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Search results; Over 1,000 homes in Oak Bluffs

Guest favourite
Boutique hotel in Oak Bluffs
Balcony Room at the Tivoli Inn
1 bedroom, 2 beds, 1 private bathroom
30 Aug – 4 Sept
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4.91 out of 5 average rating, 54 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
22–27 Aug
Featured hotel
Hotel in Oak Bluffs
Partial water view queen
4.75 out of 5 average rating, 4 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
Guest favourite
Guest house in Oak Bluffs
Sweet Summer Cottage
4.92 out of 5 average rating, 66 reviews, 1 bedroom, 1 bed, 1 bathroom
7–12 Sept
Cabin in Oak Bluffs
Newly built rustic cabin in Oak Bluffs
New place to stay, 1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Cottage in Oak Bluffs
111H Beautiful clean walk to Town, Inkwell, harbor
4.95 out of 5 average rating, 193 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
13–18 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
Room in Oak Bluffs
Oak Bluffs Circuit Av Walk Everywhere Single Room
1 double bed, 1 bathroom
11–16 Sept
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
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
Guest favourite
Home in Oak Bluffs
Newly rebuilt house! Walk to town and beaches!
5.0 out of 5 average rating, 7 reviews, 4 bedrooms, 4 beds, 3.5 bathrooms
1–6 Dec
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
Flat in Oak Bluffs
Town/Beach: Vineyard Vacation Houses welcomes you!
4.89 out of 5 average rating, 303 reviews, 1 bedroom, 2 beds, 1 bathroom
15–20 Oct
Guest favourite
Cottage in Oak Bluffs
111E Beautiful stroll to beach and all downtown!
4.89 out of 5 average rating, 212 reviews, 1 bedroom, 2 beds, 1 bathroom
16–21 Oct
Guest favourite
Home in Oak Bluffs
Studio apt in newly built barn
4.94 out of 5 average rating, 514 reviews, 2 beds, 1 bathroom
27 Sept – 2 Oct
Guest favourite
Rooms in Oak Bluffs
Entire 3- bedroom upstairs of Vineyard home
4.86 out of 5 average rating, 37 reviews, 3 bedrooms, 3 beds, 1 bathroom
1–6 Apr
Top guest favourite
Flat in Oak Bluffs
Cozy 3 bedroom apartment with King bed on Main St.
4.96 out of 5 average rating, 97 reviews, 3 bedrooms, 5 beds, 1 bathroom
11–16 Oct
Guest suite in Oak Bluffs
NEW Luxe suite|outdoor shower|firepit|walk to town
1 bedroom, 2 beds, 1 bathroom
22–29 Aug