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Search results; Over 1,000 homes in Oakland

Guest favourite
Cabin in Oakland
Pool, HotTub, FirePit, EVCharger, & Great Location
6 bedrooms, 10 beds, 4.5 private bathrooms
13–18 Sept
,
4.98 out of 5 average rating, 128 reviews
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
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, 189 reviews
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
Guest favourite
Home in Oakland
"Das Haus Am See" (the house at the lake)
3 bedrooms, 3 beds, 3 bathrooms
15–20 Sept
5.0 out of 5 average rating, 16 reviews
Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds, 1 bathroom
4–9 Oct
4.86 out of 5 average rating, 29 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds, 2 bathrooms
12–17 Oct
4.88 out of 5 average rating, 112 reviews
Top guest favourite
Home in Oakland
Elegant Home Away: Hot Tub/Game Room/Kid-Friendly
4 bedrooms, 9 beds, 3.5 bathrooms
13–18 Sept
4.91 out of 5 average rating, 54 reviews
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, 169 reviews
Guest favourite
Home in Oakland
The Other House
1 bedroom, 1 bed, 1 bathroom
14–19 Sept
4.92 out of 5 average rating, 25 reviews
Guest favourite
Home in Oakland
General Kelly Guesthouse
5 bedrooms, 6 beds, 2 bathrooms
14–19 Sept
4.83 out of 5 average rating, 167 reviews
Loft in Oakland
One bedroom Loft-15 from WISP & close to Walmart
1 bedroom, 1 queen bed, 1 bathroom
30 Sept – 5 Oct
4.74 out of 5 average rating, 91 reviews
Guest favourite
Cabin in Oakland
Cozy Cabin in the Woods
2 bedrooms, 5 beds, 1.5 bathrooms
20–25 Sept
4.99 out of 5 average rating, 67 reviews
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, 88 reviews
Guest favourite
Home in Oakland
Kestrel's Keeps
4 bedrooms, 4 beds, 3 bathrooms
13–18 Sept
4.95 out of 5 average rating, 87 reviews
Top guest favourite
Cabin in Oakland
Dog Friendly Cabin in the Woods, Hot Tub & Firepit
3 bedrooms, 4 beds, 1.5 bathrooms
20–25 Sept
4.97 out of 5 average rating, 34 reviews
Top guest favourite
Cabin in Oakland
Speakeasy | Bunk Room | Hot Tub | Private 2 acres
3 bedrooms, 7 beds, 3.5 bathrooms
14–19 Sept
4.98 out of 5 average rating, 50 reviews
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, 397 reviews
Top guest favourite
Home in Oakland
Deep Creek Dome Cabin | Fire Pit & EV Near Wisp
4 bedrooms, 6 beds, 3 bathrooms
18–23 Oct
4.95 out of 5 average rating, 57 reviews