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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
Top guest favourite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed, 1 bathroom
26–31 Jul
5.0 out of 5 average rating, 171 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
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
Oakland Bear Lair-7BR, pool, hot-tub, Deep Creek
7 bedrooms, 10 beds, 4 bathrooms
20–25 Sept
5.0 out of 5 average rating, 18 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
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
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
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, 159 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
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
Cabin in Oakland
Cozy Cabin w/ Hot Tub/Game Room – near Deep Creek!
3 bedrooms, 3 queen beds, 2 bathrooms
4–9 Aug
5.0 out of 5 average rating, 80 reviews
Superhost
Cabin in Oakland
Dar's Deep Creek Timber Hideaway
3 bedrooms, 6 beds, 2 bathrooms
18–23 Jul
Guest favourite
Cabin in Oakland
Cozy Cabin in the Woods
2 bedrooms, 5 beds, 1.5 bathrooms
12–17 Jul
4.98 out of 5 average rating, 63 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
Cabin in Oakland
Dog Friendly Cabin in the Woods, Hot Tub & Firepit
3 bedrooms, 4 beds, 1.5 bathrooms
19–24 Jul
4.97 out of 5 average rating, 33 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
Superhost
Home in Oakland
Pet-Friendly, Hot Tub, Beautiful Mountain Cabin
3 bedrooms, 7 beds, 1 bathroom
18–23 Jul
4.89 out of 5 average rating, 9 reviews
Top guest favourite
Treehouse in McHenry
Bird's Eye View
1 bedroom, 3 beds, 1 bathroom
12–17 Oct
4.99 out of 5 average rating, 207 reviews