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

Guest favourite

Boutique hotel in Oak Bluffs

Porch Room 1 queen bed

1 bedroom, 1 bed, 1 private bathroom

24–29 Aug

$3,895 SGD for 5 nights

,

4.89 out of 5 average rating, 53 reviews

Top guest favourite

Home in Oak Bluffs

Spectacular beach & pool combo; beautiful sunsets!

4 bedrooms, 5 beds

4–9 Oct

$4,220 SGD for 5 nights

4.93 out of 5 average rating, 221 reviews

Superhost

Bed and breakfast in Oak Bluffs

Private Suite | Spectacular Harbor Views | OB

1 bedroom, 1 queen bed

19–24 Aug

$4,185 SGD for 5 nights

Pay $0 today

Free cancellation

New place to stay

Top guest favourite

Cottage in Oak Bluffs

The WestLake

4 bedrooms, 5 beds

3–8 Oct

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 12 reviews

Guest favourite

Home in Oak Bluffs

New Pristine Luxury Home on Martha's Vineyard

3 bedrooms, 6 beds

31 Aug – 5 Sept

Pay $0 today

Free cancellation

4.98 out of 5 average rating, 87 reviews

Top guest favourite

Home in Oak Bluffs

The Blue Lagoon, Oak Bluffs

3 bedrooms, 3 king beds

27 Sept – 2 Oct

4.98 out of 5 average rating, 54 reviews

Top guest favourite

Guest suite in Oak Bluffs

Quiet Hide Away

1 bedroom, 1 queen bed

22–27 Aug

Pay $0 today

Free cancellation

4.98 out of 5 average rating, 203 reviews

Villa in Oak Bluffs

Luxury! Heated Pool & Spa!Tennis! Firepit! Hammock

5 bedrooms, 7 beds

30 Aug – 4 Sept

Pay $0 today

Free cancellation

4.65 out of 5 average rating, 17 reviews

Guest favourite

Home in Oak Bluffs

East Chop Oceanview Escape

6 bedrooms, 8 beds

21–27 Aug

$29,703 SGD for 6 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 5 reviews

Superhost

Home in Oak Bluffs

Oak Bluffs 4BR • 5 Min Drive to Downtown

4 bedrooms, 4 beds

27 Sept – 2 Oct

Pay $0 today

Free cancellation

4.88 out of 5 average rating, 68 reviews

Top guest favourite

Guest suite in Oak Bluffs

Lovely 2 BR Oak Bluffs Apartment

2 bedrooms, 2 double beds

18–23 Oct

$1,292 SGD for 5 nights

Pay $0 today

Free cancellation

4.95 out of 5 average rating, 432 reviews

Guest favourite

Home in Oak Bluffs

Sunny 3 bedroom with large deck, porch & kayaks

3 bedrooms, 5 beds

4–11 Jun

$6,273 SGD for 7 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 15 reviews

Top guest favourite

Home in Tisbury

Martha’s Vineyard Waterfront Private Beach

8 bedrooms, 10 beds

20–25 Sept

$16,956 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 18 reviews

Top guest favourite

Home in Oak Bluffs

The Luxury Vineyard Yurt

2 bedrooms, 3 queen beds

19–24 Oct

$2,559 SGD for 5 nights

4.93 out of 5 average rating, 317 reviews

Top guest favourite

Home in Oak Bluffs

**Vineyard Vacation Retreat** -3 BR

3 bedrooms, 3 beds

8–13 Sept

$6,443 SGD for 5 nights

4.96 out of 5 average rating, 133 reviews

Top guest favourite

Home in Oak Bluffs

*NEW* 3 min drive to OB Circuit ave

5 bedrooms, 6 beds

30 Aug – 4 Sept

$7,305 SGD for 5 nights

5.0 out of 5 average rating, 22 reviews

Home in Oak Bluffs

Amanda’s Veranda

4 bedrooms, 5 beds

27 Sept – 2 Oct

Pay $0 today

Free cancellation

New place to stay

Top guest favourite

Home in Oak Bluffs

Charming Oak Bluffs Retreat

6 bedrooms, 11 beds

27 Sept – 2 Oct

Pay $0 today

Free cancellation

4.97 out of 5 average rating, 32 reviews

Guest favourite

Home in Oak Bluffs

MV Sea Glenn Flower

4 bedrooms, 6 beds

23–28 Aug

$5,906 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 5 reviews