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Search results; Over 1,000 homes in Oak Bluffs

Descriptions are based on details hosts provide
Guest favourite
Apartment in Oak Bluffs
LOCATION LOCATION!! Ocean- View TOP Floor Condo
2 bedrooms, 3 beds, 2 private bathrooms
23–28 Sept
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4.97 out of 5 average rating, 35 reviews
Top guest favourite
Guest suite in Oak Bluffs
Right on the bike path, private entrance
2 bedrooms, 2 double beds, 1 bathroom
18–23 Oct
4.95 out of 5 average rating, 424 reviews
Featured hotel
Hotel in Oak Bluffs
King
1 bedroom, 1 king bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 6 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
Home in Oak Bluffs
Peaceful home near the Lagoon
3 bedrooms, 4 beds, 2 bathrooms
15–20 Jul
New place to stay
Guest favourite
Cottage in Oak Bluffs
Oak Bluffs, Martha's Vineyard; Gingerbread House
3 bedrooms, 4 beds, 1.5 bathrooms
17–24 Jul
4.88 out of 5 average rating, 16 reviews
Top guest favourite
Room in Tisbury
Harbor views, 2 blocks from the ferry
1 queen bed, 1 bathroom
13–18 Sept
4.94 out of 5 average rating, 138 reviews
Top guest favourite
Guest house in Oak Bluffs
Enclosed hot tub, half mile from beaches
2 bedrooms, 2 beds, 1 bathroom
1–6 Sept
4.97 out of 5 average rating, 133 reviews
Guest favourite
Guest house in Oak Bluffs
Walk to Inkwell Beach and Circuit Ave
1 bedroom, 1 queen bed, 1 bathroom
26–31 Jul
4.92 out of 5 average rating, 66 reviews
Top guest favourite
Flat in Oak Bluffs
Renovated 1800s home in the heart of town
1 bedroom, 2 beds, 1 bathroom
15–20 Oct
4.89 out of 5 average rating, 303 reviews
Guest favourite
Home in Oak Bluffs
Post-and-beam barn near the beach
2 beds, 1 bathroom
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, 1.5 bathrooms
23–28 Jul
New place to stay
Superhost
Place to stay in Oak Bluffs
Oak Bluffs Circuit Av Walk Everywhere Single Room
1 bedroom, 7 beds, 1 bathroom
11–16 Sept
Home in Edgartown
Vineyard Family Home
3 bedrooms, 3 beds, 1 bathroom
27 Aug – 1 Sept
Top guest favourite
Guest suite in Oak Bluffs
3-minute walk to the beach
1 bedroom, 2 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 39 reviews
Guest favourite
Home in Oak Bluffs
Diamond in The Bluffs - New Home, Private Backyard
2 bedrooms, 2 beds, 1.5 bathrooms
18–23 Jul
5.0 out of 5 average rating, 9 reviews
Guest favourite
Room in Oak Bluffs
Harbor views from a Victorian home
1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.91 out of 5 average rating, 108 reviews
Top guest favourite
Cottage in Tisbury
Vaulted ceilings and a wrap-around deck
1 bedroom, 1 queen bed, 1 bathroom
19–24 Sept
4.97 out of 5 average rating, 77 reviews
Guest favourite
Cottage in Oak Bluffs
Beautiful clean walk to Town, Inkwell and harbor!
1 bedroom, 2 beds, 1.5 bathrooms
22–27 Jul
4.95 out of 5 average rating, 189 reviews