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Search results; Over 1,000 homes in Oak Bluffs

Guest favourite
Boutique hotel in Oak Bluffs
Balcony Room at the Tivoli Inn
1 bedroom, 2 beds, 1 private bathroom
15–20 Sept
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4.91 out of 5 average rating, 57 reviews
Guest favourite
Home in Oak Bluffs
New Home Walk to Town & Beaches
4 bedrooms, 4 queen beds
11–16 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Oak Bluffs
The Blue Lagoon, Oak Bluffs
3 bedrooms, 3 king beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 55 reviews
Guest favourite
Home in Oak Bluffs
Oak Bluffs Victorian Walk to Town & Beaches
5 bedrooms, 7 beds
29 Sept – 4 Oct
4.81 out of 5 average rating, 70 reviews
Top guest favourite
Guest suite in Oak Bluffs
Quiet Hide Away
1 bedroom, 1 queen bed
27 Sept – 2 Oct
4.98 out of 5 average rating, 207 reviews
Top guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
2 bedrooms, 2 double beds
20–25 Sept
4.95 out of 5 average rating, 434 reviews
Featured hotel
Room in Oak Bluffs
Partial water view double queen
2 queen beds
21–26 Oct
Guest favourite
Home in Oak Bluffs
impeccable cottage STEPS to downtown OB & beach!
3 bedrooms, 6 beds
19–24 Oct
4.92 out of 5 average rating, 212 reviews
Guest favourite
Home in Oak Bluffs
Studio apt in newly built barn
2 beds
5–10 Oct
4.94 out of 5 average rating, 526 reviews
Guest favourite
Home in Oak Bluffs
**Vineyard Vacation Retreat** -3 BR
3 bedrooms, 3 beds
27 Sept – 2 Oct
4.96 out of 5 average rating, 135 reviews
Top guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
2 bedrooms, 3 queen beds
25–30 Oct
4.93 out of 5 average rating, 322 reviews
Top guest favourite
Flat in Oak Bluffs
Town/Beach: Vineyard Vacation Houses welcomes you!
1 bedroom, 2 beds
18–23 Oct
4.89 out of 5 average rating, 314 reviews
Top guest favourite
Flat in Oak Bluffs
14D Kennebec THE center of OB! No car, No problem!
1 bedroom, 2 beds
18–23 Sept
4.95 out of 5 average rating, 42 reviews
Top guest favourite
Home in Oak Bluffs
Brand new! MV summer home!
3 bedrooms, 3 beds
14–19 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Cabin in Oak Bluffs
Newly built rustic cabin in Oak Bluffs
1 bedroom, 1 bed
3–8 Oct
4.91 out of 5 average rating, 23 reviews
Guest favourite
Cottage in Oak Bluffs
111I Beautiful and walk to everything Oak Bluffs!
1 bedroom, 2 beds
10–15 Oct
4.97 out of 5 average rating, 191 reviews
Top guest favourite
Home in Oak Bluffs
Oak Bluffs Retreat, Walk to Town, Harbor, Ferries
3 bedrooms, 3 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Cottage in Oak Bluffs
The WestLake
4 bedrooms, 5 beds
24–29 Oct
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in Oak Bluffs
The Lighthouse
3 bedrooms, 6 beds
9–14 Sept
4.94 out of 5 average rating, 161 reviews