filters

Search results; Over 1,000 homes in Oak Bluffs

Top guest favourite
Flat in Oak Bluffs
Sunny Studio Apartment on Martha's Vineyard
1 bedroom, 2 beds, 1 shared bathroom
23–28 Aug
,
4.98 out of 5 average rating, 232 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
Place to stay in Oak Bluffs
Oak Bluffs Cottage Walk To Town
1 bedroom, 2 beds, 1 bathroom
8–15 Aug
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
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
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
Superhost
Home in Oak Bluffs
Quintessential 1920s renovated bungalow new 2026!
New place to stay, 2 bedrooms, 2 beds, 1.5 bathrooms
23–28 Jul
Top guest favourite
Cottage in Oak Bluffs
Beautiful and walk to everything Oak Bluffs!
4.97 out of 5 average rating, 181 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
22–27 Aug
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
Cabin in Oak Bluffs
Newly built cabin walking distance from Oak Bluffs
New place to stay, 1 bedroom, 1 bed, 1 bathroom
21–26 Jul
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
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
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
Guest favourite
Home in Oak Bluffs
Casa Luca| Serene 3BR| SunRm, Outdr Shwr, A/C, BBQ
4.91 out of 5 average rating, 11 reviews, 3 bedrooms, 5 beds, 1 bathroom
28 Aug – 4 Sept
Home in Oak Bluffs
Amanda’s Veranda
New place to stay, 4 bedrooms, 5 beds, 3.5 bathrooms
17–22 Jul
Guest favourite
Home in Oak Bluffs
New Serenity Retreat
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
9–14 Jul