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Search results; Over 1,000 homes in Oak Bluffs

Top guest favourite
Guest house in Oak Bluffs
Mermaid Cottage
1 bedroom, 1 bed, 1 private bathroom
24–31 Jan
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4.99 out of 5 average rating, 101 reviews
Top guest favourite
Cabin in Oak Bluffs
Newly built rustic cabin in Oak Bluffs
1 bedroom, 1 bed, 1 bathroom
13–18 Sept
4.88 out of 5 average rating, 16 reviews
Superhost
Home in Oak Bluffs
Stunning OB retreat mins from best attractions
5 bedrooms, 8 beds, 3.5 bathrooms
27 Aug – 1 Sept
New place to stay
Top guest favourite
Guest suite in Oak Bluffs
Quiet Hide Away
1 bedroom, 1 queen bed, 1 bathroom
29 Aug – 3 Sept
4.98 out of 5 average rating, 204 reviews
Featured hotel
Room in Oak Bluffs
Queen
1 queen bed, 1 bathroom
29 Sept – 4 Oct
5.0 out of 5 average rating, 3 reviews
Top 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, 434 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, 521 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
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
111C Beautiful private condo walk to everything!
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.95 out of 5 average rating, 201 reviews
Top guest favourite
Home in Oak Bluffs
113A Walk to Town, beach and amazing location!
2 bedrooms, 2 beds, 1.5 bathrooms
7–12 Sept
4.95 out of 5 average rating, 218 reviews
Home in Oak Bluffs
Vineyard Family Home
3 bedrooms, 3 beds, 1 bathroom
1–6 Sept
Top guest favourite
Home in Oak Bluffs
Brand new! MV summer home!
3 bedrooms, 3 beds, 1 bathroom
26–31 Aug
5.0 out of 5 average rating, 9 reviews
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, 188 reviews
Superhost
Home in Oak Bluffs
Oak Bluffs Circuit Ave Cottage-Walk to Everything
4 bedrooms, 7 beds, 2 bathrooms
22–27 Aug
New place to stay
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, 565 reviews
Guest favourite
Room in Oak Bluffs
Oak Bluffs/ Harbor Views/ Queen Bed/ In Town
1 queen bed, 1 bathroom
24–29 Aug
4.91 out of 5 average rating, 120 reviews
Home in Edgartown
Peaceful get-a-way centrally located in Edgartown
4 bedrooms, 6 beds, 3 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Cottage in Tisbury
Not Your Great Aunt's Island Cottage
3 bedrooms, 5 beds, 1 bathroom
17–22 Oct
4.96 out of 5 average rating, 313 reviews