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
26–31 Aug
,
4.96 out of 5 average rating, 171 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
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
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
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds, 2 bathrooms
10–15 Aug
4.89 out of 5 average rating, 104 reviews
Top guest favourite
Yurt in Oakland
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
1 king bed, 1 bathroom
6–11 Jul
5.0 out of 5 average rating, 41 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, 101 reviews
Guest favourite
Cabin in Oakland
Cozy Cabin in the Woods
2 bedrooms, 5 beds, 1.5 bathrooms
12–17 Jul
4.98 out of 5 average rating, 63 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
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
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
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
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
Cabin in Aurora
Whispering Pines: Cabin in woods near Thomas/Davis
2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 4 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
Guest favourite
Camper van/Motorhome in Oakland
A quaint camper minutes from Deep Creek Lake
1 bedroom, 3 beds, 1 bathroom
5–10 Jul
4.93 out of 5 average rating, 14 reviews
Superhost
Home in McHenry
Lake View | Hot Tub Pool Gym & Games | EV Charger
4 bedrooms, 5 beds, 3.5 bathrooms
7–12 Jul
New place to stay
Top guest favourite
Tiny home in Oakland
Lil' Sumpin
1 bedroom, 1 double bed, 1 bathroom
11–16 Jul
5.0 out of 5 average rating, 81 reviews