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Search results; Over 1,000 homes in Oak Bluffs

Nature lodge in Oak Bluffs
Lovely King-sized guest room in beautiful home
1 bedroom, 1 bed, 1 shared bathroom
10–15 Jul
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4.88 out of 5 average rating, 18 reviews
Featured hotel
Hotel in Oak Bluffs
Water view double queen
1 bedroom, 2 queen beds, 1 bathroom
16–21 Sept
Top guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
2 bedrooms, 2 double beds, 1 bathroom
18–23 Oct
4.95 out of 5 average rating, 423 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
The Luxury Vineyard Yurt
2 bedrooms, 3 queen beds, 1 bathroom
16–21 Oct
4.93 out of 5 average rating, 309 reviews
Guest favourite
Cottage in Oak Bluffs
Oak Bluffs, Martha's Vineyard; Gingerbread House
3 bedrooms, 4 beds, 1.5 bathrooms
12–19 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
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
Home in Oak Bluffs
Diamond in The Bluffs - New Home, Private Backyard
2 bedrooms, 2 beds, 1.5 bathrooms
11–16 Jul
5.0 out of 5 average rating, 9 reviews
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
Guest favourite
Home in Oak Bluffs
Oak Bluffs | A/C, Outdoor Shower, Walk to Town
3 bedrooms, 6 beds, 1 bathroom
10–15 Jul
5.0 out of 5 average rating, 7 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
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
Top guest favourite
Room in Tisbury
Historic Captain's House. Walk to town and ferry
2 beds, 1 bathroom
29 Sept – 4 Oct
4.99 out of 5 average rating, 154 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
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
Apartment in Oak Bluffs
FABULOUS OCEAN VIEWS-Oak Bluffs Condo Across Beach
2 bedrooms, 3 beds, 2 bathrooms
26 Jul – 1 Aug
5.0 out of 5 average rating, 31 reviews
Home in Edgartown
Vineyard Family Home
3 bedrooms, 3 beds, 1 bathroom
27 Aug – 1 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