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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, 268 reviews
Home in Oak Bluffs
Amanda’s Veranda
4 bedrooms, 5 beds
30 Aug – 4 Sept
New place to stay
Top guest favourite
Cottage in Oak Bluffs
The WestLake
4 bedrooms, 5 beds
3–8 Oct
5.0 out of 5 average rating, 12 reviews
Home in Oak Bluffs
Newly restored cottage in downtown Oak Bluffs!
3 bedrooms, 7 beds
13–18 Sept
New place to stay
Top guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
2 bedrooms, 3 queen beds
19–24 Oct
4.93 out of 5 average rating, 314 reviews
Home in Oak Bluffs
Oak Bluffs Summer Home
3 bedrooms, 4 beds
5–10 Sept
New place to stay
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
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
Top guest favourite
Home in Oak Bluffs
Pinkletink Plantation
3 bedrooms, 5 beds
16–21 Oct
4.98 out of 5 average rating, 54 reviews
Home in Oak Bluffs
East Chop Oceanview Escape
6 bedrooms, 8 beds
21–27 Aug
5.0 out of 5 average rating, 4 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
4.94 out of 5 average rating, 17 reviews
Guest favourite
Home in Oak Bluffs
New Pristine Luxury Home on Martha's Vineyard
3 bedrooms, 6 beds
31 Aug – 5 Sept
4.98 out of 5 average rating, 86 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, 34 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
Top guest favourite
Home in Oak Bluffs
*NEW* 3 min drive to OB Circuit ave
5 bedrooms, 6 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 22 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
Superhost
Home in Oak Bluffs
Cozy, Central Island Family Home
5 bedrooms, 7 beds
26 Jul – 1 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Cottage in Oak Bluffs
111I Beautiful and walk to everything Oak Bluffs!
1 bedroom, 2 beds
13–18 Sept
4.97 out of 5 average rating, 183 reviews
Home in Oak Bluffs
Adorable Oak Bluffs Gingerbread House
4 bedrooms, 5 beds
19–26 Jun
5.0 out of 5 average rating, 3 reviews