Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
NEW
NEW
Experiences
Experiences, new
NEW
NEW
Services
Services, new
Start your search
Location
Homes in Oak Bluffs
Check in / Check out
Any week
Guests
Add guests
Become a host
Help Centre
Become a host
It’s easy to start hosting and earn extra income.
Refer a host
Find a co-host
Log in or sign up
filters
Filters
Price
Type of place
Show map
Search results; Over 1,000 homes in Oak Bluffs
Over 1,000 homes in Oak Bluffs
Guest favourite
Guest favourite
Guest suite in Oak Bluffs
Cottage suite between the harbors: no minimum stay
2 bedrooms
,
·
3 beds
,
·
1 private bathroom
29 Aug – 3 Sept
29 Aug – 3 Sept
$4,495 SGD
$3,874 SGD
Show price breakdown
for 5 nights
,
·
4.79 out of 5 average rating, 347 reviews
4.79 (347)
Room in Oak Bluffs
Oak Bluffs Cottage Walk To Town
2 double beds
2 double beds
,
·
1 bathroom
1 bathroom
8–15 Aug
8–15 Aug
$10,973 SGD
Show price breakdown
for 7 nights
$10,973 SGD for 7 nights
Free cancellation
Guest favourite
Guest favourite
Cottage in Oak Bluffs
111H Beautiful clean walk to Town, Inkwell, harbor
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1.5 bathrooms
1.5 bathrooms
13–18 Sept
13–18 Sept
$4,108 SGD
Show price breakdown
for 5 nights
$4,108 SGD for 5 nights
4.95 out of 5 average rating, 193 reviews
4.95 (193)
Top guest favourite
Guest favourite
Home in Oak Bluffs
Casa Luca| Serene 3BR| SunRm, Outdr Shwr, A/C, BBQ
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
1 bathroom
1 bathroom
2–7 Aug
2–7 Aug
$6,903 SGD
$5,994 SGD
Show price breakdown
for 5 nights
Free cancellation
4.93 out of 5 average rating, 15 reviews
4.93 (15)
Top guest favourite
Guest favourite
Home in Oak Bluffs
113A Walk to Town, beach and amazing location!
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1.5 bathrooms
1.5 bathrooms
16–21 Aug
16–21 Aug
$10,751 SGD
$9,518 SGD
Show price breakdown
for 5 nights
4.95 out of 5 average rating, 213 reviews
4.95 (213)
Top guest favourite
Guest favourite
Cottage in Oak Bluffs
111I Beautiful and walk to everything Oak Bluffs!
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1.5 bathrooms
1.5 bathrooms
22–27 Aug
22–27 Aug
$5,784 SGD
Show price breakdown
for 5 nights
$5,784 SGD for 5 nights
4.97 out of 5 average rating, 183 reviews
4.97 (183)
Cabin in Oak Bluffs
Newly built rustic cabin in Oak Bluffs
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
30 Aug – 4 Sept
30 Aug – 4 Sept
$2,000 SGD
Show price breakdown
for 5 nights
$2,000 SGD for 5 nights
Pay $0 today
Free cancellation
New place to stay
New
Home in Oak Bluffs
MV Sea Glenn Flower
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
3 bathrooms
3 bathrooms
23–28 Aug
23–28 Aug
$5,847 SGD
Show price breakdown
for 5 nights
$5,847 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Home in Oak Bluffs
Oak Bluffs Oasis. Walk to town, beach & ferry.
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
7–12 Sept
7–12 Sept
$5,525 SGD
Show price breakdown
for 5 nights
$5,525 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Top guest favourite
Guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
2 bedrooms
2 bedrooms
,
·
3 queen beds
3 queen beds
,
·
1 bathroom
1 bathroom
16–21 Oct
16–21 Oct
$2,586 SGD
Show price breakdown
for 5 nights
$2,586 SGD for 5 nights
4.93 out of 5 average rating, 313 reviews
4.93 (313)
Top guest favourite
Guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
2 bedrooms
2 bedrooms
,
·
2 double beds
2 double beds
,
·
1 bathroom
1 bathroom
18–23 Oct
18–23 Oct
$1,249 SGD
Show price breakdown
for 5 nights
$1,249 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 426 reviews
4.95 (426)
Flat in Oak Bluffs
Island Oasis
1 bedroom
1 bedroom
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
2–7 Aug
2–7 Aug
$4,801 SGD
Show price breakdown
for 5 nights
$4,801 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Top guest favourite
Guest favourite
Flat in Oak Bluffs
14D Kennebec THE center of OB! No car, No problem!
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
16–21 Aug
16–21 Aug
$10,812 SGD
Show price breakdown
for 5 nights
$10,812 SGD for 5 nights
4.94 out of 5 average rating, 32 reviews
4.94 (32)
Top guest favourite
Guest favourite
Room in Tisbury
Vineyard Haven Sanctuary- free bikes!
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
13–18 Sept
13–18 Sept
$1,339 SGD
Show price breakdown
for 5 nights
$1,339 SGD for 5 nights
Free cancellation
4.94 out of 5 average rating, 139 reviews
4.94 (139)
Top guest favourite
Guest favourite
Home in Oak Bluffs
Pinkletink Plantation
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2.5 bathrooms
2.5 bathrooms
10–15 Oct
10–15 Oct
$3,714 SGD
$3,313 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
4.98 out of 5 average rating, 53 reviews
4.98 (53)
Home in Oak Bluffs
East Chop Oceanview Escape
6 bedrooms
6 bedrooms
,
·
8 beds
8 beds
,
·
4.5 bathrooms
4.5 bathrooms
21–27 Aug
21–27 Aug
$27,097 SGD
Show price breakdown
for 6 nights
$27,097 SGD for 6 nights
Free cancellation
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Guest favourite
Guest favourite
Tiny home in Oak Bluffs
Delightful 1BR House near all! Walk to beach.
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
1–6 Aug
1–6 Aug
$4,001 SGD
Show price breakdown
for 5 nights
$4,001 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 9 reviews
5.0 (9)
Guest favourite
Guest favourite
Home in Oak Bluffs
New Serenity Retreat
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1.5 bathrooms
1.5 bathrooms
1–6 Aug
1–6 Aug
$8,923 SGD
Show price breakdown
for 5 nights
$8,923 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Top guest favourite
Guest favourite
Home in Oak Bluffs
Walk East Chop from Dover House
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
,
·
4.5 bathrooms
4.5 bathrooms
21–26 Sept
21–26 Sept
$10,668 SGD
Show price breakdown
for 5 nights
$10,668 SGD for 5 nights
5.0 out of 5 average rating, 33 reviews
5.0 (33)
1
2
3
4
…
15
