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Search results; Over 1,000 homes in Oak Bluffs

Top guest favourite
Cottage in Oak Bluffs
East Chop Cottage - walk to lighthouse & beach!
1 bedroom, 1 bed, 0.5 private bathroom
25–30 Aug
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4.9 out of 5 average rating, 143 reviews
Superhost
Home in Oak Bluffs
NEW! Charming Oak Bluffs Cottage - Sleeps 8
3 bedrooms, 4 beds
16–21 Jul
New place to stay
Home in Oak Bluffs
Amanda’s Veranda
4 bedrooms, 5 beds
1–6 Aug
New place to stay
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, 309 reviews
Guest favourite
Cottage in Oak Bluffs
Beautiful clean walk to Town, Inkwell and harbor!
1 bedroom, 2 beds
22–27 Jul
4.95 out of 5 average rating, 189 reviews
Guest favourite
Home in Oak Bluffs
Walk to Town, beach and amazing location 113A
2 bedrooms, 2 beds
16–21 Aug
4.95 out of 5 average rating, 209 reviews
Place to stay in Oak Bluffs
Oak Bluffs Cottage Walk To Town
1 bedroom, 2 double beds
8–15 Aug
Guest favourite
Home in Oak Bluffs
New Pristine Luxury Home on Martha's Vineyard
3 bedrooms, 6 beds
29 Sept – 4 Oct
4.98 out of 5 average rating, 81 reviews
Top guest favourite
Home in Oak Bluffs
Pinkletink Plantation
3 bedrooms, 5 beds
10–15 Oct
4.98 out of 5 average rating, 52 reviews
Cabin in Oak Bluffs
Newly built cabin walking distance from Oak Bluffs
1 bedroom, 1 bed
21–26 Jul
New place to stay
Superhost
Home in Oak Bluffs
Martha’s Vineyard Boutique Beach Cottage!
3 bedrooms, 6 beds
26–31 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Oak Bluffs
14A Kennebec THE center of OB! No car, No problem!
1 bedroom, 2 beds
20–25 Jul
4.97 out of 5 average rating, 29 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
The Oak Bluffs House - Walk to Beach & Town
2 bedrooms, 3 beds
12–17 Jul
5.0 out of 5 average rating, 138 reviews
Home in Oak Bluffs
OB Salt & Cedar Cottage
4 bedrooms, 9 beds
17–24 Aug
5.0 out of 5 average rating, 3 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, 424 reviews
Guest favourite
Guest suite in Oak Bluffs
Cottage suite between the harbors: no minimum stay
2 bedrooms, 3 beds
19–24 Jul
4.79 out of 5 average rating, 343 reviews
Superhost
Home in Oak Bluffs
Hidden home in the North Bluff
3 bedrooms, 3 beds
6–11 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Oak Bluffs
Beautiful and Short walk beach, town and harbor!
1 bedroom, 2 beds
31 Jul – 5 Aug
4.93 out of 5 average rating, 82 reviews