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Search results; Over 1,000 homes in Oakland

Top guest favourite
Cabin in Oakland
Dancing Bears
3 bedrooms, 4 beds, 1 private bathroom
1–6 Aug
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4.97 out of 5 average rating, 230 reviews
Top guest favourite
Cabin in Oakland
Oakland Bear Lair | 7BR Luxury Log | Pool, Hot tub
5.0 out of 5 average rating, 19 reviews, 7 bedrooms, 10 beds, 4 bathrooms
20–25 Sept
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
4.9 out of 5 average rating, 106 reviews, 5 bedrooms, 6 beds, 2 bathrooms
17–22 Aug
Top guest favourite
Tiny home in Oakland
The Grist Mill
5.0 out of 5 average rating, 175 reviews, 1 bedroom, 1 bed, 1 bathroom
15–20 Aug
Guest favourite
Home in Oakland
Cottage on Jericho Road
4.8 out of 5 average rating, 20 reviews, 3 bedrooms, 3 beds, 1 bathroom
10–15 Aug
Home in Oakland
Lainee Jayne's at Deep Creek Lake
New place to stay, 4 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
Superhost
Home in McHenry
Lake Bear Lair | Formerly Stars & Stripes | HotTub
New place to stay, 4 bedrooms, 8 beds, 4 bathrooms
16–21 Aug
Guest favourite
Cabin in Terra Alta
Mountain cabin w/ deck & lake access
4.94 out of 5 average rating, 17 reviews, 6 bedrooms, 9 beds, 3.5 bathrooms
23–28 Aug
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
4.98 out of 5 average rating, 162 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
9–14 Aug
Top guest favourite
Cottage in Oakland
Stone Haven
4.96 out of 5 average rating, 208 reviews, 2 bedrooms, 4 beds, 1 bathroom
9–14 Aug
Top guest favourite
Home in Oakland
Deep Creek Dome Cabin | Fire Pit & EV Near Wisp
4.96 out of 5 average rating, 45 reviews, 4 bedrooms, 6 beds, 3 bathrooms
23–28 Aug
Guest favourite
Chalet in Oakland
Log chalet w/ hot tub & BBQ grill
4.87 out of 5 average rating, 53 reviews, 5 bedrooms, 8 beds, 4 bathrooms
23–28 Aug
Top guest favourite
Home in McHenry
Newly Renovated 2 Bed/2 Bath in Deep Creek
4.95 out of 5 average rating, 390 reviews, 2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
Top guest favourite
Cabin in Oakland
Speakeasy | Bunk Room | Hot Tub | Private 2 acres
4.98 out of 5 average rating, 44 reviews, 3 bedrooms, 7 beds, 3.5 bathrooms
23–28 Aug
Top guest favourite
Home in Oakland
7-Bed Lake Retreat w/ Hot Tub & 5 mins to Wisp Ski
4.98 out of 5 average rating, 52 reviews, 4 bedrooms, 7 beds, 4.5 bathrooms
22–27 Aug
Guest favourite
Cabin in Oakland
Deep Creek Aframe : Lake View, Dock slip, Hot Tub
4.91 out of 5 average rating, 69 reviews, 5 bedrooms, 10 beds, 4 bathrooms
22–27 Aug
Top guest favourite
Cabin in Accident
Rustic Luxe Cabin (4x4 Required)
4.98 out of 5 average rating, 94 reviews, 2 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
Top guest favourite
Treehouse in McHenry
Bird's Eye View
4.99 out of 5 average rating, 211 reviews, 1 bedroom, 3 beds, 1 bathroom
12–17 Oct
Guest favourite
Cabin in Oakland
HotTub-FirePit-8MintoWisp-Arcade-N64-NoCleaningFee
4.99 out of 5 average rating, 202 reviews, 4 bedrooms, 9 beds, 2.5 bathrooms
23–28 Aug