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Search results; Over 1,000 homes in Oak Bluffs

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Top guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
2 bedrooms, 3 beds, 1 private bathroom
25–30 Oct
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4.93 out of 5 average rating, 326 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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Top guest favourite
Cabin in Oak Bluffs
Newly built rustic cabin in Oak Bluffs
1 bedroom, 1 bed, 1 bathroom
17–22 Oct
4.92 out of 5 average rating, 26 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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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, 75 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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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
Charming Oak Bluffs Retreat
6 bedrooms, 11 beds, 2.5 bathrooms
1–6 Oct
4.97 out of 5 average rating, 35 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
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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Guest favourite
Home in Oak Bluffs
Charming 3-Bedroom Home in the Heart of Oak Bluffs
3 bedrooms, 3 beds, 2 bathrooms
4–9 Oct
4.96 out of 5 average rating, 24 reviews
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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
8–13 Oct
4.96 out of 5 average rating, 45 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, 209 reviews
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Guest favourite
Apartment in Oak Bluffs
113B Cutest! Walk to Beach, Town and Harbor!
1 bedroom, 1 queen bed, 1 bathroom
1–6 Oct
4.9 out of 5 average rating, 273 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
Boutique hotel in Oak Bluffs
In Town Queen Room
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.96 out of 5 average rating, 81 reviews
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Top guest favourite
Home in Oak Bluffs
#CozyBluffs #OakBluffs Walk to Beach/Town/Ferries
1 bedroom, 1 king bed, 1.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 29 reviews
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Guest favourite
Home in Oak Bluffs
113A Walk to Town, beach and amazing location!
2 bedrooms, 2 beds, 1.5 bathrooms
3–8 Oct
4.94 out of 5 average rating, 225 reviews