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Search results; Over 1,000 homes in Oakland

Cottage in Oakland
Scenic Deep Creek Getaway Cabin- RICKY'S RETREAT
4 bedrooms, 8 beds, 2 private bathrooms
16–21 Sept
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4.52 out of 5 average rating, 87 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds
12–17 Oct
4.88 out of 5 average rating, 112 reviews
Flat in Oakland
Large 2-bdrm apt. Walking distance to everything
2 bedrooms, 2 beds
28 Dec – 2 Jan
4.82 out of 5 average rating, 84 reviews
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds
14–19 Sept
4.98 out of 5 average rating, 170 reviews
Top guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds
4–9 Oct
4.86 out of 5 average rating, 29 reviews
Top guest favourite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed
14–19 Sept
5.0 out of 5 average rating, 189 reviews
Top guest favourite
Home in Oakland
Deep Creek Dome Cabin | Fire Pit & EV Near Wisp
4 bedrooms, 6 beds
18–23 Oct
4.95 out of 5 average rating, 57 reviews
Guest favourite
Home in Oakland
"Das Haus Am See" (the house at the lake)
3 bedrooms, 3 beds
15–20 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in McHenry
Newly Renovated 2 Bed/2 Bath in Deep Creek
2 bedrooms, 2 queen beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 397 reviews
Top guest favourite
Home in Oakland
Elegant Home Away: Hot Tub/Game Room/Kid-Friendly
4 bedrooms, 9 beds
4–9 Oct
4.91 out of 5 average rating, 54 reviews
Guest favourite
Home in Oakland
The Other House
1 bedroom, 1 bed
14–19 Sept
4.92 out of 5 average rating, 25 reviews
Guest favourite
Home in Oakland
Private Lodge sleeps 31 guests Spectacular Views
8 bedrooms, 16 beds
17–22 Oct
4.91 out of 5 average rating, 56 reviews
Top guest favourite
Home in Oakland
Broadford Park View
5 bedrooms, 8 beds
21–26 Sept
4.95 out of 5 average rating, 42 reviews
Top guest favourite
Home in Oakland
DCL Cottage with MD State Park Pass
3 bedrooms, 4 beds
20–25 Sept
4.98 out of 5 average rating, 87 reviews
Guest favourite
Home in McHenry
Cozy Lake House with Dock
3 bedrooms, 6 beds
11–16 Oct
4.92 out of 5 average rating, 119 reviews
Top guest favourite
Home in Oakland
Lucy’s Lookout
3 bedrooms, 4 beds
20–25 Sept
4.94 out of 5 average rating, 16 reviews
Guest favourite
Chalet in Oakland
Private (5 Star!) Lake Access Chalet w/ Hot Tub
3 bedrooms, 5 beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 373 reviews
Guest favourite
Cabin in Oakland
Secluded Mtn Cabin: 7BR, Pool, Hot Tub, Game Room
7 bedrooms, 12 beds
20–25 Sept
4.92 out of 5 average rating, 25 reviews
Top guest favourite
Cabin in Oakland
Dog Friendly Cabin in the Woods, Hot Tub & Firepit
3 bedrooms, 4 beds
20–25 Sept
4.97 out of 5 average rating, 34 reviews