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Search results; Over 1,000 homes in Oak Bluffs

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Guest favourite
Home in Oak Bluffs
impeccable cottage STEPS to downtown OB & beach!
3 bedrooms, 6 beds, 1 private bathroom
19–24 Oct
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4.92 out of 5 average rating, 213 reviews
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Featured hotel
Hotel in Oak Bluffs
Summercamp, Queen
1 bedroom, 1 queen bed, 1 bathroom
13–18 Oct
5.0 out of 5 average rating, 4 reviews
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Featured hotel
Hotel in Oak Bluffs
Morgan Hotel, Partial Ocean View King with Verand.
1 bedroom, 1 king bed, 1 bathroom
4–9 Oct
New place to stay
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Top guest favourite
Cabin in Oak Bluffs
Newly built rustic cabin in Oak Bluffs
1 bedroom, 1 bed, 1 bathroom
17–22 Oct
4.85 out of 5 average rating, 27 reviews
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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, 442 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
1–6 Oct
4.82 out of 5 average rating, 73 reviews
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Top guest favourite
Flat in Oak Bluffs
Town/Beach: Vineyard Vacation Houses welcomes you!
1 bedroom, 2 beds, 1 bathroom
18–23 Oct
4.89 out of 5 average rating, 315 reviews
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Top guest favourite
Flat in Oak Bluffs
Cozy 3 bedroom apartment with King bed on Main St.
3 bedrooms, 5 beds, 1 bathroom
18–23 Oct
4.96 out of 5 average rating, 102 reviews
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Top guest favourite
Home in Oak Bluffs
Charming Oak Bluffs Retreat
6 bedrooms, 11 beds, 2.5 bathrooms
5–10 Oct
4.97 out of 5 average rating, 35 reviews
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Guest favourite
Home in Oak Bluffs
New Home Walk to Town & Beaches
4 bedrooms, 4 queen beds, 2.5 bathrooms
1–6 Nov
5.0 out of 5 average rating, 11 reviews
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Top guest favourite
Home in Oak Bluffs
The Blue Lagoon, Oak Bluffs
3 bedrooms, 3 king beds, 3 bathrooms
11–16 Oct
4.98 out of 5 average rating, 57 reviews
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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, 193 reviews
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Superhost
Home in Oak Bluffs
Oak Bluffs 4BR • 5 Min Drive to Downtown
4 bedrooms, 4 beds, 2 bathrooms
22–27 Oct
4.88 out of 5 average rating, 76 reviews
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Guest favourite
Home in Oak Bluffs
**Vineyard Vacation Retreat** -3 BR
3 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
4.96 out of 5 average rating, 140 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, 21 reviews
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Top guest favourite
Guest suite in Oak Bluffs
Quiet Hide Away
1 bedroom, 1 queen bed, 1 bathroom
1–6 Oct
4.98 out of 5 average rating, 210 reviews
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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, 527 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
10–15 Oct
4.95 out of 5 average rating, 206 reviews
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Top guest favourite
Home in Oak Bluffs
Updated cottage/ ocean views
3 bedrooms, 4 beds, 1.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 28 reviews