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Search results; Over 1,000 homes in Oak Bluffs

Top guest favourite
Cottage in Oak Bluffs
East Chop Cottage - walk to lighthouse & beach!
1 bedroom, 1 bed, 0.5 private bathroom
25–30 Aug
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4.9 out of 5 average rating, 143 reviews
Guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
2 bedrooms, 3 queen beds, 1 bathroom
16–21 Oct
4.93 out of 5 average rating, 309 reviews
Superhost
Place to stay in Oak Bluffs
Oak Bluffs Circuit Av Walk Everywhere Single Room
1 bedroom, 1 bed, 1 bathroom
11–16 Sept
Cabin in Oak Bluffs
Newly built cabin walking distance from Oak Bluffs
1 bedroom, 1 bed, 1 bathroom
21–26 Jul
New place to stay
Top guest favourite
Flat in Oak Bluffs
Town/Beach: Vineyard Vacation Houses welcomes you!
1 bedroom, 2 beds, 1 bathroom
15–20 Oct
4.89 out of 5 average rating, 303 reviews
Guest favourite
Home in Oak Bluffs
Walk to Town, beach and amazing location 113A
2 bedrooms, 2 beds, 1.5 bathrooms
16–21 Aug
4.95 out of 5 average rating, 209 reviews
Top guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
2 bedrooms, 2 double beds, 1 bathroom
31 Aug – 5 Sept
4.95 out of 5 average rating, 424 reviews
Home in Oak Bluffs
OB Salt & Cedar Cottage
4 bedrooms, 9 beds, 2 bathrooms
17–24 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Oak Bluffs
NEW! Charming Oak Bluffs Cottage - Sleeps 8
3 bedrooms, 4 beds, 2 bathrooms
16–21 Jul
New place to stay
Top guest favourite
Home in Oak Bluffs
Pinkletink Plantation
3 bedrooms, 5 beds, 2.5 bathrooms
10–15 Oct
4.98 out of 5 average rating, 51 reviews
Guest favourite
Home in Oak Bluffs
Diamond in The Bluffs - New Home, Private Backyard
2 bedrooms, 2 beds, 1.5 bathrooms
12–17 Jul
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Oak Bluffs
Casa Luca| Serene 3BR| SunRm, Outdr Shwr, A/C, BBQ
3 bedrooms, 5 beds, 1 bathroom
28 Aug – 4 Sept
4.92 out of 5 average rating, 12 reviews
Top guest favourite
Flat in Oak Bluffs
14A Kennebec THE center of OB! No car, No problem!
1 bedroom, 2 beds, 1 bathroom
20–25 Jul
4.97 out of 5 average rating, 29 reviews
Guest favourite
Guest suite in Oak Bluffs
Cottage suite between the harbors: no minimum stay
2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
4.79 out of 5 average rating, 341 reviews
Home in Oak Bluffs
Brand new! MV summer home!
3 bedrooms, 3 beds, 1 bathroom
14–19 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Oak Bluffs
**Vineyard Vacation Retreat** -3 BR
3 bedrooms, 3 beds, 2 bathrooms
8–13 Sept
4.96 out of 5 average rating, 125 reviews
Guest favourite
Home in Oak Bluffs
Oak Bluffs Victorian Walk to Town & Beaches
5 bedrooms, 7 beds, 5.5 bathrooms
18–23 Sept
4.83 out of 5 average rating, 65 reviews
Home in Oak Bluffs
Oak Bluffs Summer Home
3 bedrooms, 4 beds, 2 bathrooms
10–15 Jul
New place to stay
Guest favourite
Home in Oak Bluffs
Studio apt in newly built barn
2 beds, 1 bathroom
27 Sept – 2 Oct
4.94 out of 5 average rating, 511 reviews