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
Top guest favourite
Guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
2 bedrooms
,
·
3 beds
,
·
1 private 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)
Room in Oak Bluffs
Oak Bluffs Cottage Walk To Town
2 double beds
2 double beds
8–15 Aug
8–15 Aug
$10,973 SGD
Show price breakdown
for 7 nights
$10,973 SGD for 7 nights
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
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
Flat in Oak Bluffs
111C Beautiful private condo walk to everything!
1 bedroom
1 bedroom
,
·
2 beds
2 beds
16–21 Aug
16–21 Aug
$9,403 SGD
Show price breakdown
for 5 nights
$9,403 SGD for 5 nights
4.95 out of 5 average rating, 195 reviews
4.95 (195)
Guest favourite
Guest favourite
Cottage in Oak Bluffs
111H Beautiful clean walk to Town, Inkwell, harbor
1 bedroom
1 bedroom
,
·
2 beds
2 beds
30 Aug – 4 Sept
30 Aug – 4 Sept
$4,412 SGD
Show price breakdown
for 5 nights
$4,412 SGD for 5 nights
4.95 out of 5 average rating, 193 reviews
4.95 (193)
Cabin in Oak Bluffs
Newly built rustic cabin in Oak Bluffs
1 bedroom
1 bedroom
,
·
1 bed
1 bed
30 Aug – 4 Sept
30 Aug – 4 Sept
$2,000 SGD
Show price breakdown
for 5 nights
$2,000 SGD for 5 nights
Free cancellation
New place to stay
New
Guest favourite
Guest favourite
Guest suite in Oak Bluffs
Cottage suite between the harbors: no minimum stay
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
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)
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
18–23 Oct
18–23 Oct
$1,249 SGD
Show price breakdown
for 5 nights
$1,249 SGD for 5 nights
4.95 out of 5 average rating, 426 reviews
4.95 (426)
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
2–7 Aug
2–7 Aug
$6,903 SGD
$6,124 SGD
Show price breakdown
for 5 nights
4.93 out of 5 average rating, 15 reviews
4.93 (15)
Home in Oak Bluffs
MV Sea Glenn Flower
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
23–28 Aug
23–28 Aug
$5,847 SGD
Show price breakdown
for 5 nights
$5,847 SGD for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Top guest favourite
Guest favourite
Flat in Oak Bluffs
14A Kennebec THE center of OB! No car, No problem!
1 bedroom
1 bedroom
,
·
2 beds
2 beds
17–22 Aug
17–22 Aug
$13,863 SGD
$10,812 SGD
Show price breakdown
for 5 nights
4.97 out of 5 average rating, 32 reviews
4.97 (32)
Home in Oak Bluffs
Oak Bluffs Oasis. Walk to town, beach & ferry.
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
7–12 Sept
7–12 Sept
$5,525 SGD
Show price breakdown
for 5 nights
$5,525 SGD for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Flat in Oak Bluffs
Island Oasis
1 bedroom
1 bedroom
,
·
3 beds
3 beds
2–7 Aug
2–7 Aug
$4,801 SGD
Show price breakdown
for 5 nights
$4,801 SGD for 5 nights
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Top guest favourite
Guest favourite
Home in Oak Bluffs
Pinkletink Plantation
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
10–15 Oct
10–15 Oct
$3,714 SGD
$3,313 SGD
Show price breakdown
for 5 nights
Free cancellation
4.98 out of 5 average rating, 53 reviews
4.98 (53)
Top guest favourite
Guest favourite
139
Reviews
4.94
Stars
Rating
10
Years hosting
Room in Tisbury
Vineyard Haven Sanctuary- free bikes!
1 queen bed
1 queen bed
13–18 Sept
13–18 Sept
$1,339 SGD
Show price breakdown
for 5 nights
$1,339 SGD for 5 nights
4.94 out of 5 average rating, 139 reviews
4.94 (139)
Guest favourite
Guest favourite
Home in Oak Bluffs
New Serenity Retreat
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
1–6 Aug
1–6 Aug
$8,923 SGD
Show price breakdown
for 5 nights
$8,923 SGD for 5 nights
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
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)
Home in Oak Bluffs
East Chop Oceanview Escape
6 bedrooms
6 bedrooms
,
·
8 beds
8 beds
21–27 Aug
21–27 Aug
$27,097 SGD
Show price breakdown
for 6 nights
$27,097 SGD for 6 nights
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Home in Oak Bluffs
Just listed! Bright, cozy, quiet & full of charm
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
20–25 Aug
20–25 Aug
$6,782 SGD
Show price breakdown
for 5 nights
$6,782 SGD for 5 nights
5.0 out of 5 average rating, 4 reviews
5.0 (4)
1
2
3
4
…
15