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Search results; Over 1,000 homes in Oak Bluffs

Top guest favourite
Guest suite in Oak Bluffs
Quiet Hide Away
1 bedroom, 1 bed, 1 private bathroom
22–27 Aug
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4.98 out of 5 average rating, 202 reviews
Top guest favourite
Cabin in Oak Bluffs
Newly built rustic cabin in Oak Bluffs
1 bedroom, 1 bed, 1 bathroom
13–18 Sept
4.92 out of 5 average rating, 12 reviews
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, 432 reviews
Guest favourite
Home in Oak Bluffs
Studio apt in newly built barn
2 beds, 1 bathroom
28 Sept – 3 Oct
4.94 out of 5 average rating, 519 reviews
Top guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
2 bedrooms, 3 queen beds, 1 bathroom
19–24 Oct
4.93 out of 5 average rating, 316 reviews
Featured hotel
Room in Oak Bluffs
Water view double queen
2 queen beds, 1 bathroom
20–25 Sept
Top guest favourite
Room in Tisbury
Vineyard Haven Sanctuary- free bikes!
1 queen bed, 1 bathroom
20–25 Sept
4.94 out of 5 average rating, 139 reviews
Superhost
Room in Oak Bluffs
Oak Bluffs Circuit Av Walk Everywhere Single Room
1 double bed, 1 bathroom
13–18 Sept
Guest favourite
Flat in Oak Bluffs
14A Kennebec THE center of OB! No car, No problem!
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
4.97 out of 5 average rating, 34 reviews
Top guest favourite
Home in Oak Bluffs
113A Walk to Town, beach and amazing location!
2 bedrooms, 2 beds, 1.5 bathrooms
7–12 Sept
4.95 out of 5 average rating, 217 reviews
Guest house in Oak Bluffs
Charming guesthouse in OB
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.91 out of 5 average rating, 11 reviews
Top guest favourite
Flat in Oak Bluffs
111C Beautiful private condo walk to everything!
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.95 out of 5 average rating, 201 reviews
Home in Oak Bluffs
Waterfront Retreat w/ Guest Cottage & Sunsets
4 bedrooms, 5 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 3 reviews
Guest favourite
Cottage in Oak Bluffs
111H Beautiful clean walk to Town, Inkwell, harbor
1 bedroom, 2 beds, 1.5 bathrooms
13–18 Sept
4.95 out of 5 average rating, 199 reviews
Home in Oak Bluffs
Amanda’s Veranda
4 bedrooms, 5 beds, 3.5 bathrooms
27 Sept – 2 Oct
New place to stay
Top guest favourite
Cottage in Tisbury
Not Your Great Aunt's Island Cottage
3 bedrooms, 5 beds, 1 bathroom
17–22 Oct
4.96 out of 5 average rating, 313 reviews
Top guest favourite
Rooms in Edgartown
The Alison Boylston Piazza House
2 bedrooms, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.85 out of 5 average rating, 563 reviews
Top guest favourite
Home in Oak Bluffs
Pinkletink Plantation
3 bedrooms, 5 beds, 2.5 bathrooms
16–21 Oct
4.98 out of 5 average rating, 58 reviews
Guest favourite
Room in Oak Bluffs
Oak Bluffs/ Harbor Views/ Queen Bed/ In Town
1 queen bed, 1 bathroom
24–29 Aug
4.92 out of 5 average rating, 118 reviews