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Search results; Over 1,000 homes in Oak Bluffs

Top guest favourite
Guest house in Oak Bluffs
Mermaid Cottage
1 bedroom, 1 bed, 1 private bathroom
24–31 Jan
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4.99 out of 5 average rating, 101 reviews
Place to stay in Oak Bluffs
A Charming Beach Retreat Just Steps From the Beach
New place to stay, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
Home in Oak Bluffs
Amanda’s Veranda
New place to stay, 4 bedrooms, 5 beds, 3.5 bathrooms
30 Aug – 4 Sept
Home in Oak Bluffs
East Chop Oceanview Escape
5.0 out of 5 average rating, 4 reviews, 6 bedrooms, 8 beds, 4.5 bathrooms
21–27 Aug
Home in Oak Bluffs
Adorable Oak Bluffs Gingerbread House
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
19–26 Jun
Top guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
4.95 out of 5 average rating, 427 reviews, 2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
Cabin in Oak Bluffs
Newly built rustic cabin in Oak Bluffs
5.0 out of 5 average rating, 4 reviews, 1 bedroom, 1 bed, 1 bathroom
13–18 Sept
Top guest favourite
Cottage in Oak Bluffs
111I Beautiful and walk to everything Oak Bluffs!
4.97 out of 5 average rating, 183 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
13–18 Sept
Top guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
4.93 out of 5 average rating, 313 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Oct
Guest favourite
Home in Oak Bluffs
New Serenity Retreat
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
29 Aug – 3 Sept
Guest favourite
Home in Oak Bluffs
Brand new! MV summer home!
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 3 beds, 1 bathroom
26–31 Aug
Guest favourite
Guest suite in Oak Bluffs
Cottage suite between the harbors: no minimum stay
4.8 out of 5 average rating, 350 reviews, 2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
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
Home in Oak Bluffs
Spectacular beach & pool combo; beautiful sunsets!
4.93 out of 5 average rating, 221 reviews, 4 bedrooms, 5 beds, 5.5 bathrooms
4–9 Oct
Home in Oak Bluffs
MV Sea Glenn Flower
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 6 beds, 3 bathrooms
23–28 Aug
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
Top guest favourite
Home in Oak Bluffs
Charming Oak Bluffs Retreat
4.96 out of 5 average rating, 28 reviews, 6 bedrooms, 11 beds, 2.5 bathrooms
27 Sept – 2 Oct
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
28 Aug – 4 Sept
Home in Oak Bluffs
Charming 3BR Cottage Near the Beach w/ Deck
3 bedrooms, 4 beds, 1 bathroom
30 Aug – 4 Sept