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Search results; Over 1,000 homes in Oak Bluffs

Guest favourite
Home in Oak Bluffs
impeccable cottage STEPS to downtown OB & beach!
3 bedrooms, 6 beds, 1 private bathroom
20–25 Sept
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4.92 out of 5 average rating, 208 reviews
Featured hotel
Hotel in Oak Bluffs
Water view double queen
1 bedroom, 1 bathroom
16–21 Sept
Top guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
4.95 out of 5 average rating, 423 reviews, 2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
Guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
4.93 out of 5 average rating, 308 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Oct
Cabin in Oak Bluffs
Newly built cabin walking distance from Oak Bluffs
New place to stay, 1 bedroom, 1 bed, 1 bathroom
21–26 Jul
Guest favourite
Guest house in Oak Bluffs
Sweet Summer Cottage
4.92 out of 5 average rating, 65 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Jul
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
12–19 Jul
Top guest favourite
Guest house in Oak Bluffs
Oak bluffs cottage Perfect place to honeymoon!
4.97 out of 5 average rating, 132 reviews, 2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
Guest favourite
Home in Oak Bluffs
Studio apt in newly built barn
4.94 out of 5 average rating, 511 reviews, 2 beds, 1 bathroom
27 Sept – 2 Oct
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
Guest favourite
Room in Oak Bluffs
Oak Bluffs/ Harbor Views/ Queen Bed/ In Town
4.9 out of 5 average rating, 104 reviews, 1 queen bed, 1 bathroom
30 Aug – 4 Sept
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
Diamond in The Bluffs - New Home, Private Backyard
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
11–16 Jul
Top guest favourite
Flat in Oak Bluffs
Beautiful private apartment walk to everything!
4.95 out of 5 average rating, 194 reviews, 1 bedroom, 2 beds, 1 bathroom
18–23 Jul
Top guest favourite
Guest suite in Oak Bluffs
Quiet Hide Away
4.98 out of 5 average rating, 196 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
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
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
Top guest favourite
Flat in Oak Bluffs
Town/Beach: Vineyard Vacation Houses welcomes you!
4.89 out of 5 average rating, 303 reviews, 1 bedroom, 2 beds, 1 bathroom
15–20 Oct
Home in Oak Bluffs
Brand new! MV summer home!
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 3 beds, 1 bathroom
14–19 Jul