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Search results; Over 1,000 homes in Oak Bluffs

Guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
2 bedrooms, 3 beds, 1 private bathroom
16–21 Oct
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4.93 out of 5 average rating, 309 reviews
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
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
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
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
Featured hotel
Hotel in Oak Bluffs
Water view double queen
1 bedroom, 1 bathroom
16–21 Sept
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
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
Gorgeous home in Oak Bluffs
4.8 out of 5 average rating, 5 reviews, 3 bedrooms, 3 beds, 3 bathrooms
28 Sept – 3 Oct
Superhost
Home in Oak Bluffs
Beach home just 0.8 miles to Farm Neck Golf Club!
4.77 out of 5 average rating, 131 reviews, 3 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
Home in Oak Bluffs
Oak Bluffs Oasis. Walk to town, beach & ferry.
New place to stay, 3 bedrooms, 3 beds, 1 bathroom
23–28 Aug
Top guest favourite
Flat in Oak Bluffs
Town/Beach: Vineyard Vacation Houses welcomes you!
4.93 out of 5 average rating, 154 reviews, 1 bedroom, 2 beds, 1 bathroom
26–31 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
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
Home in Oak Bluffs
Oak Bluffs Summer Home
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Jul
Guest favourite
Guest suite in Oak Bluffs
Cottage suite between the harbors: no minimum stay
4.79 out of 5 average rating, 344 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Guest favourite
Boutique hotel in Oak Bluffs
Balcony Room at the Tivoli Inn
4.91 out of 5 average rating, 54 reviews, 1 bedroom, 2 beds, 1 bathroom
22–27 Aug
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
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