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Search results; Over 1,000 homes in Oak Bluffs

Top guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
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4.95 out of 5 average rating, 426 reviews
Top guest favourite
Flat in Oak Bluffs
111C Beautiful private condo walk to everything!
4.95 out of 5 average rating, 195 reviews, 1 bedroom, 2 beds, 1 bathroom
16–21 Aug
Guest favourite
Guest suite in Oak Bluffs
Cottage suite between the harbors: no minimum stay
4.79 out of 5 average rating, 347 reviews, 2 bedrooms, 3 beds, 1 bathroom
29 Aug – 3 Sept
Home in Oak Bluffs
Oak Bluffs Oasis. Walk to town, beach & ferry.
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 3 beds, 1 bathroom
22–28 Aug
Guest favourite
Cottage in Oak Bluffs
111H Beautiful clean walk to Town, Inkwell, harbor
4.95 out of 5 average rating, 192 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
30 Aug – 4 Sept
Top guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
4.93 out of 5 average rating, 312 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Oct
Top guest favourite
Home in Oak Bluffs
113A Walk to Town, beach and amazing location!
4.95 out of 5 average rating, 213 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
16–21 Aug
Top guest favourite
Flat in Oak Bluffs
14A Kennebec THE center of OB! No car, No problem!
4.97 out of 5 average rating, 32 reviews, 1 bedroom, 2 beds, 1 bathroom
17–22 Aug
Featured hotel
Room in Oak Bluffs
Queen suite double queen
1 bathroom
24–29 Aug
Home in Oak Bluffs
MV Sea Glenn Flower
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 6 beds, 3 bathrooms
23–28 Aug
Top guest favourite
Home in Oak Bluffs
Casa Luca| Serene 3BR| SunRm, Outdr Shwr, A/C, BBQ
4.93 out of 5 average rating, 15 reviews, 3 bedrooms, 5 beds, 1 bathroom
2–7 Aug
Top guest favourite
Home in Oak Bluffs
Pinkletink Plantation
4.98 out of 5 average rating, 53 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
10–15 Oct
Guest favourite
Home in Oak Bluffs
Modern cabin in the woods.
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
1–6 Aug
Flat in Tisbury
Vineyard Sweet Escape
New place to stay, 1 bedroom, 2 beds, 1 bathroom
20–25 Aug
Home in Oak Bluffs
OB Salt & Cedar Cottage
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 9 beds, 2 bathrooms
24–31 Aug
Home in Oak Bluffs
Welcome to your Oak Bluffs Oasis
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
24–29 Aug
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
Flat in Oak Bluffs
Island Oasis
5.0 out of 5 average rating, 4 reviews, 1 bedroom, 3 beds, 1 bathroom
2–7 Aug
Superhost
Home in Oak Bluffs
Hidden home in the North Bluff
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 3 beds, 3 bathrooms
23–28 Aug