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Search results; Over 1,000 homes in Oak Bluffs

Apartment in Oak Bluffs
Breezy Oak Bluffs Condo - Steps to Inkwell Beach!
2 bedrooms, 3 beds, 2 bathrooms
11–16 Oct
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4.91 out of 5 average rating, 22 reviews
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
Place to stay in Oak Bluffs
Oak Bluffs Cottage Walk To Town
1 bedroom, 2 beds, 1 bathroom
8–15 Aug
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
1–6 Aug
Top guest favourite
Cottage in Oak Bluffs
The WestLake
5.0 out of 5 average rating, 10 reviews, 4 bedrooms, 5 beds, 2 bathrooms
26 Sept – 1 Oct
Guest favourite
Guest suite in Oak Bluffs
Cottage suite between the harbors: no minimum stay
4.79 out of 5 average rating, 345 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Top guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
4.95 out of 5 average rating, 424 reviews, 2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
Top guest favourite
Flat in Oak Bluffs
Beautiful private apartment walk to everything!
4.95 out of 5 average rating, 194 reviews, 1 bedroom, 2 beds, 1 bathroom
21–26 Jul
Guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
4.93 out of 5 average rating, 309 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Oct
Home in Oak Bluffs
Brand new! MV summer home!
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 3 beds, 1 bathroom
19–24 Jul
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
Top guest favourite
Home in Oak Bluffs
Pinkletink Plantation
4.98 out of 5 average rating, 52 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
10–15 Oct
Guest favourite
Flat in Oak Bluffs
14B Kennebec THE center of OB! No car, No problem!
4.94 out of 5 average rating, 17 reviews, 1 bedroom, 2 beds, 1 bathroom
3–8 Aug
Superhost
Home in Oak Bluffs
Quintessential 1920s renovated bungalow new 2026!
New place to stay, 2 bedrooms, 2 beds, 1.5 bathrooms
30 Jul – 4 Aug
Home in Oak Bluffs
OB Salt & Cedar Cottage
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 9 beds, 2 bathrooms
24–31 Aug
Top guest favourite
Home in Oak Bluffs
** Vineyard Vacation Retreat ** with HOT TUB
4.92 out of 5 average rating, 144 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
19–24 Sept
Home in Oak Bluffs
Oak Bluffs Summer Home
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Jul
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
Home in Oak Bluffs
Casa Luca| Serene 3BR| SunRm, Outdr Shwr, A/C, BBQ
4.92 out of 5 average rating, 13 reviews, 3 bedrooms, 5 beds, 1 bathroom
28 Aug – 4 Sept