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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
13–18 Sept
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4.85 out of 5 average rating, 198 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
13–18 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
Top guest favourite
Cabin in Oakland
Dar's Deep Creek Timber Hideaway
3 bedrooms, 6 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Cabin in Oakland
Cabin near lake, family & pet friendly, hot tub!
3 bedrooms, 5 beds, 3 bathrooms
21–26 Sept
4.92 out of 5 average rating, 95 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, 117 reviews
Guest favourite
Home in Oakland
Private Lodge sleeps 31 guests Spectacular Views
8 bedrooms, 16 beds, 5 bathrooms
13–18 Sept
4.91 out of 5 average rating, 55 reviews
Guest favourite
Home in McHenry
Cozy Lake House with Dock
3 bedrooms, 6 beds, 3 bathrooms
11–16 Oct
4.92 out of 5 average rating, 119 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
Cabin in Oakland
Captain's Quarters Deep Creek Log Cabin Oasis
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 120 reviews
Guest favourite
Chalet in Oakland
Private (5 Star!) Lake Access Chalet w/ Hot Tub
3 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
4.95 out of 5 average rating, 371 reviews
Superhost
Cottage in Oakland
Pet friendly-Cottage in the Woods
2 bedrooms, 3 beds, 1 bathroom
10–15 Oct
4.88 out of 5 average rating, 252 reviews
Top guest favourite
Home in Oakland
Lucy’s Lookout
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.93 out of 5 average rating, 15 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
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 186 reviews
Superhost
Cabin in Oakland
Incredible Cozy Cabin Immersed in Nature
3 bedrooms, 6 beds, 1 bathroom
7–12 Sept
4.84 out of 5 average rating, 458 reviews
Guest favourite
Cabin in Oakland
Oakland Bear Lair | 7BR | Pool+Hot Tub + Game Room
7 bedrooms, 12 beds, 4 bathrooms
20–25 Sept
4.92 out of 5 average rating, 24 reviews