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Search results; Over 1,000 homes in Oak Bluffs

Guest favourite

Apartment in Oak Bluffs

113B Cutest! Walk to Beach, Town and Harbor!

1 bedroom, 1 bed, 1 private bathroom

19–24 Aug

$7,335 SGD for 5 nights

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4.9 out of 5 average rating, 270 reviews

Home in Oak Bluffs

Perfect Vineyard Base: with backyard retreat.

3 bedrooms, 4 beds, 2 bathrooms

19–24 Aug

$6,794 SGD for 5 nights

New place to stay

Top guest favourite

Cottage in Oak Bluffs

111I Beautiful and walk to everything Oak Bluffs!

1 bedroom, 2 beds, 1.5 bathrooms

10–15 Aug

$15,022 SGD for 5 nights

4.97 out of 5 average rating, 184 reviews

Apartment in Oak Bluffs

Walk to Ferry & Beach from Central Oak Bluff

2 bedrooms, 3 beds, 1 bathroom

24–29 Aug

$5,102 SGD for 5 nights

New place to stay

Home in Oak Bluffs

Amanda’s Veranda

4 bedrooms, 5 beds, 3.5 bathrooms

30 Aug – 4 Sept

New place to stay

Top guest favourite

Cottage in Oak Bluffs

The WestLake

4 bedrooms, 5 beds, 2 bathrooms

3–8 Oct

$5,230 SGD for 5 nights

5.0 out of 5 average rating, 12 reviews

Superhost

Place to stay in Tisbury

Private room for 4 in quiet Vineyard Haven home

1 bedroom, 3 beds, 1 bathroom

20–25 Sept

Pay $0 today

Free cancellation

New place to stay

Guest favourite

Home in Oak Bluffs

Modern cabin in the woods.

3 bedrooms, 4 beds, 1.5 bathrooms

1–6 Sept

$4,266 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 7 reviews

Home in Oak Bluffs

Oak Bluffs Summer Home

3 bedrooms, 4 beds, 2 bathrooms

30 Aug – 4 Sept

$6,362 SGD for 5 nights

Pay $0 today

Free cancellation

New place to stay

Guest favourite

Home in Oak Bluffs

New Pristine Luxury Home on Martha's Vineyard

3 bedrooms, 6 beds, 2.5 bathrooms

31 Aug – 5 Sept

$5,590 SGD for 5 nights

4.98 out of 5 average rating, 86 reviews

Home in Oak Bluffs

East Chop Oceanview Escape

6 bedrooms, 8 beds, 4.5 bathrooms

21–27 Aug

$26,844 SGD for 6 nights

5.0 out of 5 average rating, 4 reviews

Top guest favourite

Home in Tisbury

Martha’s Vineyard Waterfront Private Beach

8 bedrooms, 10 beds, 5.5 bathrooms

20–25 Sept

$16,851 SGD for 5 nights

5.0 out of 5 average rating, 18 reviews

Guest favourite

Home in Oak Bluffs

Oak Bluffs Victorian Walk to Town & Beaches

5 bedrooms, 7 beds, 5.5 bathrooms

29 Sept – 4 Oct

$10,569 SGD for 5 nights

4.82 out of 5 average rating, 67 reviews

Guest favourite

Guest suite in Oak Bluffs

Lovely 2 BR Oak Bluffs Apartment

2 bedrooms, 2 double beds, 1 bathroom

18–23 Oct

$1,238 SGD for 5 nights

4.95 out of 5 average rating, 428 reviews

Top guest favourite

Home in Oak Bluffs

The Luxury Vineyard Yurt

2 bedrooms, 3 queen beds, 1 bathroom

19–24 Oct

$2,562 SGD for 5 nights

4.93 out of 5 average rating, 316 reviews

Home in Oak Bluffs

MV Sea Glenn Flower

4 bedrooms, 6 beds, 3 bathrooms

23–28 Aug

$5,792 SGD for 5 nights

5.0 out of 5 average rating, 5 reviews

Featured hotel

Room in Oak Bluffs

Water view double queen

2 queen beds, 1 bathroom

12–17 Sept

$2,822 SGD for 5 nights

+$423 SGD Airbnb credit

Top guest favourite

Home in Oak Bluffs

Spectacular beach & pool combo; beautiful sunsets!

4 bedrooms, 5 beds, 5.5 bathrooms

4–9 Oct

$4,341 SGD for 5 nights

4.93 out of 5 average rating, 221 reviews

Guest favourite

Home in Oak Bluffs

New Serenity Retreat

2 bedrooms, 3 beds, 1.5 bathrooms

29 Aug – 3 Sept

$5,032 SGD for 5 nights

5.0 out of 5 average rating, 7 reviews