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Search results; Over 1,000 homes in Oak Bluffs

Guest favourite
Apartment in Oak Bluffs
113B Cutest! Walk to Beach, Town and Harbor!
1 bedroom, 1 bed, 1 private bathroom
19–24 Aug
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4.9 out of 5 average rating, 269 reviews
Guest favourite
Cabin in Oak Bluffs
Newly built rustic cabin in Oak Bluffs
1 bedroom, 1 bed, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 8 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, 428 reviews
Flat in Oak Bluffs
The Blue Hydrangea | Your Private Island Retreat
1 bedroom, 1 queen bed, 1 bathroom
21–26 Aug
New place to stay
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
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, 518 reviews
Featured hotel
Room in Oak Bluffs
Water view double queen
2 queen beds, 1 bathroom
12–17 Sept
Top guest favourite
Guest suite in Oak Bluffs
Cottage suite between the harbors: no minimum stay
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.8 out of 5 average rating, 351 reviews
Superhost
Room in Oak Bluffs
Oak Bluffs Circuit Av Walk Everywhere Single Room
1 double bed, 1 bathroom
13–18 Sept
Home in Oak Bluffs
Amanda’s Veranda
4 bedrooms, 5 beds, 3.5 bathrooms
30 Aug – 4 Sept
New place to stay
Top guest favourite
Guest suite in Oak Bluffs
Quiet Hide Away
1 bedroom, 1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 200 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, 115 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, 194 reviews
Guest favourite
Home in Tisbury
Vineyard Haven Walk to Ferry
3 bedrooms, 5 beds, 2 bathrooms
18–23 Oct
4.93 out of 5 average rating, 187 reviews
Top guest favourite
Home in Oak Bluffs
Casa Luca| Serene 3BR| SunRm, Outdr Shwr, A/C, BBQ
3 bedrooms, 5 beds, 1 bathroom
28 Aug – 2 Sept
4.94 out of 5 average rating, 17 reviews
Guest favourite
Home in Oak Bluffs
Modern cabin in the woods.
3 bedrooms, 4 beds, 1.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Room in Oak Bluffs
Ocean Park Victorian
1 double bed, 1 bathroom
22–27 Nov
4.99 out of 5 average rating, 226 reviews
Home in Oak Bluffs
Oak Bluffs Summer Home
3 bedrooms, 4 beds, 2 bathrooms
5–10 Sept
New place to stay
Guest house in Oak Bluffs
Charming guesthouse in OB
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
4.89 out of 5 average rating, 9 reviews