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Search results; Over 1,000 homes in Oak Bluffs

Top guest favourite

Guest suite in Oak Bluffs

Sea View Waterfront Beachfront Apartment

1 bedroom, 1 bed, 1 private bathroom

30 Aug – 4 Sept

$3,497 SGD for 5 nights

,

4.97 out of 5 average rating, 135 reviews

Home in Oak Bluffs

Amanda’s Veranda

4 bedrooms, 5 beds, 3.5 bathrooms

30 Aug – 4 Sept

$6,797 SGD for 5 nights

New place to stay

Home in Oak Bluffs

Oak Bluffs Summer Home

3 bedrooms, 4 beds, 2 bathrooms

5–10 Sept

$5,865 SGD for 5 nights

Pay $0 today

Free cancellation

New place to stay

Home in Oak Bluffs

MV Sea Glenn Flower

4 bedrooms, 6 beds, 3 bathrooms

23–28 Aug

$5,794 SGD for 5 nights

5.0 out of 5 average rating, 4 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

$10,572 SGD for 5 nights

4.83 out of 5 average rating, 66 reviews

Top guest favourite

Cottage in Oak Bluffs

The WestLake

4 bedrooms, 5 beds, 2 bathrooms

3–8 Oct

$5,232 SGD for 5 nights

5.0 out of 5 average rating, 12 reviews

Top guest favourite

Home in Oak Bluffs

The Luxury Vineyard Yurt

2 bedrooms, 3 queen beds, 1 bathroom

19–24 Oct

$2,563 SGD for 5 nights

4.93 out of 5 average rating, 315 reviews

Top guest favourite

Home in Oak Bluffs

**Vineyard Vacation Retreat** -3 BR

3 bedrooms, 3 beds, 2 bathrooms

8–13 Sept

$6,454 SGD for 5 nights

4.96 out of 5 average rating, 130 reviews

Home in Oak Bluffs

Newly restored cottage in downtown Oak Bluffs!

3 bedrooms, 7 beds, 1 bathroom

13–18 Sept

$4,446 SGD for 5 nights

Free cancellation

New place to stay

Top guest favourite

Home in Oak Bluffs

Charming 3-Bedrm w/Loft.New Construct! Walk 2 town

3 bedrooms, 5 beds, 3.5 bathrooms

22–29 Aug

Weekly discount

5.0 out of 5 average rating, 18 reviews

Guest favourite

Cottage in Oak Bluffs

111H Beautiful clean walk to Town, Inkwell, harbor

1 bedroom, 2 beds, 1.5 bathrooms

13–18 Sept

$4,071 SGD for 5 nights

4.95 out of 5 average rating, 194 reviews

Top guest favourite

Home in Oak Bluffs

Casa Luca| Serene 3BR| SunRm, Outdr Shwr, A/C, BBQ

3 bedrooms, 5 beds, 1 bathroom

28 Aug – 4 Sept

$7,365 SGD for 7 nights

4.94 out of 5 average rating, 17 reviews

Top guest favourite

Home in Oak Bluffs

Pinkletink Plantation

3 bedrooms, 5 beds, 2.5 bathrooms

16–21 Oct

Pay $0 today

Free cancellation

4.98 out of 5 average rating, 54 reviews

Guest favourite

Home in Oak Bluffs

New Home Walk to Town & Beaches

4 bedrooms, 4 queen beds, 2.5 bathrooms

7–12 Sept

$11,567 SGD for 5 nights

5.0 out of 5 average rating, 7 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, 427 reviews

Superhost

Home in Oak Bluffs

Cozy, Central Island Family Home

5 bedrooms, 7 beds, 2 bathrooms

26 Jul – 1 Aug

$6,248 SGD for 6 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 3 reviews

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

$5,592 SGD for 5 nights

4.98 out of 5 average rating, 86 reviews

Guest favourite

Home in Oak Bluffs

New Serenity Retreat

2 bedrooms, 3 beds, 1.5 bathrooms

29 Aug – 3 Sept

$5,034 SGD for 5 nights

5.0 out of 5 average rating, 7 reviews

Top guest favourite

Home in Oak Bluffs

*NEW* 3 min drive to OB Circuit ave

5 bedrooms, 6 beds, 2 bathrooms

30 Aug – 4 Sept

$7,317 SGD for 5 nights

5.0 out of 5 average rating, 22 reviews