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Search results; Over 1,000 homes in Oak Bluffs

Top guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
2 bedrooms, 3 beds, 1 private bathroom
16–21 Oct
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4.93 out of 5 average rating, 313 reviews
Room in Oak Bluffs
Oak Bluffs Cottage Walk To Town
2 double beds
8–15 Aug
Top guest favourite
Home in Oak Bluffs
113A Walk to Town, beach and amazing location!
2 bedrooms, 2 beds
16–21 Aug
4.95 out of 5 average rating, 213 reviews
Top guest favourite
Flat in Oak Bluffs
111C Beautiful private condo walk to everything!
1 bedroom, 2 beds
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
30 Aug – 4 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
30 Aug – 4 Sept
New place to stay
Guest favourite
Guest suite in Oak Bluffs
Cottage suite between the harbors: no minimum stay
2 bedrooms, 3 beds
29 Aug – 3 Sept
4.79 out of 5 average rating, 347 reviews
Top guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
2 bedrooms, 2 double beds
18–23 Oct
4.95 out of 5 average rating, 426 reviews
Top guest favourite
Home in Oak Bluffs
Casa Luca| Serene 3BR| SunRm, Outdr Shwr, A/C, BBQ
3 bedrooms, 5 beds
2–7 Aug
4.93 out of 5 average rating, 15 reviews
Home in Oak Bluffs
MV Sea Glenn Flower
4 bedrooms, 6 beds
23–28 Aug
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
17–22 Aug
4.97 out of 5 average rating, 32 reviews
Home in Oak Bluffs
Oak Bluffs Oasis. Walk to town, beach & ferry.
3 bedrooms, 3 beds
7–12 Sept
5.0 out of 5 average rating, 3 reviews
Flat in Oak Bluffs
Island Oasis
1 bedroom, 3 beds
2–7 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Oak Bluffs
Pinkletink Plantation
3 bedrooms, 5 beds
10–15 Oct
4.98 out of 5 average rating, 53 reviews
Top guest favourite
Room in Tisbury
Vineyard Haven Sanctuary- free bikes!
1 queen bed
13–18 Sept
4.94 out of 5 average rating, 139 reviews
Guest favourite
Home in Oak Bluffs
New Serenity Retreat
2 bedrooms, 3 beds
1–6 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Oak Bluffs
Walk East Chop from Dover House
5 bedrooms, 7 beds
21–26 Sept
5.0 out of 5 average rating, 33 reviews
Home in Oak Bluffs
East Chop Oceanview Escape
6 bedrooms, 8 beds
21–27 Aug
5.0 out of 5 average rating, 4 reviews
Home in Oak Bluffs
Just listed! Bright, cozy, quiet & full of charm
3 bedrooms, 3 beds
20–25 Aug
5.0 out of 5 average rating, 4 reviews