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Search results; Over 1,000 homes in Oak Bluffs

Guest favourite
Flat in Oak Bluffs
Down island woodsy retreat.
1 bedroom, 2 beds, 1 private bathroom
12–17 Sept
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4.94 out of 5 average rating, 63 reviews
Featured hotel
Room in Oak Bluffs
Water view double queen
2 queen beds, 1 bathroom
23–28 Oct
Guest favourite
Home in Oak Bluffs
Oak Bluffs Victorian Walk to Town & Beaches
5 bedrooms, 7 beds, 5.5 bathrooms
29 Sept – 4 Oct
4.82 out of 5 average rating, 68 reviews
Top guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
2 bedrooms, 2 double beds, 1 bathroom
20–25 Sept
4.95 out of 5 average rating, 434 reviews
Superhost
Home in Oak Bluffs
Oak Bluffs 4BR • 5 Min Drive to Downtown
4 bedrooms, 4 beds, 2 bathrooms
18–23 Oct
4.88 out of 5 average rating, 69 reviews
Guest favourite
Home in Oak Bluffs
Charming 3-Bedroom Home in the Heart of Oak Bluffs
3 bedrooms, 3 beds, 2 bathrooms
15–20 Sept
4.95 out of 5 average rating, 20 reviews
Guest favourite
Home in Oak Bluffs
New Home Walk to Town & Beaches
4 bedrooms, 4 queen beds, 2.5 bathrooms
10–15 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Oak Bluffs
Casa Luca| Serene 3BR| SunRm, Outdr Shwr, A/C, BBQ
3 bedrooms, 5 beds, 1 bathroom
7–12 Sept
4.95 out of 5 average rating, 19 reviews
Guest favourite
Cottage in Oak Bluffs
111I Beautiful and walk to everything Oak Bluffs!
1 bedroom, 2 beds, 1.5 bathrooms
10–15 Oct
4.97 out of 5 average rating, 188 reviews
Top guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
2 bedrooms, 3 queen beds, 1 bathroom
19–24 Oct
4.93 out of 5 average rating, 319 reviews
Guest favourite
Home in Oak Bluffs
Studio apt in newly built barn
2 beds, 1 bathroom
28 Sept – 3 Oct
4.94 out of 5 average rating, 522 reviews
Guest favourite
Home in Oak Bluffs
impeccable cottage STEPS to downtown OB & beach!
3 bedrooms, 6 beds, 1 bathroom
20–25 Sept
4.92 out of 5 average rating, 212 reviews
Top guest favourite
Home in Oak Bluffs
Charming Oak Bluffs Retreat
6 bedrooms, 11 beds, 2.5 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 32 reviews
Top guest favourite
Home in Oak Bluffs
The Blue Lagoon, Oak Bluffs
3 bedrooms, 3 king beds, 3 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 54 reviews
Top guest favourite
Home in Oak Bluffs
**Vineyard Vacation Retreat** -3 BR
3 bedrooms, 3 beds, 2 bathrooms
8–13 Sept
4.96 out of 5 average rating, 134 reviews
Home in Oak Bluffs
Charming 3BR Cottage Near the Beach w/ Deck
3 bedrooms, 4 beds, 1 bathroom
1–7 Sept
Superhost
Home in Oak Bluffs
Oak Bluffs Allure
4 bedrooms, 4 beds, 5 bathrooms
7–12 Sept
Guest favourite
Home in Oak Bluffs
Vineyard Social-Spacious 5BR Home in Oak Bluffs
5 bedrooms, 9 beds, 4.5 bathrooms
14–19 Sept
4.93 out of 5 average rating, 113 reviews
Top guest favourite
Flat in Oak Bluffs
Cozy 3 bedroom apartment with King bed on Main St.
3 bedrooms, 5 beds, 1 bathroom
18–23 Oct
4.96 out of 5 average rating, 100 reviews