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Search results; Over 1,000 homes in Oak Bluffs

Guest favourite
Home in Oak Bluffs
impeccable cottage STEPS to downtown OB & beach!
3 bedrooms, 6 beds, 1 private bathroom
20–25 Sept
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4.92 out of 5 average rating, 211 reviews
Top guest favourite
Cabin in Oak Bluffs
Newly built rustic cabin in Oak Bluffs
1 bedroom, 1 bed, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
2 bedrooms, 2 double beds, 1 bathroom
18–23 Oct
4.95 out of 5 average rating, 428 reviews
Featured hotel
Room in Oak Bluffs
Water view double queen
2 queen beds, 1 bathroom
17–22 Sept
Guest favourite
Home in Oak Bluffs
Studio apt in newly built barn
2 beds, 1 bathroom
27 Sept – 2 Oct
4.94 out of 5 average rating, 519 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, 316 reviews
Top guest favourite
Guest suite in Oak Bluffs
Quiet Hide Away
1 bedroom, 1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 200 reviews
Top guest favourite
Room in Tisbury
Vineyard Haven Sanctuary- free bikes!
1 queen bed, 1 bathroom
27 Sept – 2 Oct
4.94 out of 5 average rating, 139 reviews
Top guest favourite
Flat in Oak Bluffs
Town/Beach: Vineyard Vacation Houses welcomes you!
1 bedroom, 2 beds, 1 bathroom
15–20 Oct
4.89 out of 5 average rating, 308 reviews
Guest favourite
Room in Oak Bluffs
Capricorn House on the beach - Room #5
1 bed, 1 bathroom
2–7 Oct
5.0 out of 5 average rating, 8 reviews
Home in Oak Bluffs
Waterfront Retreat w/ Guest Cottage & Sunsets
4 bedrooms, 5 beds, 2 bathrooms
27 Sept – 2 Oct
Guest favourite
Home in Tisbury
Vineyard Haven Walk to Ferry
3 bedrooms, 5 beds, 2 bathrooms
18–23 Oct
4.93 out of 5 average rating, 187 reviews
Top guest favourite
Cottage in Oak Bluffs
111I Beautiful and walk to everything Oak Bluffs!
1 bedroom, 2 beds, 1.5 bathrooms
19–24 Aug
4.97 out of 5 average rating, 184 reviews
Top guest favourite
Room in Oak Bluffs
Ocean Park Victorian
1 double bed, 1 bathroom
22–27 Nov
4.99 out of 5 average rating, 226 reviews
Top guest favourite
Cottage in Tisbury
Not Your Great Aunt's Island Cottage
3 bedrooms, 5 beds, 1 bathroom
8–13 Oct
4.96 out of 5 average rating, 313 reviews
Guest favourite
Home in Oak Bluffs
Central location for your vacation
2 bedrooms, 2 queen beds, 1 bathroom
4–9 Oct
4.79 out of 5 average rating, 259 reviews
Top guest favourite
Rooms in Edgartown
The Alison Boylston Piazza House
2 bedrooms, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.85 out of 5 average rating, 562 reviews
Home in Oak Bluffs
Oak Bluffs Summer Home
3 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
New place to stay
Superhost
Home in Oak Bluffs
Oak Bluffs 4BR • 5 Min Drive to Downtown
4 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
4.88 out of 5 average rating, 66 reviews