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Search results; Over 1,000 homes in Oakland

Guest favourite
Cabin in Oakland
Mountain Escape - Hot Tub, Game Room, Fire Pit
3 bedrooms, 5 beds, 2.5 private bathrooms
23–28 Aug
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4.85 out of 5 average rating, 197 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds, 2 bathrooms
10–15 Aug
4.89 out of 5 average rating, 104 reviews
Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds, 1 bathroom
18–23 Jul
4.75 out of 5 average rating, 16 reviews
Top guest favourite
Cottage in Oakland
Stone Haven
2 bedrooms, 4 beds, 1 bathroom
28 Jul – 2 Aug
4.96 out of 5 average rating, 205 reviews
Top guest favourite
Cabin in Oakland
Romantic Cabin Walk to Lake & Dining/Hot tub/Dogs
2 bedrooms, 2 beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 103 reviews
Guest favourite
Home in Oakland
Historic 6BR Family Getaway
6 bedrooms, 7 beds, 2.5 bathrooms
21–26 Jul
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Oakland
Deep Creek Dome Cabin | Fire Pit & EV Near Wisp
4 bedrooms, 6 beds, 3 bathrooms
23–28 Aug
4.95 out of 5 average rating, 42 reviews
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds, 2.5 bathrooms
12–17 Jul
4.98 out of 5 average rating, 158 reviews
Guest favourite
Home in Oakland
The Other House
1 bedroom, 1 bed, 1 bathroom
12–17 Jul
4.94 out of 5 average rating, 17 reviews
Guest favourite
Home in Oakland
Lake View Loft Lodge on Deep Creek Lake
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.94 out of 5 average rating, 168 reviews
Top guest favourite
Cabin in Terra Alta
Peaceful Cabin w/ Private Dock & Kayaks
4 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
4.95 out of 5 average rating, 40 reviews
Superhost
Cabin in Oakland
Incredible Cozy Cabin Immersed in Nature
3 bedrooms, 6 beds, 1 bathroom
12–17 Jul
4.85 out of 5 average rating, 447 reviews
Guest favourite
Home in Oakland
"Das Haus Am See" (the house at the lake)
3 bedrooms, 3 beds, 3 bathrooms
14–19 Jul
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Cabin in Oakland
C Box MountainTop
2 bedrooms, 3 beds, 2 bathrooms
29 Aug – 3 Sept
4.94 out of 5 average rating, 52 reviews
Top guest favourite
Home in McHenry
Newly Renovated 2 Bed/2 Bath in Deep Creek
2 bedrooms, 2 queen beds, 2 bathrooms
24–29 Aug
4.95 out of 5 average rating, 386 reviews
Top guest favourite
Home in Oakland
7-Bed Lake Retreat w/ Hot Tub & 5 mins to Wisp Ski
4 bedrooms, 7 beds, 4.5 bathrooms
22–27 Aug
5.0 out of 5 average rating, 48 reviews
Top guest favourite
Cabin in Oakland
Speakeasy | Bunk Room | Hot Tub | Private 2 acres
3 bedrooms, 7 beds, 3.5 bathrooms
27 Jul – 1 Aug
4.98 out of 5 average rating, 42 reviews
Guest favourite
Cabin in Oakland
Lakehound Lodge - lake view, pet friendly
3 bedrooms, 3 king beds, 3 bathrooms
1–6 Aug
4.92 out of 5 average rating, 264 reviews
Home in Oakland
Secluded Oakland Gem w/ Hot Tub: Dogs Welcome!
3 bedrooms, 4 beds, 2 bathrooms
12–17 Jul
4.88 out of 5 average rating, 52 reviews