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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
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
16–21 Jul
Guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
4.93 out of 5 average rating, 308 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Oct
Guest favourite
Cottage in Oak Bluffs
Beautiful clean walk to Town, Inkwell and harbor!
4.95 out of 5 average rating, 189 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
22–27 Jul
Guest favourite
Guest suite in Oak Bluffs
Cottage suite between the harbors: no minimum stay
4.79 out of 5 average rating, 341 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Guest favourite
Flat in Oak Bluffs
14C Kennebec THE center of OB! No car, No problem!
5.0 out of 5 average rating, 19 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Place to stay in Oak Bluffs
Oak Bluffs Cottage Walk To Town
1 bedroom, 2 beds, 1 bathroom
8–15 Aug
Top guest favourite
Home in Oak Bluffs
**Vineyard Vacation Retreat** -3 BR
4.96 out of 5 average rating, 125 reviews, 3 bedrooms, 3 beds, 2 bathrooms
8–13 Sept
Guest favourite
Home in Oak Bluffs
Oak Bluffs Victorian Walk to Town & Beaches
4.83 out of 5 average rating, 65 reviews, 5 bedrooms, 7 beds, 5.5 bathrooms
18–23 Sept
Guest favourite
Home in Oak Bluffs
New Pristine Luxury Home on Martha's Vineyard
4.98 out of 5 average rating, 81 reviews, 3 bedrooms, 6 beds, 2.5 bathrooms
29 Sept – 4 Oct
Guest favourite
Home in Oak Bluffs
Casa Luca| Serene 3BR| SunRm, Outdr Shwr, A/C, BBQ
4.92 out of 5 average rating, 12 reviews, 3 bedrooms, 5 beds, 1 bathroom
28 Aug – 4 Sept
Guest favourite
Home in Oak Bluffs
Walk to Town, beach and amazing location 113A
4.95 out of 5 average rating, 209 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
16–21 Aug
Guest favourite
Apartment in Oak Bluffs
Stunning. Walk to Beach, Town and Harbor 113B
4.9 out of 5 average rating, 264 reviews, 1 bedroom, 1 bed, 1 bathroom
31 Jul – 5 Aug
Guest favourite
Cottage in Oak Bluffs
Beautiful walk to Town, Inkwell and harbor!
4.95 out of 5 average rating, 217 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
27 Jul – 1 Aug
Home in Oak Bluffs
Brand new! MV summer home!
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 3 beds, 1 bathroom
14–19 Jul
Superhost
Place to stay in Oak Bluffs
Oak Bluffs Circuit Av Walk Everywhere Single Room
1 bedroom, 1 bed, 1 bathroom
10–15 Jul
Superhost
Home in Oak Bluffs
Hidden home in the North Bluff
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 3 beds, 3 bathrooms
6–11 Sept
Home in Oak Bluffs
Amanda’s Veranda
New place to stay, 4 bedrooms, 5 beds, 3.5 bathrooms
17–22 Jul
Superhost
Home in Oak Bluffs
Martha’s Vineyard Boutique Beach Cottage!
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 6 beds, 2 bathrooms
26–31 Aug