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
Home in Oak Bluffs
The Luxury Vineyard Yurt
2 bedrooms
,
·
3 beds
,
·
1 private bathroom
16–21 Oct
16–21 Oct
$2,584 SGD
Show price breakdown
for 5 nights
$2,584 SGD for 5 nights
,
·
4.93 out of 5 average rating, 312 reviews
4.93 (312)
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
$5,877 SGD
Show price breakdown
for 5 nights
$5,877 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Top guest favourite
Guest favourite
Cottage in Oak Bluffs
The WestLake
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
3–8 Oct
3–8 Oct
$5,276 SGD
Show price breakdown
for 5 nights
$5,276 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 10 reviews
5.0 (10)
Guest favourite
Guest favourite
Cottage in Oak Bluffs
111G Beautiful walk to Town, Inkwell and harbor!
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1.5 bathrooms
1.5 bathrooms
24–29 Aug
24–29 Aug
$4,866 SGD
Show price breakdown
for 5 nights
$4,866 SGD for 5 nights
4.94 out of 5 average rating, 222 reviews
4.94 (222)
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
$10,805 SGD
Show price breakdown
for 5 nights
$10,805 SGD for 5 nights
4.94 out of 5 average rating, 32 reviews
4.94 (32)
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
30 Aug – 4 Sept
30 Aug – 4 Sept
$4,409 SGD
Show price breakdown
for 5 nights
$4,409 SGD for 5 nights
4.95 out of 5 average rating, 192 reviews
4.95 (192)
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
$8,917 SGD
Show price breakdown
for 5 nights
$8,917 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
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
$6,380 SGD
Show price breakdown
for 5 nights
$6,380 SGD 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
$10,743 SGD
$9,511 SGD
Show price breakdown
for 5 nights
4.95 out of 5 average rating, 213 reviews
4.95 (213)
Home in Oak Bluffs
OB Salt & Cedar Cottage
4 bedrooms
4 bedrooms
,
·
9 beds
9 beds
,
·
2 bathrooms
2 bathrooms
24–31 Aug
24–31 Aug
$10,045 SGD
Show price breakdown
for 7 nights
$10,045 SGD for 7 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Top guest favourite
Guest favourite
Home in Oak Bluffs
Spectacular beach & pool combo; beautiful sunsets!
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
5.5 bathrooms
5.5 bathrooms
4–9 Oct
4–9 Oct
$4,379 SGD
Show price breakdown
for 5 nights
$4,379 SGD for 5 nights
4.93 out of 5 average rating, 221 reviews
4.93 (221)
Home in Oak Bluffs
Oak Bluffs Oasis. Walk to town, beach & ferry.
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
22–28 Aug
22–28 Aug
$6,511 SGD
Show price breakdown
for 6 nights
$6,511 SGD for 6 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Top guest favourite
Guest favourite
Home in Tisbury
Martha’s Vineyard Waterfront Private Beach
8 bedrooms
8 bedrooms
,
·
10 beds
10 beds
,
·
5.5 bathrooms
5.5 bathrooms
20–25 Sept
20–25 Sept
$16,998 SGD
Show price breakdown
for 5 nights
$16,998 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 18 reviews
5.0 (18)
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
,
·
1 bathroom
1 bathroom
29 Aug – 3 Sept
29 Aug – 3 Sept
$4,535 SGD
$3,871 SGD
Show price breakdown
for 5 nights
Free cancellation
4.79 out of 5 average rating, 347 reviews
4.79 (347)
Guest favourite
Guest favourite
Home in Oak Bluffs
Modern cabin in the woods.
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1.5 bathrooms
1.5 bathrooms
1–6 Aug
1–6 Aug
$5,064 SGD
Show price breakdown
for 5 nights
$5,064 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Guest favourite
Guest favourite
Home in Tisbury
Luxurious New Construction in Vineyard Haven
4 bedrooms
4 bedrooms
,
·
1 queen bed
1 queen bed
,
·
4 bathrooms
4 bathrooms
29 Aug – 3 Sept
29 Aug – 3 Sept
$10,509 SGD
Show price breakdown
for 5 nights
$10,509 SGD for 5 nights
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Home in Oak Bluffs
Oak Bluffs retreat with direct pond access
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
3.5 bathrooms
3.5 bathrooms
28 Sept – 3 Oct
28 Sept – 3 Oct
$6,399 SGD
Show price breakdown
for 5 nights
$6,399 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 4 reviews
5.0 (4)
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
$4,798 SGD
Show price breakdown
for 5 nights
$4,798 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 4 reviews
5.0 (4)
1
2
3
4
…
15