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Search results; Over 1,000 homes in Oakland

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Guest favourite
Home in Oakland
Sunlit Lakefront w/ Dock, Game Room & Firepit
4 bedrooms, 8 beds, 4.5 private bathrooms
27 Sept – 2 Oct
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5.0 out of 5 average rating, 6 reviews
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Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds
12–17 Oct
4.88 out of 5 average rating, 112 reviews
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Flat in Oakland
Large 2-bdrm apt. Walking distance to everything
2 bedrooms, 2 beds
28 Dec – 2 Jan
4.82 out of 5 average rating, 84 reviews
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Top guest favourite
Home in Oakland
Historic 6BR Family Getaway
6 bedrooms, 7 beds
18–23 Oct
5.0 out of 5 average rating, 8 reviews
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Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds
4–9 Oct
4.88 out of 5 average rating, 32 reviews
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Top guest favourite
Home in McHenry
Newly Renovated 2 Bed/2 Bath in Deep Creek
2 bedrooms, 2 queen beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 397 reviews
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Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds
20–25 Sept
4.98 out of 5 average rating, 170 reviews
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Flat in Oakland
Cozy studio nook, close to everything
1 bedroom, 1 double bed
27 Sept – 4 Oct
4.63 out of 5 average rating, 70 reviews
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Guest favourite
Cabin in Terra Alta
Secluded Mountain Lake Escape w/ Dock & Kayaks
4 bedrooms, 4 beds
30 Nov – 5 Dec
4.89 out of 5 average rating, 55 reviews
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Top guest favourite
Home in Oakland
Deep Creek Dome Cabin | Fire Pit & EV Near Wisp
4 bedrooms, 6 beds
18–23 Oct
4.95 out of 5 average rating, 58 reviews
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Guest favourite
Home in Oakland
Pet Friendly Cozy Home w/Hot Tub & Fire Pit at DCL
1 bedroom, 1 bed
20–25 Sept
4.95 out of 5 average rating, 42 reviews
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Chalet in Oakland
Log chalet w/ hot tub & BBQ grill
5 bedrooms, 8 beds
28 Sept – 3 Oct
4.8 out of 5 average rating, 61 reviews
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Top guest favourite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed
27 Sept – 2 Oct
5.0 out of 5 average rating, 192 reviews
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Top guest favourite
Cabin in Oakland
Romantic Cabin Walk to Lake & Dining/Hot tub/Dog
2 bedrooms, 2 beds
7–12 Dec
5.0 out of 5 average rating, 118 reviews
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Guest favourite
Home in Oakland
The Other House
1 bedroom, 1 bed
27 Sept – 2 Oct
4.92 out of 5 average rating, 26 reviews
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Guest favourite
Cabin in Oakland
Secluded Mtn Cabin: 7BR, Pool, Hot Tub, Game Room
7 bedrooms, 12 beds
20–25 Sept
4.92 out of 5 average rating, 25 reviews
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Top guest favourite
Home in Oakland
Elegant Home Away: Hot Tub/Game Room/Kid-Friendly
4 bedrooms, 9 beds
4–9 Oct
4.91 out of 5 average rating, 54 reviews
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Guest favourite
Cabin in Oakland
Lakehound Lodge - lake view, pet friendly
3 bedrooms, 3 king beds
12–17 Oct
4.92 out of 5 average rating, 271 reviews
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Guest favourite
Cabin in Oakland
C Box MountainTop
2 bedrooms, 3 beds
2–7 Nov
4.9 out of 5 average rating, 60 reviews