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Search results; Over 1,000 homes in Oakland

Top guest favourite
Chalet in Oakland
Happy Our Retreat. Amazing Lake/Mtn Views!
3 bedrooms, 4 beds, 2 private bathrooms
31 Aug – 5 Sept
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4.96 out of 5 average rating, 172 reviews
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
7BR Luxury Log Home, pool, hottub, near Deep Creek
5.0 out of 5 average rating, 17 reviews, 7 bedrooms, 10 beds, 4 bathrooms
20–25 Sept
Top guest favourite
Cabin in Oakland
Romantic Cabin Walk to Lake & Dining/Hot tub/Dogs
5.0 out of 5 average rating, 102 reviews, 2 bedrooms, 2 beds, 1 bathroom
25–30 Oct
Top guest favourite
Yurt in Oakland
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
5.0 out of 5 average rating, 41 reviews, 1 bed, 1 bathroom
12–17 Jul
Top guest favourite
Cabin in Oakland
Speakeasy | Bunk Room | Hot Tub | Private 2 acres
4.98 out of 5 average rating, 41 reviews, 3 bedrooms, 7 beds, 3.5 bathrooms
27 Jul – 1 Aug
Top guest favourite
Home in Oakland
The Other House
5.0 out of 5 average rating, 16 reviews, 1 bedroom, 1 bed, 1 bathroom
5–10 Jul
Top guest favourite
Home in Oakland
Lazy Bear Cabin Deep Creek Lake
4.96 out of 5 average rating, 93 reviews, 2 bedrooms, 2 beds, 2 bathrooms
6–11 Jul
Home in Oakland
Secluded Oakland Gem w/ Hot Tub: Dogs Welcome!
4.88 out of 5 average rating, 52 reviews, 3 bedrooms, 4 beds, 2 bathrooms
7–12 Jul
Top guest favourite
Tiny home in Oakland
Lil' Sumpin
5.0 out of 5 average rating, 81 reviews, 1 bedroom, 1 bed, 1 bathroom
11–16 Jul
Superhost
Home in McHenry
Lake Bear Lair | Formerly Stars & Stripes | HotTub
New place to stay, 4 bedrooms, 8 beds, 4 bathrooms
21–26 Jul
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
Guest favourite
Cottage in Oakland
Pet friendly-Cottage in the Woods
4.9 out of 5 average rating, 242 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Top guest favourite
Home in Oakland
Lake View Loft Lodge on Deep Creek Lake
4.94 out of 5 average rating, 168 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Home in Oakland
Elegant Home Away: Hot Tub/Game Room/Kid-Friendly
4.9 out of 5 average rating, 49 reviews, 4 bedrooms, 9 beds, 3.5 bathrooms
19–24 Jul
Top guest favourite
Home in Oakland
Lake View, Private Beach, Hot Tub, King Beds, Lux
4.95 out of 5 average rating, 64 reviews, 4 bedrooms, 5 beds, 3.5 bathrooms
6–11 Jul
Home in Oakland
Cottage on Jericho Road
4.71 out of 5 average rating, 14 reviews, 3 bedrooms, 3 beds, 1 bathroom
18–23 Jul
Top guest favourite
Home in McHenry
Newly Renovated 2 Bed/2 Bath in Deep Creek
4.95 out of 5 average rating, 385 reviews, 2 bedrooms, 2 beds, 2 bathrooms
12–17 Jul
Top guest favourite
Home in Oakland
Spring is in the air at our Lake View Condo!
4.97 out of 5 average rating, 122 reviews, 3 bedrooms, 4 beds, 2 bathrooms
6–11 Jul