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Search results; Over 1,000 homes in Oak Bluffs

Descriptions are based on details hosts provide
Guest favourite
Home in Oak Bluffs
Vineyard Vacation, 3-Bedroom, Hot-tub, Golf course
3 bedrooms, 3 beds, 2 private bathrooms
23–28 Aug
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4.95 out of 5 average rating, 38 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
Oak Bluffs Summer Home
3 bedrooms, 4 beds, 2 bathrooms
15–20 Jul
New place to stay
Guest favourite
Cottage in Oak Bluffs
1871 gingerbread cottage with harbor views
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
Vineyard Haven Sanctuary- free bikes!
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
Oak bluffs cottage Perfect place to honeymoon!
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
Sweet Summer Cottage
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
Superhost
Home in Oak Bluffs
Renovated 1920s bungalow near downtown
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, 512 reviews
Home in Edgartown
Vineyard Family Home
3 bedrooms, 3 beds, 1 bathroom
27 Aug – 1 Sept
Superhost
Place to stay in Oak Bluffs
Private entrance, walk to the beach
1 bedroom, 7 beds, 1 bathroom
11–16 Sept
Top guest favourite
Guest suite in Oak Bluffs
Spacious 1 Bedroom Apt - 3 min walk to the Beach!
1 bedroom, 2 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 39 reviews
Guest favourite
Room in Oak Bluffs
Oak Bluffs/ Harbor Views/ Queen Bed/ In Town
1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.91 out of 5 average rating, 108 reviews
Guest favourite
Home in Oak Bluffs
New-build home with a fire pit
2 bedrooms, 2 beds, 1.5 bathrooms
18–23 Jul
5.0 out of 5 average rating, 9 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
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