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Search results; Over 1,000 homes in Oak Bluffs

Guest favourite
Apartment in Oak Bluffs
Serenity on Martha's Vineyard
2 bedrooms, 3 beds, 1 private bathroom
24–29 Sept
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4.83 out of 5 average rating, 53 reviews
Top guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
2 bedrooms, 2 double beds
18–23 Oct
4.95 out of 5 average rating, 424 reviews
Featured hotel
Hotel in Oak Bluffs
Water view double queen
1 bedroom, 2 queen beds
16–21 Sept
Guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
2 bedrooms, 3 queen beds
16–21 Oct
4.93 out of 5 average rating, 309 reviews
Guest favourite
Guest house in Oak Bluffs
Sweet Summer Cottage
1 bedroom, 1 queen bed
26–31 Jul
4.92 out of 5 average rating, 66 reviews
Home in Oak Bluffs
Oak Bluffs Summer Home
3 bedrooms, 4 beds
14–19 Jul
New place to stay
Guest favourite
Cottage in Oak Bluffs
Oak Bluffs, Martha's Vineyard; Gingerbread House
3 bedrooms, 4 beds
17–24 Jul
4.88 out of 5 average rating, 16 reviews
Guest favourite
Home in Oak Bluffs
Studio apt in newly built barn
2 beds
27 Sept – 2 Oct
4.94 out of 5 average rating, 512 reviews
Superhost
Home in Oak Bluffs
Quintessential 1920s renovated bungalow new 2026!
2 bedrooms, 2 beds
23–28 Jul
New place to stay
Guest favourite
Cottage in Oak Bluffs
Beautiful clean walk to Town, Inkwell and harbor!
1 bedroom, 2 beds
22–27 Jul
4.95 out of 5 average rating, 189 reviews
Top guest favourite
Guest house in Oak Bluffs
Oak bluffs cottage Perfect place to honeymoon!
2 bedrooms, 2 beds
1–6 Sept
4.97 out of 5 average rating, 133 reviews
Top guest favourite
Flat in Oak Bluffs
Beautiful private apartment walk to everything!
1 bedroom, 2 beds
21–26 Jul
4.95 out of 5 average rating, 194 reviews
Top guest favourite
Flat in Oak Bluffs
14A Kennebec THE center of OB! No car, No problem!
1 bedroom, 2 beds
20–25 Jul
4.97 out of 5 average rating, 29 reviews
Superhost
Place to stay in Oak Bluffs
Oak Bluffs Circuit Av Walk Everywhere Single Room
1 bedroom, 7 beds
11–16 Sept
Top guest favourite
Room in Oak Bluffs
Ocean Park Victorian
1 double bed
13–18 Sept
4.99 out of 5 average rating, 221 reviews
Top guest favourite
Home in Oak Bluffs
The Oak Bluffs House - Walk to Beach & Town
2 bedrooms, 3 beds
14–19 Jul
5.0 out of 5 average rating, 140 reviews
Guest favourite
Room in Oak Bluffs
Oak Bluffs/ Harbor Views/ Queen Bed/ In Town
1 queen bed
30 Aug – 4 Sept
4.91 out of 5 average rating, 107 reviews
Top guest favourite
Flat in Oak Bluffs
Cozy 3 bedroom apartment with King bed on Main St.
3 bedrooms, 5 beds
11–16 Oct
4.96 out of 5 average rating, 97 reviews
Home in Edgartown
Vineyard Family Home
3 bedrooms, 3 beds
27 Aug – 1 Sept