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Search results; Over 1,000 homes in Oakland

Guest favourite
Chalet in Oakland
Spectacular Chalet, Timroc II, close to lake, Wisp
5 bedrooms, 9 beds, 3.5 private bathrooms
22–27 Aug
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4.92 out of 5 average rating, 138 reviews
Top guest favourite
Tiny home in Oakland
The Grist Mill
5.0 out of 5 average rating, 171 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Jul
Guest favourite
Home in Oakland
The Other House
4.94 out of 5 average rating, 17 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Flat in Oakland
Large 2-bdrm apt. Walking distance to everything
4.82 out of 5 average rating, 84 reviews, 2 bedrooms, 2 beds, 1 bathroom
28 Nov – 3 Dec
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
4.89 out of 5 average rating, 104 reviews, 5 bedrooms, 6 beds, 2 bathrooms
10–15 Aug
Top guest favourite
Cabin in Oakland
Dog Friendly Cabin in the Woods, Hot Tub & Firepit
4.97 out of 5 average rating, 33 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
19–24 Jul
Loft in Oakland
One bedroom Loft-15 from WISP & close to Walmart
4.73 out of 5 average rating, 88 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Guest favourite
Home in Oakland
"Das Haus Am See" (the house at the lake)
5.0 out of 5 average rating, 15 reviews, 3 bedrooms, 3 beds, 3 bathrooms
14–19 Jul
Top guest favourite
Cabin in McHenry
Spacious 5BR Family Cabin
5.0 out of 5 average rating, 55 reviews, 5 bedrooms, 8 beds, 5.5 bathrooms
12–17 Jul
Top guest favourite
Cabin in Oakland
Romantic Cabin Walk to Lake & Dining/Hot tub/Dogs
5.0 out of 5 average rating, 103 reviews, 2 bedrooms, 2 beds, 1 bathroom
25–30 Oct
Top guest favourite
Cottage in Oakland
Stone Haven
4.96 out of 5 average rating, 205 reviews, 2 bedrooms, 4 beds, 1 bathroom
28 Jul – 2 Aug
Top guest favourite
Chalet in Oakland
The Dacha - Lake Views, Hot Tub, minutes from Wisp
4.99 out of 5 average rating, 157 reviews, 3 bedrooms, 4 beds, 3 bathrooms
12–17 Jul
Top guest favourite
Cabin in Oakland
Cozy Cabin w/ Hot Tub/Game Room – near Deep Creek!
5.0 out of 5 average rating, 80 reviews, 3 bedrooms, 3 beds, 2 bathrooms
4–9 Aug
Guest favourite
Home in Oakland
Cottage on Jericho Road
4.75 out of 5 average rating, 16 reviews, 3 bedrooms, 3 beds, 1 bathroom
18–23 Jul
Top guest favourite
Cabin in Oakland
Speakeasy | Bunk Room | Hot Tub | Private 2 acres
4.98 out of 5 average rating, 42 reviews, 3 bedrooms, 7 beds, 3.5 bathrooms
27 Jul – 1 Aug
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
4.98 out of 5 average rating, 159 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
12–17 Jul
Guest favourite
Home in Oakland
Historic 6BR Family Getaway
5.0 out of 5 average rating, 6 reviews, 6 bedrooms, 7 beds, 2.5 bathrooms
21–26 Jul
Top guest favourite
Cabin in Oakland
SUGARBUSH - Sweet Serenity Tiny House
4.98 out of 5 average rating, 179 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
Guest favourite
Camper van/Motorhome in Oakland
A quaint camper minutes from Deep Creek Lake
4.93 out of 5 average rating, 14 reviews, 1 bedroom, 3 beds, 1 bathroom
12–17 Jul