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Search results; Over 1,000 homes in Oak Bluffs

Superhost
Home in Oak Bluffs
3 beds, 3 baths 1.5 Miles to Downtown and Beaches!
3 bedrooms, 3 beds, 3 private bathrooms
21–26 Aug
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4.86 out of 5 average rating, 57 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
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
Place to stay in Oak Bluffs
Oak Bluffs Cottage Walk To Town
1 bedroom, 2 beds, 1 bathroom
8–15 Aug
Top guest favourite
Flat in Oak Bluffs
14A Kennebec THE center of OB! No car, No problem!
4.97 out of 5 average rating, 29 reviews, 1 bedroom, 2 beds, 1 bathroom
30 Jul – 4 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
3–8 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
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 Edgartown
Peaceful get-a-way centrally located in Edgartown
New place to stay, 4 bedrooms, 6 beds, 3 bathrooms
26–31 Jul
Superhost
Home in Oak Bluffs
NEW! Charming Oak Bluffs Cottage - Sleeps 8
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
17–22 Jul
Flat in Tisbury
Vineyard Sweet Escape
New place to stay, 1 bedroom, 2 beds, 1 bathroom
18–23 Jul
Top guest favourite
Home in Oak Bluffs
Pinkletink Plantation
4.98 out of 5 average rating, 53 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
10–15 Oct
Home in Oak Bluffs
Brand new! MV summer home!
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 3 beds, 1 bathroom
19–24 Jul
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
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
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
29 Jul – 3 Aug
Top guest favourite
Flat in Oak Bluffs
Beautiful and Short walk beach, town and harbor!
4.93 out of 5 average rating, 83 reviews, 1 bedroom, 2 beds, 1 bathroom
31 Jul – 5 Aug
Guest favourite
Home in Oak Bluffs
Diamond in The Bluffs - New Home, Private Backyard
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
18–23 Jul