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Search results; Over 1,000 homes in Oak Bluffs

Top guest favourite
Home in Oak Bluffs
NEW Modern Open Floor Plan House in Heart of OB
3 bedrooms, 4 beds, 4 private bathrooms
7–13 Sept
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5.0 out of 5 average rating, 44 reviews
Top guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
4.95 out of 5 average rating, 424 reviews, 2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
Top guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
4.93 out of 5 average rating, 309 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Oct
Home in Oak Bluffs
OB Salt & Cedar Cottage
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 9 beds, 2 bathrooms
24–31 Aug
Top guest favourite
Home in Oak Bluffs
Pinkletink Plantation
4.98 out of 5 average rating, 52 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
10–15 Oct
Guest favourite
Home in Oak Bluffs
Oak Bluffs Victorian Walk to Town & Beaches
4.83 out of 5 average rating, 65 reviews, 5 bedrooms, 7 beds, 5.5 bathrooms
29 Sept – 4 Oct
Guest favourite
Home in Oak Bluffs
Walk to Town, beach and amazing location 113A
4.95 out of 5 average rating, 209 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
16–21 Aug
Cabin in Oak Bluffs
Newly built rustic cabin in Oak Bluffs
New place to stay, 1 bedroom, 1 bed, 1 bathroom
21–26 Jul
Top guest favourite
Cottage in Oak Bluffs
The WestLake
5.0 out of 5 average rating, 10 reviews, 4 bedrooms, 5 beds, 2 bathrooms
26 Sept – 1 Oct
Superhost
Place to stay in Oak Bluffs
Oak Bluffs Circuit Av Walk Everywhere Single Room
1 bedroom, 7 beds, 1 bathroom
11–16 Sept
Top guest favourite
Home in Tisbury
Sunny, Spacious Vineyard Retreat
4.97 out of 5 average rating, 301 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
13–18 Sept
Superhost
Home in Oak Bluffs
NEW! Charming Oak Bluffs Cottage - Sleeps 8
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
16–21 Jul
Top guest favourite
Home in Oak Bluffs
Charming Oak Bluffs Retreat
4.96 out of 5 average rating, 26 reviews, 6 bedrooms, 11 beds, 2.5 bathrooms
27 Sept – 2 Oct
Top guest favourite
Home in Oak Bluffs
Updated cottage/ ocean views
5.0 out of 5 average rating, 20 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
27 Sept – 2 Oct
Home in Oak Bluffs
The East Chop Hideaway-walking distance everywhere
New place to stay, 4 bedrooms, 6 beds, 2 bathrooms
28 Aug – 2 Sept
Top guest favourite
Home in Oak Bluffs
** Vineyard Vacation Retreat ** with HOT TUB
4.92 out of 5 average rating, 144 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
19–24 Sept
Top guest favourite
Home in Oak Bluffs
1/2 mile walk to Downtown Oak Bluffs
4.97 out of 5 average rating, 30 reviews, 3 bedrooms, 7 beds, 2 bathrooms
4–9 Oct
Guest favourite
Guest suite in Oak Bluffs
Cottage suite between the harbors: no minimum stay
4.79 out of 5 average rating, 343 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Top guest favourite
Room in Oak Bluffs
Ocean Park Victorian
4.99 out of 5 average rating, 221 reviews, 1 double bed, 1 bathroom
13–18 Sept