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Search results; Over 1,000 homes in Oak Bluffs

Top guest favourite

Home in Oak Bluffs

The Luxury Vineyard Yurt

2 bedrooms, 3 beds, 1 private bathroom

19–24 Oct

$2,558 SGD for 5 nights

,

4.93 out of 5 average rating, 316 reviews

Home in Oak Bluffs

Amanda’s Veranda

4 bedrooms, 5 beds

27 Sept – 2 Oct

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Free cancellation

New place to stay

Top guest favourite

Cottage in Oak Bluffs

111I Beautiful and walk to everything Oak Bluffs!

1 bedroom, 2 beds

13–18 Sept

4.97 out of 5 average rating, 184 reviews

Superhost

Cottage in Oak Bluffs

#Islandbeachrose. Walk To Beach and Town!

4 bedrooms, 6 beds

6–13 Sept

$8,787 SGD for 7 nights

4.92 out of 5 average rating, 26 reviews

Guest favourite

Home in Oak Bluffs

Oak Bluffs Victorian Walk to Town & Beaches

5 bedrooms, 7 beds

29 Sept – 4 Oct

$10,552 SGD for 5 nights

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Free cancellation

4.82 out of 5 average rating, 67 reviews

Home in Oak Bluffs

East Chop Oceanview Escape

6 bedrooms, 8 beds

21–27 Aug

$29,694 SGD for 6 nights

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Free cancellation

5.0 out of 5 average rating, 4 reviews

Home in Oak Bluffs

Oak Bluffs Summer Home

3 bedrooms, 4 beds

30 Aug – 4 Sept

$6,352 SGD for 5 nights

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Free cancellation

4.67 out of 5 average rating, 3 reviews

Guest favourite

Guest suite in Oak Bluffs

Lovely 2 BR Oak Bluffs Apartment

2 bedrooms, 2 double beds

18–23 Oct

$1,236 SGD for 5 nights

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4.95 out of 5 average rating, 428 reviews

Guest favourite

Home in Oak Bluffs

Modern cabin in the woods.

3 bedrooms, 4 beds

1–6 Sept

$4,259 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 7 reviews

Top guest favourite

Home in Oak Bluffs

The Blue Lagoon, Oak Bluffs

3 bedrooms, 3 king beds

27 Sept – 2 Oct

$4,881 SGD for 5 nights

4.98 out of 5 average rating, 54 reviews

Guest favourite

Home in Oak Bluffs

New Pristine Luxury Home on Martha's Vineyard

3 bedrooms, 6 beds

31 Aug – 5 Sept

$5,581 SGD for 5 nights

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Free cancellation

4.98 out of 5 average rating, 86 reviews

Top guest favourite

Cottage in Oak Bluffs

The WestLake

4 bedrooms, 5 beds

3–8 Oct

$4,758 SGD for 5 nights

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5.0 out of 5 average rating, 12 reviews

Guest favourite

Home in Oak Bluffs

New Serenity Retreat

2 bedrooms, 3 beds

29 Aug – 3 Sept

$5,024 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 7 reviews

Top guest favourite

Home in Oak Bluffs

Spectacular beach & pool combo; beautiful sunsets!

4 bedrooms, 5 beds

4–9 Oct

$4,334 SGD for 5 nights

4.93 out of 5 average rating, 221 reviews

Top guest favourite

Home in Oak Bluffs

**Vineyard Vacation Retreat** -3 BR

3 bedrooms, 3 beds

8–13 Sept

$6,441 SGD for 5 nights

4.96 out of 5 average rating, 131 reviews

Top guest favourite

Home in Tisbury

Martha’s Vineyard Waterfront Private Beach

8 bedrooms, 10 beds

20–25 Sept

$16,823 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 18 reviews

Guest favourite

Home in Oak Bluffs

Oak Bluffs Harbor View

4 bedrooms, 4 beds

19–24 Aug

$15,714 SGD for 5 nights

5.0 out of 5 average rating, 6 reviews

Top guest favourite

Guest suite in Oak Bluffs

Quiet Hide Away

1 bedroom, 1 queen bed

23–28 Aug

$2,933 SGD for 5 nights

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Free cancellation

4.98 out of 5 average rating, 200 reviews

Guest favourite

Home in Oak Bluffs

MV Sea Glenn Flower

4 bedrooms, 6 beds

23–28 Aug

$5,783 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 5 reviews