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Search results; Over 1,000 homes in Oakland

Guest favourite
Chalet in Oakland
Lakefront A-Frame | Hot Tub, Private Dock, Views
5 bedrooms, 7 beds, 3 private bathrooms
30 Aug – 4 Sept
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5.0 out of 5 average rating, 16 reviews
Top guest favourite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 181 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds, 2 bathrooms
20–25 Aug
4.89 out of 5 average rating, 109 reviews
Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds, 1 bathroom
23–28 Aug
4.84 out of 5 average rating, 25 reviews
Guest favourite
Cabin in Oakland
Oakland Bear Lair|7BR Luxury Log|Pool, Hot tub
7 bedrooms, 12 beds, 4 bathrooms
20–25 Sept
4.95 out of 5 average rating, 21 reviews
Top guest favourite
Cabin in Oakland
Captain's Quarters Deep Creek Log Cabin Oasis
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 116 reviews
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds, 2.5 bathrooms
19–24 Aug
4.98 out of 5 average rating, 166 reviews
Guest favourite
Cabin in Oakland
Dar's Deep Creek Timber Hideaway
3 bedrooms, 6 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 6 reviews
Home in Oakland
Lainee Jayne's at Deep Creek Lake
4 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Oakland
Big Boulder Retreat! - at Deep Creek Lake
2 bedrooms, 3 beds, 1 bathroom
19–24 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Cabin in Oakland
Romantic Cabin Walk to Lake & Dining/Hot tub/Dog
2 bedrooms, 2 beds, 1 bathroom
30 Oct – 4 Nov
5.0 out of 5 average rating, 113 reviews
Superhost
Cabin in Oakland
2 great cabins - 1 special memory
5 bedrooms, 9 beds, 3 bathrooms
30 Aug – 4 Sept
Top guest favourite
Cabin in Oakland
Speakeasy | Bunk Room | Hot Tub | Private 2 acres
3 bedrooms, 7 beds, 3.5 bathrooms
7–12 Sept
4.98 out of 5 average rating, 46 reviews
Guest favourite
Home in Oakland
The Other House
1 bedroom, 1 bed, 1 bathroom
24–29 Aug
4.95 out of 5 average rating, 21 reviews
Top guest favourite
Cabin in Aurora
Whispering Pines: Cabin in woods near Thomas/Davis
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Oakland
Deep Creek Dome Cabin | Fire Pit & EV Near Wisp
4 bedrooms, 6 beds, 3 bathrooms
4–9 Oct
4.94 out of 5 average rating, 53 reviews
Top guest favourite
Home in Oakland
The Barn @ Silo Farm | Deep Creek Lake, MD
2 bedrooms, 4 beds, 1.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 57 reviews
Superhost
Home in McHenry
Pet-Friendly Cabin w HotTub/FirePit. Close to WISP
5 bedrooms, 9 beds, 3 bathrooms
23–28 Aug
New place to stay
Top guest favourite
Chalet in Oakland
The Dacha - Cozy with Lake Views, Hot Tub,
3 bedrooms, 4 beds, 3 bathrooms
23–28 Aug
4.98 out of 5 average rating, 160 reviews