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Search results; Over 1,000 homes in Oakland

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Top guest favourite
Cabin in Oakland
HotTub-FirePit-8MintoWisp-Arcade-N64-NoCleaningFee
4 bedrooms, 9 beds, 2.5 private bathrooms
4–9 Oct
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4.99 out of 5 average rating, 208 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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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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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 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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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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Top guest favourite
Cabin in Oakland
Captain's Quarters Deep Creek Log Cabin Oasis
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 122 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 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
Cabin in Oakland
Dog Friendly Cabin in the Woods, Hot Tub & Firepit
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 34 reviews
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Top guest favourite
Tiny home in Oakland
The Original Hob
1 bedroom, 1 queen bed
21–26 Sept
4.98 out of 5 average rating, 206 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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Home in McHenry
Holiday Chalet
3 bedrooms, 3 beds
21–26 Sept
New place to stay
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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
Cabin near lake, family & pet friendly, hot tub!
3 bedrooms, 5 beds
11–16 Oct
4.92 out of 5 average rating, 97 reviews
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Guest favourite
Home in Oakland
General Kelly Guesthouse
5 bedrooms, 6 beds
28 Sept – 3 Oct
4.83 out of 5 average rating, 168 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
Broadford Park View
5 bedrooms, 8 beds
20–25 Oct
4.95 out of 5 average rating, 42 reviews
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Guest favourite
Cabin in Oakland
Quiet 2 bdrm cottage w/firepit & trees
2 bedrooms, 4 beds
20–25 Sept
4.9 out of 5 average rating, 89 reviews