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

Photo 1 of 29

Apartment in Oak Bluffs

Island Inn - Studio Suite - 23F - Oak Bluffs, MA

1 bedroom, 2 beds, 1 private bathroom

1–6 Oct

$3,379 SGD for 5 nights

,

5.0 out of 5 average rating, 4 reviews

Photo 1 of 19

Featured hotel

Hotel in Oak Bluffs

Summercamp, Water view double queen

1 bedroom, 2 queen beds, 1 bathroom

23–28 Apr

$1,525 SGD for 5 nights

+$228 SGD Airbnb credit

Photo 1 of 29

Featured hotel

Hotel in Oak Bluffs

Nashua Suite

3 bedrooms, 1 bathroom

4–9 Oct

$2,863 SGD for 5 nights

+$429 SGD Airbnb credit

New place to stay

Photo 1 of 29

Home in Oak Bluffs

Near Farm Neck Golf | Outdoor Shower & Deck

3 bedrooms, 5 beds, 2 bathrooms

12–17 Oct

Free cancellation

New place to stay

Photo 1 of 25

Guest favourite

Guest suite in Oak Bluffs

Lovely 2 BR Oak Bluffs Apartment

2 bedrooms, 2 double beds, 1 bathroom

18–23 Oct

4.95 out of 5 average rating, 442 reviews

Photo 1 of 29

Guest favourite

Home in Oak Bluffs

Oak Bluffs Victorian Walk to Town & Beaches

5 bedrooms, 7 beds, 5.5 bathrooms

1–6 Oct

4.82 out of 5 average rating, 73 reviews

Photo 1 of 29

Guest favourite

Home in Oak Bluffs

New Home Walk to Town & Beaches

4 bedrooms, 4 queen beds, 2.5 bathrooms

1–6 Nov

Free cancellation

5.0 out of 5 average rating, 11 reviews

Photo 1 of 8

Guest favourite

Cabin in Oak Bluffs

Newly built rustic cabin in Oak Bluffs

1 bedroom, 1 bed, 1 bathroom

18–23 Oct

Free cancellation

4.85 out of 5 average rating, 27 reviews

Photo 1 of 29

Guest favourite

Home in Oak Bluffs

**Vineyard Vacation Retreat** -3 BR

3 bedrooms, 3 beds, 2 bathrooms

1–6 Oct

4.96 out of 5 average rating, 140 reviews

Photo 1 of 28

Top guest favourite

Home in Oak Bluffs

The Blue Lagoon, Oak Bluffs

3 bedrooms, 3 king beds, 3 bathrooms

11–16 Oct

4.98 out of 5 average rating, 57 reviews

Photo 1 of 20

Top guest favourite

Home in Oak Bluffs

Charming Oak Bluffs Retreat

6 bedrooms, 11 beds, 2.5 bathrooms

5–10 Oct

4.97 out of 5 average rating, 35 reviews

Photo 1 of 21

Guest favourite

Home in Oak Bluffs

Studio apt in newly built barn

2 beds, 1 bathroom

12–17 Oct

$1,612 SGD for 5 nights

4.94 out of 5 average rating, 528 reviews

Photo 1 of 19

Top guest favourite

Home in Oak Bluffs

Oak Bluffs Retreat, Walk to Town, Harbor, Ferries

3 bedrooms, 3 beds, 2 bathrooms

1–6 Oct

$5,668 SGD for 5 nights

5.0 out of 5 average rating, 18 reviews

Photo 1 of 29

Guest favourite

Home in Oak Bluffs

Modern farmhouse w/Pool and AC

4 bedrooms, 6 beds, 3.5 bathrooms

17–24 Oct

$7,970 SGD for 7 nights

5.0 out of 5 average rating, 18 reviews

Photo 1 of 6

Room in Oak Bluffs

Oak Bluffs Studio Walk to Beach - harbor & Ferry

1 queen bed, 1 bathroom

1–6 Oct

$1,613 SGD for 5 nights

Free cancellation

New place to stay

Photo 1 of 25

Top guest favourite

Home in Oak Bluffs

Updated cottage/ ocean views

3 bedrooms, 4 beds, 1.5 bathrooms

4–9 Oct

$3,351 SGD for 5 nights

5.0 out of 5 average rating, 28 reviews

Photo 1 of 29

Top guest favourite

Home in Oak Bluffs

*NEW* 3 min drive to OB Circuit ave

5 bedrooms, 6 beds, 2 bathrooms

1–6 Oct

$5,158 SGD for 5 nights

5.0 out of 5 average rating, 23 reviews

Photo 1 of 29

Guest favourite

Home in Oak Bluffs

impeccable cottage STEPS to downtown OB & beach!

3 bedrooms, 6 beds, 1 bathroom

19–24 Oct

$3,188 SGD for 5 nights

4.92 out of 5 average rating, 213 reviews

Photo 1 of 29

Superhost

Home in Oak Bluffs

Beach home just 0.8 miles to Farm Neck Golf Club!

3 bedrooms, 4 beds, 2 bathrooms

4–9 Oct

$3,369 SGD for 5 nights

Free cancellation

4.79 out of 5 average rating, 142 reviews