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Search results; Over 1,000 homes in Oak Bluffs

Guest favourite
Apartment in Oak Bluffs
113B Cutest! Walk to Beach, Town and Harbor!
1 bedroom, 1 bed, 1 private bathroom
19–24 Aug
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4.9 out of 5 average rating, 268 reviews
Home in Tisbury
The Bird House
2 bedrooms, 3 beds, 2 bathrooms
8–14 Aug
New place to stay
Home in Oak Bluffs
Oak Bluffs Cottage Walk To Town
1 bedroom, 2 double beds, 1 bathroom
8–15 Aug
Top guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
2 bedrooms, 3 queen beds, 1 bathroom
16–21 Oct
4.93 out of 5 average rating, 313 reviews
Top guest favourite
Home in Oak Bluffs
113A Walk to Town, beach and amazing location!
2 bedrooms, 2 beds, 1.5 bathrooms
16–21 Aug
4.95 out of 5 average rating, 213 reviews
Top guest favourite
Home in Oak Bluffs
Casa Luca| Serene 3BR| SunRm, Outdr Shwr, A/C, BBQ
3 bedrooms, 5 beds, 1 bathroom
2–7 Aug
4.93 out of 5 average rating, 15 reviews
Home in Oak Bluffs
MV Sea Glenn Flower
4 bedrooms, 6 beds, 3 bathrooms
23–28 Aug
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, 426 reviews
Guest favourite
Guest suite in Oak Bluffs
Cottage suite between the harbors: no minimum stay
2 bedrooms, 3 beds, 1 bathroom
29 Aug – 3 Sept
4.79 out of 5 average rating, 347 reviews
Guest favourite
Flat in Oak Bluffs
111C Beautiful private condo walk to everything!
1 bedroom, 2 beds, 1 bathroom
16–21 Aug
4.95 out of 5 average rating, 195 reviews
Guest favourite
Cottage in Oak Bluffs
111H Beautiful clean walk to Town, Inkwell, harbor
1 bedroom, 2 beds, 1.5 bathrooms
13–18 Sept
4.95 out of 5 average rating, 193 reviews
Cabin in Oak Bluffs
Newly built rustic cabin in Oak Bluffs
1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 3 reviews
Home in Oak Bluffs
Waterfront Retreat w/ Guest Cottage & Sunsets
4 bedrooms, 5 beds, 2 bathrooms
31 Aug – 5 Sept
New place to stay
Guest favourite
Home in Oak Bluffs
Oak Bluffs Victorian Walk to Town & Beaches
5 bedrooms, 7 beds, 5.5 bathrooms
29 Sept – 4 Oct
4.83 out of 5 average rating, 66 reviews
Top guest favourite
Home in Oak Bluffs
Pinkletink Plantation
3 bedrooms, 5 beds, 2.5 bathrooms
16–21 Oct
4.98 out of 5 average rating, 53 reviews
Home in Oak Bluffs
Oak Bluffs Oasis. Walk to town, beach & ferry.
3 bedrooms, 3 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Oak Bluffs
14A Kennebec THE center of OB! No car, No problem!
1 bedroom, 2 beds, 1 bathroom
17–22 Aug
4.97 out of 5 average rating, 32 reviews
Guest favourite
Home in Oak Bluffs
New Serenity Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
1–6 Aug
5.0 out of 5 average rating, 7 reviews
Home in Oak Bluffs
Just listed! Bright, cozy, quiet & full of charm
3 bedrooms, 3 beds, 2 bathrooms
20–25 Aug
5.0 out of 5 average rating, 4 reviews