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Search results; Over 1,000 homes in Oak Bluffs

Guest favourite
Home in Oak Bluffs
Central location for your vacation
2 bedrooms, 2 beds, 1 private bathroom
29 Aug – 3 Sept
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4.79 out of 5 average rating, 259 reviews
Home in Oak Bluffs
Amanda’s Veranda
New place to stay, 4 bedrooms, 5 beds, 3.5 bathrooms
30 Aug – 4 Sept
Top guest favourite
Flat in Oak Bluffs
14B Kennebec THE center of OB! No car, No problem!
4.91 out of 5 average rating, 22 reviews, 1 bedroom, 2 beds, 1 bathroom
17–22 Aug
Top guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
4.95 out of 5 average rating, 427 reviews, 2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
Featured hotel
Room in Oak Bluffs
Water view double queen
2 queen beds, 1 bathroom
16–21 Sept
Guest favourite
Cottage in Oak Bluffs
111G Beautiful walk to Town, Inkwell and harbor!
4.94 out of 5 average rating, 222 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
24–29 Aug
Top guest favourite
Home in Oak Bluffs
Spectacular beach & pool combo; beautiful sunsets!
4.93 out of 5 average rating, 221 reviews, 4 bedrooms, 5 beds, 5.5 bathrooms
4–9 Oct
Top guest favourite
Room in Tisbury
Vineyard Haven Sanctuary- free bikes!
4.94 out of 5 average rating, 139 reviews, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
Top guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
4.93 out of 5 average rating, 313 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Oct
Top guest favourite
Home in Oak Bluffs
Casa Luca| Serene 3BR| SunRm, Outdr Shwr, A/C, BBQ
4.93 out of 5 average rating, 15 reviews, 3 bedrooms, 5 beds, 1 bathroom
28 Aug – 4 Sept
Top guest favourite
Home in Tisbury
Sunny, Spacious Vineyard Retreat
4.97 out of 5 average rating, 302 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
20–25 Sept
Cabin in Oak Bluffs
Newly built rustic cabin in Oak Bluffs
5.0 out of 5 average rating, 4 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
Home in Edgartown
Water Street Edgartown
4.86 out of 5 average rating, 7 reviews, 5 bedrooms, 6 beds, 3.5 bathrooms
15–20 Sept
Top guest favourite
Home in Oak Bluffs
Charming Oak Bluffs Retreat
4.96 out of 5 average rating, 28 reviews, 6 bedrooms, 11 beds, 2.5 bathrooms
27 Sept – 2 Oct
Guest favourite
Home in Oak Bluffs
Beautiful Home in Oak Bluffs Center!
5.0 out of 5 average rating, 47 reviews, 3 bedrooms, 6 beds, 1 bathroom
16–21 Sept
Flat in Oak Bluffs
Island Oasis
5.0 out of 5 average rating, 6 reviews, 1 bedroom, 3 beds, 1 bathroom
2–7 Aug
Home in Oak Bluffs
Waterfront Retreat w/ Guest Cottage & Sunsets
New place to stay, 4 bedrooms, 5 beds, 2 bathrooms
31 Aug – 5 Sept
Home in Oak Bluffs
Charming 3BR Cottage Near the Beach w/ Deck
3 bedrooms, 4 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Home in Tisbury
Martha’s Vineyard Waterfront Private Beach
5.0 out of 5 average rating, 18 reviews, 8 bedrooms, 10 beds, 5.5 bathrooms
20–25 Sept