 4 bathrooms

31 Aug – 7 Sept

$7,264 SGD for 7 nights

5.0 out of 5 average rating, 4 reviews

Guest favourite

Home in Chilmark

Chilmark Cape in private wooded setting

4 bedrooms, 5 beds, 2 bathrooms

31 Aug – 5 Sept

$4,568 SGD for 5 nights

4.85 out of 5 average rating, 68 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

$3,848 SGD for 5 nights

5.0 out of 5 average rating, 7 reviews

Guest favourite

Home in Aquinnah

MARTHA'S VINEYARD AQUINNAH OCEAN VIEW CLAY PIT RD

4 bedrooms, 7 beds, 4 bathrooms

31 Jul – 6 Aug

$8,896 SGD for 6 nights

4.84 out of 5 average rating, 25 reviews

Top guest favourite

Home in West Tisbury

Vineyard Meadow Writer's Cottage with Hot Tub

3 bedrooms, 4 beds, 2 bathrooms

15–20 Aug

$9,418 SGD for 5 nights

4.97 out of 5 average rating, 61 reviews

Guest favourite

Home in Chilmark

Path to Menemsha Beach

1 bedroom, 1 bed, 1 bathroom

25–30 Jul

$3,495 SGD for 5 nights

4.88 out of 5 average rating, 8 reviews

Guest favourite

Home in Chilmark

Quiet, Bright & Open MV home

4 bedrooms, 7 beds, 2 bathrooms

6–11 Sept

$6,440 SGD for 5 nights

5.0 out of 5 average rating, 7 reviews

Top guest favourite

Home in Chilmark

South House, Up-Island Living

3 bedrooms, 3 beds, 2 bathrooms

2–7 Sept

$6,071 SGD for 5 nights

5.0 out of 5 average rating, 6 reviews

Guest favourite

Home in Chilmark

Private Hilltop Estate with tennis court

4 bedrooms, 4 beds, 2.5 bathrooms

21–26 Jul

$52,662 SGD for 5 nights

5.0 out of 5 average rating, 10 reviews

Guest favourite

Home in Chilmark

Whalehall

3 bedrooms, 4 beds, 2 bathrooms

1–6 Sept

$3,806 SGD for 5 nights

4.8 out of 5 average rating, 5 reviews