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Search results; Over 1,000 homes in Oak Bluffs

Top guest favourite
Room in Oak Bluffs
The Mary Suite- Kathleens Kottage- Oak Bluffs MV
1 bedroom, 1 bed, 1 private bathroom
28 Aug – 2 Sept
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5.0 out of 5 average rating, 35 reviews
Place to stay in Oak Bluffs
A Charming Beach Retreat Just Steps From the Beach
2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
New place to stay
Home in Oak Bluffs
Amanda’s Veranda
4 bedrooms, 5 beds, 3.5 bathrooms
30 Aug – 4 Sept
New place to stay
Home in Oak Bluffs
East Chop Oceanview Escape
6 bedrooms, 8 beds, 4.5 bathrooms
21–27 Aug
5.0 out of 5 average rating, 4 reviews
Home in Oak Bluffs
Adorable Oak Bluffs Gingerbread House
4 bedrooms, 5 beds, 2.5 bathrooms
19–26 Jun
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Oak Bluffs
111D Beautiful clean walk to beach and downtown!
1 bedroom, 2 beds, 1 bathroom
16–21 Aug
4.89 out of 5 average rating, 185 reviews
Top 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, 427 reviews
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, 5 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, 313 reviews
Guest favourite
Home in Oak Bluffs
New Serenity Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Oak Bluffs
113A Walk to Town, beach and amazing location!
2 bedrooms, 2 beds, 1.5 bathrooms
16–21 Aug
4.95 out of 5 average rating, 213 reviews
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, 350 reviews
Top guest favourite
Home in Oak Bluffs
Spectacular beach & pool combo; beautiful sunsets!
4 bedrooms, 5 beds, 5.5 bathrooms
4–9 Oct
4.93 out of 5 average rating, 221 reviews
Home in Oak Bluffs
MV Sea Glenn Flower
4 bedrooms, 6 beds, 3 bathrooms
23–28 Aug
5.0 out of 5 average rating, 4 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, 193 reviews
Top guest favourite
Home in Oak Bluffs
Charming Oak Bluffs Retreat
6 bedrooms, 11 beds, 2.5 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 28 reviews
Guest favourite
Home in Oak Bluffs
Beautiful Home in Oak Bluffs Center!
3 bedrooms, 6 beds, 1 bathroom
16–21 Sept
5.0 out of 5 average rating, 47 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 – 4 Sept
4.94 out of 5 average rating, 16 reviews
Top guest favourite
Home in Tisbury
Sunny, Spacious Vineyard Retreat
3 bedrooms, 5 beds, 2.5 bathrooms
20–25 Sept
4.97 out of 5 average rating, 302 reviews