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Search results; Over 1,000 homes in Oakland

Guest favourite
Home in Oakland
Spacious Home Near All Deep Creek MD Has to Offer
4 bedrooms, 6 beds, 3 private bathrooms
12–17 Jul
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4.9 out of 5 average rating, 108 reviews
Top guest favourite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 169 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds, 2 bathrooms
13–18 Jul
4.89 out of 5 average rating, 104 reviews
Top guest favourite
Home in Oakland
The Other House
1 bedroom, 1 bed, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Cabin in Oakland
Romantic Cabin Walk to Lake & Dining/Hot tub/Dogs
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 100 reviews
Top guest favourite
Cabin in Oakland
HotTub-FirePit-8MintoWisp-Arcade-N64-NoCleaningFee
4 bedrooms, 9 beds, 2.5 bathrooms
5–10 Jul
4.99 out of 5 average rating, 198 reviews
Top guest favourite
Home in Oakland
Elegant Home Away: Hot Tub/Game Room/Kid-Friendly
4 bedrooms, 9 beds, 3.5 bathrooms
19–24 Jul
4.9 out of 5 average rating, 49 reviews
Superhost
Loft in Oakland
One bedroom Loft-15 from WISP & close to Walmart
1 bedroom, 1 queen bed, 1 bathroom
4–9 Jul
4.73 out of 5 average rating, 86 reviews
Guest favourite
Home in Oakland
"Das Haus Am See" (the house at the lake)
3 bedrooms, 3 beds, 3 bathrooms
25–30 Jul
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Cabin in Oakland
Speakeasy | Bunk Room | Hot Tub | Private 2 acres
3 bedrooms, 7 beds, 3.5 bathrooms
27 Jul – 1 Aug
4.98 out of 5 average rating, 41 reviews
Top guest favourite
Home in Oakland
Lazy Bear Cabin Deep Creek Lake
2 bedrooms, 2 queen beds, 2 bathrooms
6–11 Jul
4.96 out of 5 average rating, 92 reviews
Home in Oakland
Secluded Oakland Gem w/ Hot Tub: Dogs Welcome!
3 bedrooms, 4 beds, 2 bathrooms
7–12 Jul
4.88 out of 5 average rating, 51 reviews
Top guest favourite
Home in Oakland
7-Bed Lake Retreat w/ Hot Tub & 5 mins to Wisp Ski
4 bedrooms, 7 beds, 4.5 bathrooms
22–27 Aug
5.0 out of 5 average rating, 47 reviews
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds, 2.5 bathrooms
12–17 Jul
4.98 out of 5 average rating, 157 reviews
Top guest favourite
Home in McHenry
Newly Renovated 2 Bed/2 Bath in Deep Creek
2 bedrooms, 2 queen beds, 2 bathrooms
12–17 Jul
4.95 out of 5 average rating, 384 reviews
Top guest favourite
Cabin in Oakland
Luxury 7BR Cabin|HotTub|HeatedPool
7 bedrooms, 10 beds, 4 bathrooms
13–18 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Home in Oakland
Historic 6BR Family Getaway
6 bedrooms, 7 beds, 2.5 bathrooms
21–26 Jul
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Yurt in Oakland
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
1 king bed, 1 bathroom
3–8 Jul
5.0 out of 5 average rating, 41 reviews
Guest favourite
Cabin in Oakland
Cabin near lake, family & pet friendly, hot tub!
3 bedrooms, 5 beds, 3 bathrooms
6–11 Jul
4.92 out of 5 average rating, 85 reviews