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Search results; Over 1,000 homes in Oak Bluffs

Guest favourite
Guest suite in Oak Bluffs
Cottage suite between the harbors: no minimum stay
2 bedrooms, 3 beds, 1 private bathroom
30 Aug – 4 Sept
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4.8 out of 5 average rating, 349 reviews
Home in Oak Bluffs
Oak Bluffs Cottage Walk To Town
1 bedroom, 2 beds, 1 bathroom
8–15 Aug
Home in Oak Bluffs
Amanda’s Veranda
New place to stay, 4 bedrooms, 5 beds, 3.5 bathrooms
22–27 Aug
Featured hotel
Room in Oak Bluffs
Water view double queen
2 queen beds, 1 bathroom
16–21 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
Top guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
4.95 out of 5 average rating, 426 reviews, 2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
Guest house in Oak Bluffs
Charming guesthouse in OB
4.88 out of 5 average rating, 8 reviews, 1 bedroom, 2 beds, 1 bathroom
1–6 Aug
Top guest favourite
Home in Oak Bluffs
113A Walk to Town, beach and amazing location!
4.95 out of 5 average rating, 213 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
16–21 Aug
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
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
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
Home in Oak Bluffs
MV Sea Glenn Flower
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 6 beds, 3 bathrooms
23–28 Aug
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
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
Room in Tisbury
Vineyard Haven Sanctuary- free bikes!
4.94 out of 5 average rating, 139 reviews, 1 queen bed, 1 bathroom
13–18 Sept
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
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
Flat in Oak Bluffs
Island Oasis
5.0 out of 5 average rating, 6 reviews, 1 bedroom, 3 beds, 1 bathroom
2–7 Aug
Top guest favourite
Flat in Oak Bluffs
14D Kennebec THE center of OB! No car, No problem!
4.94 out of 5 average rating, 32 reviews, 1 bedroom, 2 beds, 1 bathroom
16–21 Aug