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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, 138 reviews
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Featured hotel
Hotel in Oak Bluffs
King
1 bedroom, 1 king bed
25–30 Oct
5.0 out of 5 average rating, 7 reviews
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Guest favourite
Home in Oak Bluffs
Studio apt in newly built barn
2 beds
5–10 Oct
4.94 out of 5 average rating, 527 reviews
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Top guest favourite
Cabin in Oak Bluffs
Newly built rustic cabin in Oak Bluffs
1 bedroom, 1 bed
3–8 Oct
4.92 out of 5 average rating, 26 reviews
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Top guest favourite
Guest suite in Oak Bluffs
Quiet Hide Away
1 bedroom, 1 queen bed
27 Sept – 2 Oct
4.98 out of 5 average rating, 209 reviews
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Guest favourite
Cottage in Oak Bluffs
East Chop Cottage - walk to lighthouse & beach!
1 bedroom, 1 queen bed
20–25 Sept
4.9 out of 5 average rating, 155 reviews
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Guest favourite
Home in Oak Bluffs
Oak Bluffs Victorian Walk to Town & Beaches
5 bedrooms, 7 beds
29 Sept – 4 Oct
4.82 out of 5 average rating, 71 reviews
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Guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
2 bedrooms, 2 double beds
20–25 Sept
4.95 out of 5 average rating, 440 reviews
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Top guest favourite
Home in Oak Bluffs
The Blue Lagoon, Oak Bluffs
3 bedrooms, 3 king beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 56 reviews
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Top guest favourite
Home in Oak Bluffs
Charming Oak Bluffs Retreat
6 bedrooms, 11 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 35 reviews
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Guest favourite
Home in Oak Bluffs
Pinkletink Plantation
3 bedrooms, 5 beds
20–25 Oct
4.97 out of 5 average rating, 61 reviews
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Guest favourite
Home in Oak Bluffs
impeccable cottage STEPS to downtown OB & beach!
3 bedrooms, 6 beds
19–24 Oct
4.92 out of 5 average rating, 212 reviews
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Top guest favourite
Home in Oak Bluffs
Beachfront Oasis
4 bedrooms, 5 beds
4–11 Oct
4.93 out of 5 average rating, 15 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
4–9 Oct
4.95 out of 5 average rating, 21 reviews
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Top guest favourite
Guest suite in Oak Bluffs
Spacious 1 Bedroom Apt - 3 min walk to the Beach!
1 bedroom, 2 beds
20–25 Sept
5.0 out of 5 average rating, 43 reviews
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Top guest favourite
Cottage in Oak Bluffs
The WestLake
4 bedrooms, 5 beds
24–29 Oct
5.0 out of 5 average rating, 14 reviews
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Guest favourite
Home in Oak Bluffs
New Home Walk to Town & Beaches
4 bedrooms, 4 queen beds
1–6 Nov
5.0 out of 5 average rating, 11 reviews
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Top guest favourite
Flat in Oak Bluffs
Town/Beach: Vineyard Vacation Houses welcomes you!
1 bedroom, 2 beds
18–23 Oct
4.89 out of 5 average rating, 314 reviews
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Top guest favourite
Guest house in Oak Bluffs
Oak bluffs cottage Perfect place to honeymoon!
2 bedrooms, 2 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 138 reviews