We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Search results; Over 1,000 homes in Oak Bluffs

Nature lodge in Oak Bluffs

Lovely King-sized guest room in beautiful home

1 bedroom, 1 bed, 1 shared bathroom

9–14 Jul

$2,821 SGD for 5 nights

,

4.88 out of 5 average rating, 18 reviews

Superhost

Home in Oak Bluffs

NEW! Charming Oak Bluffs Cottage - Sleeps 8

3 bedrooms, 4 beds, 2 bathrooms

16–21 Jul

New place to stay

Guest favourite

Home in Oak Bluffs

The Luxury Vineyard Yurt

2 bedrooms, 3 queen beds, 1 bathroom

16–21 Oct

$2,588 SGD for 5 nights

4.93 out of 5 average rating, 308 reviews

Guest favourite

Cottage in Oak Bluffs

Beautiful clean walk to Town, Inkwell and harbor!

1 bedroom, 2 beds, 1.5 bathrooms

22–27 Jul

$4,119 SGD for 5 nights

4.95 out of 5 average rating, 189 reviews

Guest favourite

Guest suite in Oak Bluffs

Cottage suite between the harbors: no minimum stay

2 bedrooms, 3 beds, 1 bathroom

19–24 Jul

4.79 out of 5 average rating, 341 reviews

Place to stay in Oak Bluffs

Oak Bluffs Cottage Walk To Town

1 bedroom, 2 double beds, 1 bathroom

8–15 Aug

$16,315 SGD for 7 nights

Guest favourite

Flat in Oak Bluffs

14C Kennebec THE center of OB! No car, No problem!

1 bedroom, 2 beds, 1 bathroom

2–7 Aug

5.0 out of 5 average rating, 19 reviews

Top guest favourite

Home in Oak Bluffs

**Vineyard Vacation Retreat** -3 BR

3 bedrooms, 3 beds, 2 bathrooms

8–13 Sept

$6,516 SGD for 5 nights

4.96 out of 5 average rating, 125 reviews

Guest favourite

Home in Oak Bluffs

New Pristine Luxury Home on Martha's Vineyard

3 bedrooms, 6 beds, 2.5 bathrooms

29 Sept – 4 Oct

$5,795 SGD for 5 nights

4.98 out of 5 average rating, 81 reviews

Guest favourite

Home in Oak Bluffs

Oak Bluffs Victorian Walk to Town & Beaches

5 bedrooms, 7 beds, 5.5 bathrooms

18–23 Sept

$9,301 SGD for 5 nights

4.83 out of 5 average rating, 65 reviews

Superhost

Home in Oak Bluffs

Quintessential 1920s renovated bungalow new 2026!

2 bedrooms, 2 beds, 1.5 bathrooms

23–28 Jul

$5,822 SGD for 5 nights

New place to stay

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

$7,436 SGD for 7 nights

4.92 out of 5 average rating, 12 reviews

Top guest favourite

Cottage in Oak Bluffs

Beautiful and walk to everything Oak Bluffs!

1 bedroom, 2 beds, 1.5 bathrooms

22–27 Aug

$6,473 SGD for 5 nights

4.97 out of 5 average rating, 181 reviews

Guest favourite

Apartment in Oak Bluffs

Stunning. Walk to Beach, Town and Harbor 113B

1 bedroom, 1 queen bed, 1 bathroom

31 Jul – 5 Aug

$7,027 SGD for 5 nights

4.9 out of 5 average rating, 264 reviews

Home in Oak Bluffs

Brand new! MV summer home!

3 bedrooms, 3 beds, 1 bathroom

14–19 Jul

$6,939 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Superhost

Place to stay in Oak Bluffs

Oak Bluffs Circuit Av Walk Everywhere Single Room

1 bedroom, 1 bed, 1 bathroom

10–15 Jul

$1,678 SGD for 5 nights

Superhost

Home in Oak Bluffs

Hidden home in the North Bluff

3 bedrooms, 3 beds, 3 bathrooms

6–11 Sept

$8,005 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Top guest favourite

Home in Oak Bluffs

Pinkletink Plantation

3 bedrooms, 5 beds, 2.5 bathrooms

10–15 Oct

$3,812 SGD for 5 nights

4.98 out of 5 average rating, 51 reviews

Superhost

Home in Oak Bluffs

Martha’s Vineyard Boutique Beach Cottage!

3 bedrooms, 6 beds, 2 bathrooms

26–31 Aug

$5,216 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews