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Search results; Over 1,000 homes in Oak Bluffs

Guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
2 bedrooms, 3 beds, 1 private bathroom
16–21 Oct
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4.93 out of 5 average rating, 309 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
Guest favourite
Cottage in Oak Bluffs
Beautiful walk to Town, Inkwell and harbor!
4.95 out of 5 average rating, 218 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
27 Jul – 1 Aug
Guest favourite
Cottage in Oak Bluffs
Oak Bluffs, Martha's Vineyard; Gingerbread House
4.88 out of 5 average rating, 16 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
16–23 Jul
Home in Oak Bluffs
Oak Bluffs Summer Home
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
13–18 Jul
Featured hotel
Hotel in Oak Bluffs
King
5.0 out of 5 average rating, 6 reviews, 1 bedroom, 1 bed, 1 bathroom
20–25 Sept
Guest suite in Tisbury
Serene Garden Experience
New place to stay, 1 bedroom, 1 bed, 2 bathrooms
14–19 Jul
Top guest favourite
Flat in Oak Bluffs
14A Kennebec THE center of OB! No car, No problem!
4.97 out of 5 average rating, 29 reviews, 1 bedroom, 2 beds, 1 bathroom
20–25 Jul
Guest favourite
Home in Oak Bluffs
Studio apt in newly built barn
4.94 out of 5 average rating, 512 reviews, 2 beds, 1 bathroom
27 Sept – 2 Oct
Guest favourite
Home in Oak Bluffs
Diamond in The Bluffs - New Home, Private Backyard
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
15–20 Jul
Top guest favourite
Guest house in Oak Bluffs
Oak bluffs cottage Perfect place to honeymoon!
4.97 out of 5 average rating, 133 reviews, 2 bedrooms, 2 beds, 1 bathroom
25–30 Jul
Guest favourite
Cottage in Oak Bluffs
Beautiful clean walk to Town, Inkwell and harbor!
4.95 out of 5 average rating, 189 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
22–27 Jul
Guest favourite
Guest house in Oak Bluffs
Sweet Summer Cottage
4.92 out of 5 average rating, 66 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Jul
Superhost
Home in Oak Bluffs
Quintessential 1920s renovated bungalow new 2026!
New place to stay, 2 bedrooms, 2 beds, 1.5 bathrooms
23–28 Jul
Top guest favourite
Home in Oak Bluffs
The Oak Bluffs House - Walk to Beach & Town
5.0 out of 5 average rating, 140 reviews, 2 bedrooms, 3 beds, 2.5 bathrooms
13–18 Jul
Superhost
Place to stay in Oak Bluffs
Oak Bluffs Circuit Av Walk Everywhere Single Room
1 bedroom, 7 beds, 1 bathroom
11–16 Sept
Guest favourite
Room in Oak Bluffs
Oak Bluffs/ Harbor Views/ Queen Bed/ In Town
4.91 out of 5 average rating, 107 reviews, 1 queen bed, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Cottage in Oak Bluffs
In town Cozy-Cottage-Glam w/ Fab backyard 2bd/2B
4.95 out of 5 average rating, 22 reviews, 2 bedrooms, 3 beds, 2 bathrooms
28 Aug – 2 Sept
Top guest favourite
Room in Tisbury
Vineyard Haven Sanctuary- free bikes!
4.94 out of 5 average rating, 138 reviews, 1 queen bed, 1 bathroom
13–18 Sept