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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, 210 reviews
Guest favourite
Flat in Oak Bluffs
Single Occupancy Oak Bluffs Studio Apartment
4.96 out of 5 average rating, 28 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Aug
Featured hotel
Hotel in Oak Bluffs
Partial water view queen
4.8 out of 5 average rating, 5 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
4.95 out of 5 average rating, 426 reviews, 2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
Cabin in Oak Bluffs
Newly built rustic cabin in Oak Bluffs
5.0 out of 5 average rating, 4 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
Superhost
Room in Oak Bluffs
Oak Bluffs Circuit Av Walk Everywhere Single Room
1 double bed, 1 bathroom
11–16 Sept
Guest favourite
Flat in Oak Bluffs
Town/Beach: Vineyard Vacation Houses welcomes you!
4.89 out of 5 average rating, 304 reviews, 1 bedroom, 2 beds, 1 bathroom
15–20 Oct
Top guest favourite
Room in Tisbury
Vineyard Haven Sanctuary- free bikes!
4.94 out of 5 average rating, 139 reviews, 1 queen bed, 1 bathroom
13–18 Sept
Top guest favourite
Cottage in Oak Bluffs
111I Beautiful and walk to everything Oak Bluffs!
4.97 out of 5 average rating, 183 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
13–18 Sept
Superhost
Room in Tisbury
Lovely Room in Vineyard Haven
4.82 out of 5 average rating, 121 reviews, 1 double bed, 1 bathroom
23–28 Aug
Guest favourite
Home in Oak Bluffs
Beautiful Oak Bluffs Cottage Close to Town
4.98 out of 5 average rating, 44 reviews, 3 bedrooms, 4 beds, 2 bathrooms
6–11 Oct
Guest favourite
Home in Oak Bluffs
Studio apt in newly built barn
4.94 out of 5 average rating, 516 reviews, 2 beds, 1 bathroom
27 Sept – 2 Oct
Guest favourite
Tiny home in Oak Bluffs
Delightful 1BR House near all! Walk to beach.
5.0 out of 5 average rating, 9 reviews, 1 bedroom, 2 beds, 1 bathroom
1–6 Aug
Top guest favourite
Flat in Oak Bluffs
Cozy 3 bedroom apartment with King bed on Main St.
4.96 out of 5 average rating, 98 reviews, 3 bedrooms, 5 beds, 1 bathroom
11–16 Oct
Top guest favourite
Guest house in Tisbury
Island Home. Secluded guest house in spacious yard
4.97 out of 5 average rating, 96 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
Home in Oak Bluffs
Charming Cottage on Harbor on Martha's Vineyard
5.0 out of 5 average rating, 5 reviews, 4 bedrooms, 5 beds, 2 bathrooms
3–10 Oct
Superhost
Flat in Oak Bluffs
Pet-Friendly Oak Bluffs 3BR | Deck & Fire Pit
4.81 out of 5 average rating, 21 reviews, 4 bedrooms, 5 beds, 1 bathroom
2–7 Aug
Top guest favourite
Room in Oak Bluffs
Ocean Park Victorian
4.99 out of 5 average rating, 225 reviews, 1 double bed, 1 bathroom
22–27 Nov
Guest favourite
Guest house in Oak Bluffs
Sweet Summer Cottage
4.93 out of 5 average rating, 67 reviews, 1 bedroom, 1 bed, 1 bathroom
7–12 Sept