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Search results; Over 1,000 homes in Oak Bluffs

Guest favourite
Cottage in Oak Bluffs
East Chop Cottage - walk to lighthouse & beach!
1 bedroom, 1 bed, 0.5 private bathroom
20–25 Sept
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4.9 out of 5 average rating, 149 reviews
Top guest favourite
Cabin in Oak Bluffs
Newly built rustic cabin in Oak Bluffs
1 bedroom, 1 bed
13–18 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
2 bedrooms, 2 double beds
18–23 Oct
4.95 out of 5 average rating, 431 reviews
Top guest favourite
Guest suite in Oak Bluffs
Quiet Hide Away
1 bedroom, 1 queen bed
20–25 Aug
4.98 out of 5 average rating, 202 reviews
Guest favourite
Home in Oak Bluffs
Studio apt in newly built barn
2 beds
28 Sept – 3 Oct
4.94 out of 5 average rating, 519 reviews
Featured hotel
Room in Oak Bluffs
Water view double queen
2 queen beds
20–25 Sept
Top guest favourite
Room in Tisbury
Vineyard Haven Sanctuary- free bikes!
1 queen bed
20–25 Sept
4.94 out of 5 average rating, 139 reviews
Top guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
2 bedrooms, 3 queen beds
19–24 Oct
4.93 out of 5 average rating, 316 reviews
Top guest favourite
Home in Oak Bluffs
113A Walk to Town, beach and amazing location!
2 bedrooms, 2 beds
7–12 Sept
4.95 out of 5 average rating, 217 reviews
Guest favourite
Home in Oak Bluffs
Brand new! MV summer home!
3 bedrooms, 3 beds
26–31 Aug
5.0 out of 5 average rating, 8 reviews
Home in Oak Bluffs
Amanda’s Veranda
4 bedrooms, 5 beds
27 Sept – 2 Oct
New place to stay
Guest favourite
Home in Oak Bluffs
Central location for your vacation
2 bedrooms, 2 queen beds
26 Sept – 1 Oct
4.79 out of 5 average rating, 259 reviews
Top guest favourite
Home in Oak Bluffs
Pinkletink Plantation
3 bedrooms, 5 beds
16–21 Oct
4.98 out of 5 average rating, 58 reviews
Top guest favourite
Cottage in Oak Bluffs
111I Beautiful and walk to everything Oak Bluffs!
1 bedroom, 2 beds
18–23 Sept
4.97 out of 5 average rating, 186 reviews
Top guest favourite
Cottage in Tisbury
Not Your Great Aunt's Island Cottage
3 bedrooms, 5 beds
17–22 Oct
4.96 out of 5 average rating, 313 reviews
Home in Oak Bluffs
Waterfront Retreat w/ Guest Cottage & Sunsets
4 bedrooms, 5 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 3 reviews
Guest favourite
Cottage in Oak Bluffs
111H Beautiful clean walk to Town, Inkwell, harbor
1 bedroom, 2 beds
13–18 Sept
4.95 out of 5 average rating, 198 reviews
Top guest favourite
Flat in Oak Bluffs
Town/Beach: Vineyard Vacation Houses welcomes you!
1 bedroom, 2 beds
15–20 Oct
4.89 out of 5 average rating, 309 reviews
Guest favourite
Guest suite in Oak Bluffs
Oak Bluffs Star
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.94 out of 5 average rating, 243 reviews