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Search results; Over 1,000 homes in Oakland

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Top guest favourite
Cottage in Oakland
Stone Haven
2 bedrooms, 3 beds, 1 private bathroom
11–16 Sept
,
4.96 out of 5 average rating, 211 reviews
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Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds, 2 bathrooms
14–19 Sept
4.89 out of 5 average rating, 110 reviews
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Top guest favourite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 185 reviews
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Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds, 1 bathroom
6–11 Sept
4.85 out of 5 average rating, 26 reviews
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Flat in Oakland
Large 2-bdrm apt. Walking distance to everything
2 bedrooms, 2 beds, 1 bathroom
28 Dec – 2 Jan
4.82 out of 5 average rating, 84 reviews
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Flat in Oakland
Cozy studio nook, close to everything
1 bedroom, 1 double bed, 1 bathroom
27 Sept – 4 Oct
4.63 out of 5 average rating, 70 reviews
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Guest favourite
Cabin in Oakland
Quiet 2 bdrm cottage w/firepit & trees
2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.9 out of 5 average rating, 87 reviews
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Top guest favourite
Home in Oakland
Elegant Home Away: Hot Tub/Game Room/Kid-Friendly
4 bedrooms, 9 beds, 3.5 bathrooms
7–12 Sept
4.9 out of 5 average rating, 52 reviews
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Top guest favourite
Cabin in Oakland
Dog Friendly Cabin in the Woods, Hot Tub & Firepit
3 bedrooms, 4 beds, 1.5 bathrooms
19–24 Sept
4.97 out of 5 average rating, 34 reviews
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Cabin in Terra Alta
Unique Rustic Cabin w/ Lake Access & Kayak
1 bedroom, 1 king bed, 1 bathroom
5–10 Oct
5.0 out of 5 average rating, 15 reviews
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Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds, 2.5 bathrooms
13–18 Sept
4.98 out of 5 average rating, 166 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, 2 bathrooms
27 Sept – 2 Oct
4.95 out of 5 average rating, 394 reviews
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Superhost
Home in Oakland
LakeShore LoftHouse
2 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.93 out of 5 average rating, 40 reviews
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Home in Oakland
Lainee Jayne's at Deep Creek Lake
4 bedrooms, 5 beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 5 reviews
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Guest favourite
Home in Oakland
The Other House
1 bedroom, 1 bed, 1 bathroom
1–6 Sept
4.91 out of 5 average rating, 23 reviews
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Guest favourite
Chalet in Oakland
Log chalet w/ hot tub & BBQ grill
5 bedrooms, 8 beds, 4 bathrooms
20–25 Sept
4.8 out of 5 average rating, 59 reviews
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Guest favourite
Cabin in Oakland
C Box MountainTop
2 bedrooms, 3 beds, 2 bathrooms
21–26 Sept
4.9 out of 5 average rating, 59 reviews
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Top guest favourite
Cabin in Oakland
Captain's Quarters Deep Creek Log Cabin Oasis
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 119 reviews
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Guest favourite
Cabin in Oakland
Cozy Cabin in the Woods
2 bedrooms, 5 beds, 1.5 bathrooms
11–16 Sept
4.98 out of 5 average rating, 66 reviews