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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
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4.98 out of 5 average rating, 127 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds, 2 bathrooms
28 Sept – 3 Oct
4.88 out of 5 average rating, 111 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
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
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, 167 reviews
Superhost
Cottage in Oakland
Pet friendly-Cottage in the Woods
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.88 out of 5 average rating, 251 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, 185 reviews
Top guest favourite
Cabin in Oakland
Cozy Cabin w/ Hot Tub/Game Room – near Deep Creek!
3 bedrooms, 3 queen beds, 2 bathrooms
26–31 Oct
5.0 out of 5 average rating, 83 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, 24 reviews
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
4.91 out of 5 average rating, 54 reviews
Top guest favourite
Home in Oakland
Deep Creek Dome Cabin | Fire Pit & EV Near Wisp
4 bedrooms, 6 beds, 3 bathrooms
28 Sept – 3 Oct
4.94 out of 5 average rating, 54 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
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, 395 reviews
Cabin in Oakland
Rustic Swallow Falls Cabin 2
1 bedroom, 2 beds, 1 bathroom
3–8 Sept
New place to stay
Top guest favourite
Home in Swanton
Almost Heaven
4 bedrooms, 7 beds, 3 bathrooms
12–17 Oct
5.0 out of 5 average rating, 34 reviews
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
Guest favourite
Cabin in Oakland
SUGARBUSH - Sweet Serenity Tiny House
1 bedroom, 1 queen bed, 1 bathroom
7–12 Sept
4.98 out of 5 average rating, 180 reviews
Top guest favourite
Townhouse in McHenry
Our Lovely Lake Retreat
3 bedrooms, 4 beds, 2.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 109 reviews
Home in Swanton
Deep Creek Lake, Wisp, Dog Friendly
3 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
4.86 out of 5 average rating, 85 reviews