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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, 198 reviews
Guest favourite
Cabin in Oakland
Oakland Bear Lair | 7BR Luxury Log | Pool, Hot tub
7 bedrooms, 10 beds, 4 bathrooms
20–25 Sept
4.95 out of 5 average rating, 20 reviews
Top guest favourite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed, 1 bathroom
15–20 Aug
5.0 out of 5 average rating, 177 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds, 2 bathrooms
9–14 Aug
4.89 out of 5 average rating, 107 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
10–15 Aug
4.8 out of 5 average rating, 20 reviews
Superhost
Cabin in Oakland
2 great cabins - 1 special memory
5 bedrooms, 9 beds, 3 bathrooms
30 Aug – 4 Sept
Top guest favourite
Cottage in Oakland
Stone Haven
2 bedrooms, 4 beds, 1 bathroom
9–14 Aug
4.96 out of 5 average rating, 208 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, 114 reviews
Top guest favourite
Home in McHenry
Newly Renovated 2 Bed/2 Bath in Deep Creek
2 bedrooms, 2 queen beds, 2 bathrooms
16–21 Aug
4.95 out of 5 average rating, 390 reviews
Top guest favourite
Cabin in Oakland
Speakeasy | Bunk Room | Hot Tub | Private 2 acres
3 bedrooms, 7 beds, 3.5 bathrooms
23–28 Aug
4.98 out of 5 average rating, 44 reviews
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds, 2.5 bathrooms
9–14 Aug
4.98 out of 5 average rating, 162 reviews
Top guest favourite
Cabin in Accident
Rustic Luxe Cabin (4x4 Required)
2 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
4.98 out of 5 average rating, 94 reviews
Superhost
Home in McHenry
Lake Bear Lair | Formerly Stars & Stripes | HotTub
4 bedrooms, 8 beds, 4 bathrooms
10–15 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Oakland
LakeShore LoftHouse
2 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
4.92 out of 5 average rating, 38 reviews
Guest favourite
Chalet in Oakland
Log chalet w/ hot tub & BBQ grill
5 bedrooms, 8 beds, 4 bathrooms
23–28 Aug
4.83 out of 5 average rating, 54 reviews
Guest favourite
Cabin in Oakland
Cabin near lake, family & pet friendly, hot tub!
3 bedrooms, 5 beds, 3 bathrooms
16–21 Aug
4.92 out of 5 average rating, 90 reviews
Guest favourite
Cabin in McHenry
Mad Men Lake House*LAKEFRONT*Fam&Dog Friendly*OUTD
6 bedrooms, 9 beds, 4 bathrooms
29 Aug – 3 Sept
4.96 out of 5 average rating, 165 reviews
Guest favourite
Cabin in Oakland
Quiet 2 bdrm cottage w/firepit & trees
2 bedrooms, 4 beds, 1 bathroom
23–28 Aug
4.9 out of 5 average rating, 84 reviews