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Search results; Over 1,000 homes in Oak Bluffs

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, 55 reviews
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
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, 34 reviews
Guest favourite
Home in Oak Bluffs
Oak Bluffs Victorian Walk to Town & Beaches
5 bedrooms, 7 beds, 5.5 bathrooms
29 Sept – 4 Oct
4.81 out of 5 average rating, 70 reviews
Top guest favourite
Home in Oak Bluffs
**Vineyard Vacation Retreat** -3 BR
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 136 reviews
Guest favourite
Home in Oak Bluffs
impeccable cottage STEPS to downtown OB & beach!
3 bedrooms, 6 beds, 1 bathroom
19–24 Oct
4.92 out of 5 average rating, 212 reviews
Top guest favourite
Guest suite in Oak Bluffs
Quiet Hide Away
1 bedroom, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
4.98 out of 5 average rating, 207 reviews
Top guest favourite
Home in Oak Bluffs
Casa Luca| Serene 3BR| SunRm, Outdr Shwr, A/C, BBQ
3 bedrooms, 5 beds, 1 bathroom
4–9 Oct
4.95 out of 5 average rating, 21 reviews
Superhost
Home in Oak Bluffs
Oak Bluffs 4BR • 5 Min Drive to Downtown
4 bedrooms, 4 beds, 2 bathrooms
22–27 Oct
4.88 out of 5 average rating, 74 reviews
Top guest favourite
Cottage in Oak Bluffs
The WestLake
4 bedrooms, 5 beds, 2 bathrooms
24–29 Oct
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in Oak Bluffs
New Home Walk to Town & Beaches
4 bedrooms, 4 queen beds, 2.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Oak Bluffs
113A Walk to Town, beach and amazing location!
2 bedrooms, 2 beds, 1.5 bathrooms
18–23 Sept
4.94 out of 5 average rating, 223 reviews
Top guest favourite
Home in Oak Bluffs
Oak Bluffs Retreat, Walk to Town, Harbor, Ferries
3 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 17 reviews
Home in Oak Bluffs
Waterfront Retreat w/ Guest Cottage & Sunsets
4 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Oak Bluffs
Charming 3-Bedroom Home in the Heart of Oak Bluffs
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 23 reviews
Top guest favourite
Flat in Oak Bluffs
Town/Beach: Vineyard Vacation Houses welcomes you!
1 bedroom, 2 beds, 1 bathroom
18–23 Oct
4.89 out of 5 average rating, 314 reviews
Top guest favourite
Home in Oak Bluffs
Updated cottage/ ocean views
3 bedrooms, 4 beds, 1.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Home in Oak Bluffs
1/2 mile walk to Downtown Oak Bluffs
3 bedrooms, 7 beds, 2 bathrooms
17–22 Oct
4.97 out of 5 average rating, 37 reviews