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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, 2 private bathrooms
24–29 Sept
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4.83 out of 5 average rating, 53 reviews
Featured hotel
Hotel in Oak Bluffs
Water view double queen
1 bedroom, 2 queen beds, 1 bathroom
16–21 Sept
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
Top guest favourite
Guest house in Oak Bluffs
Oak bluffs cottage Perfect place to honeymoon!
2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
4.97 out of 5 average rating, 132 reviews
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
Guest favourite
Cottage in Oak Bluffs
Oak Bluffs, Martha's Vineyard; Gingerbread House
3 bedrooms, 4 beds, 1.5 bathrooms
13–20 Jul
4.88 out of 5 average rating, 16 reviews
Superhost
Home in Oak Bluffs
Quintessential 1920s renovated bungalow new 2026!
2 bedrooms, 2 beds, 1.5 bathrooms
23–28 Jul
New place to stay
Guest favourite
Guest house in Oak Bluffs
Sweet Summer Cottage
1 bedroom, 1 queen bed, 1 bathroom
26–31 Jul
4.92 out of 5 average rating, 65 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
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
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
Room in Oak Bluffs
Oak Bluffs/ Harbor Views/ Queen Bed/ In Town
1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.9 out of 5 average rating, 104 reviews
Top guest favourite
Flat in Oak Bluffs
Beautiful private apartment walk to everything!
1 bedroom, 2 beds, 1 bathroom
18–23 Jul
4.95 out of 5 average rating, 194 reviews
Home in Oak Bluffs
Oak Bluffs Summer Home
3 bedrooms, 4 beds, 2 bathrooms
10–15 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
Oak Bluffs | A/C, Outdoor Shower, Walk to Town
3 bedrooms, 6 beds, 1 bathroom
11–16 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Oak Bluffs
** Vineyard Vacation Retreat ** with HOT TUB
2 bedrooms, 2 beds, 2.5 bathrooms
19–24 Sept
4.92 out of 5 average rating, 144 reviews
Guest favourite
Cottage in Oak Bluffs
In town Cozy-Cottage-Glam w/ Fab backyard 2bd/2B
2 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
4.95 out of 5 average rating, 22 reviews
Home in Edgartown
Vineyard Family Home
3 bedrooms, 3 beds, 1 bathroom
18–23 Jul