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
Cottage in Oak Bluffs
East Chop Cottage - walk to lighthouse & beach!
1 bedroom
,
·
1 bed
,
·
0.5 private bathroom
25–30 Aug
25–30 Aug
$3,256 SGD
Show price breakdown
for 5 nights
$3,256 SGD for 5 nights
,
·
4.9 out of 5 average rating, 143 reviews
4.9 (143)
Featured hotel
Featured hotel
1
Review
5.0
Stars
Rating
2
Years hosting
Hotel in Oak Bluffs
Water view double queen
1 bedroom
1 bedroom
,
·
2 queen beds
2 queen beds
16–21 Sept
16–21 Sept
$3,981 SGD
Show price breakdown
for 5 nights
$3,981 SGD for 5 nights
+$597 SGD Airbnb credit
Pay $0 today
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
$1,281 SGD
Show price breakdown
for 5 nights
$1,281 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 423 reviews
4.95 (423)
Guest favourite
Guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
2 bedrooms
2 bedrooms
,
·
3 queen beds
3 queen beds
16–21 Oct
16–21 Oct
$2,588 SGD
Show price breakdown
for 5 nights
$2,588 SGD for 5 nights
4.93 out of 5 average rating, 308 reviews
4.93 (308)
Guest favourite
Guest favourite
Cottage in Oak Bluffs
Oak Bluffs, Martha's Vineyard; Gingerbread House
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
12–19 Jul
12–19 Jul
$7,640 SGD
$7,005 SGD
Show price breakdown
for 7 nights
Free cancellation
4.88 out of 5 average rating, 16 reviews
4.88 (16)
Top guest favourite
Guest favourite
Guest house in Oak Bluffs
Oak bluffs cottage Perfect place to honeymoon!
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
18–23 Oct
18–23 Oct
$2,097 SGD
Show price breakdown
for 5 nights
$2,097 SGD for 5 nights
Pay $0 today
Free cancellation
4.97 out of 5 average rating, 132 reviews
4.97 (132)
Cabin in Oak Bluffs
Newly built cabin walking distance from Oak Bluffs
1 bedroom
1 bedroom
,
·
1 bed
1 bed
21–26 Jul
21–26 Jul
$2,301 SGD
Show price breakdown
for 5 nights
$2,301 SGD for 5 nights
Pay $0 today
Free cancellation
New place to stay
New
Guest favourite
Guest favourite
Home in Oak Bluffs
Studio apt in newly built barn
2 beds
2 beds
27 Sept – 2 Oct
27 Sept – 2 Oct
$1,601 SGD
Show price breakdown
for 5 nights
$1,601 SGD for 5 nights
Free cancellation
4.94 out of 5 average rating, 511 reviews
4.94 (511)
Superhost
Superhost
Home in Oak Bluffs
NEW! Charming Oak Bluffs Cottage - Sleeps 8
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
16–21 Jul
16–21 Jul
$8,022 SGD
$6,752 SGD
Show price breakdown
for 5 nights
Free cancellation
New place to stay
New
Guest favourite
Guest favourite
104
Reviews
4.9
Stars
Rating
10
Years hosting
Room in Oak Bluffs
Oak Bluffs/ Harbor Views/ Queen Bed/ In Town
1 queen bed
1 queen bed
30 Aug – 4 Sept
30 Aug – 4 Sept
$2,257 SGD
Show price breakdown
for 5 nights
$2,257 SGD for 5 nights
Free cancellation
4.9 out of 5 average rating, 104 reviews
4.9 (104)
Guest favourite
Guest favourite
Guest house in Oak Bluffs
Sweet Summer Cottage
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
26–31 Jul
26–31 Jul
$2,459 SGD
Show price breakdown
for 5 nights
$2,459 SGD for 5 nights
4.92 out of 5 average rating, 65 reviews
4.92 (65)
Superhost
Superhost
Home in Oak Bluffs
Quintessential 1920s renovated bungalow new 2026!
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
23–28 Jul
23–28 Jul
$5,822 SGD
Show price breakdown
for 5 nights
$5,822 SGD for 5 nights
Free cancellation
New place to stay
New
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
20–25 Jul
20–25 Jul
$3,971 SGD
$3,407 SGD
Show price breakdown
for 5 nights
4.97 out of 5 average rating, 29 reviews
4.97 (29)
Top guest favourite
Guest favourite
Flat in Oak Bluffs
Beautiful private apartment walk to everything!
1 bedroom
1 bedroom
,
·
2 beds
2 beds
18–23 Jul
18–23 Jul
$3,510 SGD
$3,036 SGD
Show price breakdown
for 5 nights
4.95 out of 5 average rating, 194 reviews
4.95 (194)
Top guest favourite
Guest favourite
Guest suite in Oak Bluffs
Quiet Hide Away
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
12–17 Jul
12–17 Jul
$2,963 SGD
$2,478 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
4.98 out of 5 average rating, 196 reviews
4.98 (196)
Top guest favourite
Guest favourite
Flat in Oak Bluffs
Town/Beach: Vineyard Vacation Houses welcomes you!
1 bedroom
1 bedroom
,
·
2 beds
2 beds
15–20 Oct
15–20 Oct
$2,581 SGD
Show price breakdown
for 5 nights
$2,581 SGD for 5 nights
4.89 out of 5 average rating, 303 reviews
4.89 (303)
Top guest favourite
Guest favourite
154
Reviews
4.99
Stars
Rating
10
Years hosting
Room in Tisbury
Historic Captain's House. Walk to town and ferry
2 beds
2 beds
29 Sept – 4 Oct
29 Sept – 4 Oct
$1,423 SGD
Show price breakdown
for 5 nights
$1,423 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 154 reviews
4.99 (154)
Guest favourite
Guest favourite
Home in Oak Bluffs
Oak Bluffs | A/C, Outdoor Shower, Walk to Town
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
10–15 Jul
10–15 Jul
$6,404 SGD
Show price breakdown
for 5 nights
$6,404 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Home in Oak Bluffs
Amanda’s Veranda
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
17–22 Jul
17–22 Jul
$6,100 SGD
Show price breakdown
for 5 nights
$6,100 SGD for 5 nights
Free cancellation
New place to stay
New
1
2
3
4
…
15