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Search results; Over 1,000 homes in Oak Bluffs

Guest favourite
Room in Oak Bluffs
Oak Bluffs/ Harbor Views/ Full Bed/ In Town
1 bedroom, 1 bed, 1 private bathroom
29 Aug – 3 Sept
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4.92 out of 5 average rating, 95 reviews
Superhost
Flat in Falmouth
On the Shores of Eel Pond
2 bedrooms, 2 queen beds
22–27 Aug
New place to stay
Home in Oak Bluffs
Amanda’s Veranda
4 bedrooms, 5 beds
30 Aug – 4 Sept
New place to stay
Top guest favourite
Home in Oak Bluffs
113A Walk to Town, beach and amazing location!
2 bedrooms, 2 beds
16–21 Aug
4.95 out of 5 average rating, 213 reviews
Top guest favourite
Home in Oak Bluffs
Spectacular beach & pool combo; beautiful sunsets!
4 bedrooms, 5 beds
4–9 Oct
4.93 out of 5 average rating, 221 reviews
Cabin in Oak Bluffs
Newly built rustic cabin in Oak Bluffs
1 bedroom, 1 bed
30 Aug – 4 Sept
5.0 out of 5 average rating, 4 reviews
Featured hotel
Room in Oak Bluffs
Water view double queen
2 queen beds
16–21 Sept
Top guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
2 bedrooms, 3 queen beds
16–21 Oct
4.93 out of 5 average rating, 313 reviews
Top guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
2 bedrooms, 2 double beds
18–23 Oct
4.95 out of 5 average rating, 427 reviews
Top guest favourite
Flat in Oak Bluffs
14D Kennebec THE center of OB! No car, No problem!
1 bedroom, 2 beds
16–21 Aug
4.94 out of 5 average rating, 32 reviews
Top guest favourite
Home in Tisbury
Martha’s Vineyard Waterfront Private Beach
8 bedrooms, 10 beds
20–25 Sept
5.0 out of 5 average rating, 18 reviews
Guest house in Oak Bluffs
Charming guesthouse in OB
1 bedroom, 2 beds
1–6 Aug
4.88 out of 5 average rating, 8 reviews
Top guest favourite
Flat in Oak Bluffs
111B Beautiful and Short walk beach, town, harbor!
1 bedroom, 2 beds
18–23 Aug
4.93 out of 5 average rating, 87 reviews
Top guest favourite
Home in Oak Bluffs
Casa Luca| Serene 3BR| SunRm, Outdr Shwr, A/C, BBQ
3 bedrooms, 5 beds
28 Aug – 4 Sept
4.93 out of 5 average rating, 15 reviews
Guest favourite
Guest suite in Oak Bluffs
Cottage suite between the harbors: no minimum stay
2 bedrooms, 3 beds
30 Aug – 4 Sept
4.8 out of 5 average rating, 349 reviews
Top guest favourite
Home in Tisbury
Sunny, Spacious Vineyard Retreat
3 bedrooms, 5 beds
20–25 Sept
4.97 out of 5 average rating, 302 reviews
Home in Oak Bluffs
MV Sea Glenn Flower
4 bedrooms, 6 beds
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Flat in Oak Bluffs
Island Oasis
1 bedroom, 3 beds
2–7 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Oak Bluffs
New Serenity Retreat
2 bedrooms, 3 beds
1–6 Aug
5.0 out of 5 average rating, 7 reviews