filters

Search results; Over 1,000 homes in Oakland

Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds, 2.5 bathrooms
15–20 Sept
4.98 out of 5 average rating, 170 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds, 2 bathrooms
12–17 Oct
4.88 out of 5 average rating, 112 reviews
Top guest favourite
Home in Oakland
Deep Creek Dome Cabin | Fire Pit & EV Near Wisp
4 bedrooms, 6 beds, 3 bathrooms
18–23 Oct
4.95 out of 5 average rating, 57 reviews
Top guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds, 1 bathroom
4–9 Oct
4.87 out of 5 average rating, 30 reviews
Top guest favourite
Home in Oakland
Elegant Home Away: Hot Tub/Game Room/Kid-Friendly
4 bedrooms, 9 beds, 3.5 bathrooms
4–9 Oct
4.91 out of 5 average rating, 54 reviews
Guest favourite
Home in Oakland
"Das Haus Am See" (the house at the lake)
3 bedrooms, 3 beds, 3 bathrooms
16–21 Sept
5.0 out of 5 average rating, 16 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
Top guest favourite
Home in Oakland
Lucy’s Lookout
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.94 out of 5 average rating, 16 reviews
Top guest favourite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 192 reviews
Superhost
Cabin in Oakland
Incredible Cozy Cabin Immersed in Nature
3 bedrooms, 6 beds, 1 bathroom
28 Sept – 3 Oct
4.84 out of 5 average rating, 459 reviews
Guest favourite
Cabin in Oakland
Cabin near lake, family & pet friendly, hot tub!
3 bedrooms, 5 beds, 3 bathrooms
2–7 Oct
4.92 out of 5 average rating, 97 reviews
Top guest favourite
Home in Oakland
DCL Cottage with MD State Park Pass
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
4.98 out of 5 average rating, 87 reviews
Guest favourite
Cottage in Oakland
Deep Creek Lake Cabin 3BR 1.5BA Honi, Wisp, & More
3 bedrooms, 6 beds, 1.5 bathrooms
16–21 Sept
4.93 out of 5 average rating, 68 reviews
Top guest favourite
Home in McHenry
Newly Renovated 2 Bed/2 Bath in Deep Creek
2 bedrooms, 2 queen beds, 2 bathrooms
27 Sept – 2 Oct
4.95 out of 5 average rating, 397 reviews
Top guest favourite
Cabin in Oakland
Captain's Quarters Deep Creek Log Cabin Oasis
2 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.98 out of 5 average rating, 121 reviews
Guest favourite
Home in Oakland
Private Lodge sleeps 31 guests Spectacular Views
8 bedrooms, 16 beds, 5 bathrooms
12–17 Oct
4.91 out of 5 average rating, 57 reviews
Guest favourite
Home in McHenry
Cozy Lake House with Dock
3 bedrooms, 6 beds, 3 bathrooms
11–16 Oct
4.92 out of 5 average rating, 119 reviews
Top guest favourite
Cabin in Oakland
Dog Friendly Cabin in the Woods, Hot Tub & Firepit
3 bedrooms, 4 beds, 1.5 bathrooms
20–25 Sept
4.97 out of 5 average rating, 34 reviews