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Search results; Over 1,000 homes in Oak Bluffs

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Top guest favourite
Home in Oak Bluffs
**Vineyard Vacation Retreat** -3 BR
3 bedrooms, 3 beds, 2 private bathrooms
27 Sept – 2 Oct
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4.96 out of 5 average rating, 135 reviews
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Home in Oak Bluffs
New Home Walk to Town & Beaches
4 bedrooms, 4 queen beds, 2.5 bathrooms
10–15 Sept
5.0 out of 5 average rating, 11 reviews
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Guest favourite
Home in Oak Bluffs
Oak Bluffs Victorian Walk to Town & Beaches
5 bedrooms, 7 beds, 5.5 bathrooms
29 Sept – 4 Oct
4.82 out of 5 average rating, 68 reviews
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Top guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
2 bedrooms, 2 double beds, 1 bathroom
20–25 Sept
4.95 out of 5 average rating, 434 reviews
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Guest favourite
Home in Oak Bluffs
impeccable cottage STEPS to downtown OB & beach!
3 bedrooms, 6 beds, 1 bathroom
19–24 Oct
4.92 out of 5 average rating, 212 reviews
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Top guest favourite
Cabin in Oak Bluffs
Newly built rustic cabin in Oak Bluffs
1 bedroom, 1 bed, 1 bathroom
3–8 Oct
4.89 out of 5 average rating, 19 reviews
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Top guest favourite
Guest suite in Oak Bluffs
Quiet Hide Away
1 bedroom, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
4.98 out of 5 average rating, 206 reviews
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Top guest favourite
Home in Oak Bluffs
Casa Luca| Serene 3BR| SunRm, Outdr Shwr, A/C, BBQ
3 bedrooms, 5 beds, 1 bathroom
4–9 Oct
4.95 out of 5 average rating, 19 reviews
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Home in Oak Bluffs
113A Walk to Town, beach and amazing location!
2 bedrooms, 2 beds, 1.5 bathrooms
18–23 Sept
4.95 out of 5 average rating, 219 reviews
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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, 201 reviews
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Top guest favourite
Cottage in Oak Bluffs
111I Beautiful and walk to everything Oak Bluffs!
1 bedroom, 2 beds, 1.5 bathrooms
10–15 Oct
4.97 out of 5 average rating, 189 reviews
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Top guest favourite
Cottage in Oak Bluffs
The WestLake
4 bedrooms, 5 beds, 2 bathrooms
24–29 Oct
5.0 out of 5 average rating, 12 reviews
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Top guest favourite
Home in Oak Bluffs
Charming Oak Bluffs Retreat
6 bedrooms, 11 beds, 2.5 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 33 reviews
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Home in Oak Bluffs
Vineyard Family Home
3 bedrooms, 3 beds, 1 bathroom
8–13 Sept
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Top guest favourite
Flat in Oak Bluffs
14D Kennebec THE center of OB! No car, No problem!
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
4.95 out of 5 average rating, 38 reviews
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Guest favourite
Home in Oak Bluffs
The Lighthouse
3 bedrooms, 6 beds, 2 bathrooms
6–11 Sept
4.94 out of 5 average rating, 161 reviews
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Guest favourite
Home in Oak Bluffs
Beach home just 0.8 miles to Farm Neck Golf Club!
3 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
4.79 out of 5 average rating, 140 reviews
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Top guest favourite
Home in Oak Bluffs
The Blue Lagoon, Oak Bluffs
3 bedrooms, 3 king beds, 3 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 55 reviews
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Top guest favourite
Home in Oak Bluffs
Studio apt in newly built barn
2 beds, 1 bathroom
5–10 Oct
4.94 out of 5 average rating, 525 reviews