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Search results; Over 1,000 homes in Oak Bluffs

Top guest favourite

Home in Oak Bluffs

**Vineyard Vacation Retreat** -3 BR

3 bedrooms, 3 beds, 2 private bathrooms

8–13 Sept

$6,512 SGD for 5 nights

,

4.96 out of 5 average rating, 125 reviews

Top guest favourite

Guest suite in Oak Bluffs

Lovely 2 BR Oak Bluffs Apartment

2 bedrooms, 2 double beds

18–23 Oct

$1,249 SGD for 5 nights

4.95 out of 5 average rating, 424 reviews

Guest favourite

Home in Oak Bluffs

The Luxury Vineyard Yurt

2 bedrooms, 3 queen beds

16–21 Oct

$2,586 SGD for 5 nights

4.93 out of 5 average rating, 309 reviews

Top guest favourite

Home in Oak Bluffs

Pinkletink Plantation

3 bedrooms, 5 beds

10–15 Oct

$3,810 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 52 reviews

Home in Oak Bluffs

OB Salt & Cedar Cottage

4 bedrooms, 9 beds

24–31 Aug

$11,250 SGD for 7 nights

5.0 out of 5 average rating, 3 reviews

Top guest favourite

Home in Oak Bluffs

Charming Oak Bluffs Retreat

6 bedrooms, 11 beds

27 Sept – 2 Oct

$5,790 SGD for 5 nights

4.96 out of 5 average rating, 26 reviews

Guest favourite

Home in Oak Bluffs

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

3 bedrooms, 5 beds

28 Aug – 4 Sept

$7,431 SGD for 7 nights

4.92 out of 5 average rating, 12 reviews

Top guest favourite

Cottage in Oak Bluffs

The WestLake

4 bedrooms, 5 beds

26 Sept – 1 Oct

$5,270 SGD for 5 nights

5.0 out of 5 average rating, 10 reviews

Superhost

Home in Oak Bluffs

NEW! Charming Oak Bluffs Cottage - Sleeps 8

3 bedrooms, 4 beds

16–21 Jul

New place to stay

Top guest favourite

Home in Oak Bluffs

Updated cottage/ ocean views

3 bedrooms, 4 beds

27 Sept – 2 Oct

$4,099 SGD for 5 nights

5.0 out of 5 average rating, 21 reviews

Home in Oak Bluffs

Brand new! MV summer home!

3 bedrooms, 3 beds

14–19 Jul

$6,906 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Cabin in Oak Bluffs

Newly built rustic cabin in Oak Bluffs

1 bedroom, 1 bed

21–26 Jul

$2,096 SGD for 5 nights

Free cancellation

New place to stay

Guest favourite

Home in Oak Bluffs

Modern farmhouse w/Pool and AC

4 bedrooms, 6 beds

27 Sept – 2 Oct

$7,238 SGD for 5 nights

5.0 out of 5 average rating, 16 reviews

Top guest favourite

Home in Oak Bluffs

Charming 3 bedroom home in O.B.

3 bedrooms, 4 beds

23–28 Aug

$5,943 SGD for 5 nights

5.0 out of 5 average rating, 15 reviews

Guest favourite

Home in Oak Bluffs

impeccable cottage STEPS to downtown OB & beach!

3 bedrooms, 6 beds

20–25 Sept

$4,727 SGD for 5 nights

4.92 out of 5 average rating, 209 reviews

Superhost

Place to stay in Oak Bluffs

Oak Bluffs Circuit Av Walk Everywhere Single Room

1 bedroom, 7 beds

11–16 Sept

$1,337 SGD for 5 nights

Guest favourite

Home in Oak Bluffs

New Pristine Luxury Home on Martha's Vineyard

3 bedrooms, 6 beds

29 Sept – 4 Oct

$5,642 SGD for 5 nights

4.98 out of 5 average rating, 81 reviews

Top guest favourite

Home in Oak Bluffs

** Vineyard Vacation Retreat ** with HOT TUB

2 bedrooms, 2 beds

19–24 Sept

4.92 out of 5 average rating, 144 reviews

Home in Oak Bluffs

Walk to Beach! Oak Bluffs Home & Studio

4 bedrooms, 6 beds

29 Aug – 3 Sept

$3,609 SGD for 5 nights

New place to stay