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Search results; Over 1,000 homes in Oakland

Guest favourite
Home in Oakland
Beautiful LAKE VIEW w/HOT TUB, Fire Pit & GameRoom
4 bedrooms, 6 beds, 2.5 private bathrooms
4–9 Oct
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4.84 out of 5 average rating, 193 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds
14–19 Sept
4.89 out of 5 average rating, 110 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
Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds
6–11 Sept
4.85 out of 5 average rating, 26 reviews
Top guest favourite
Home in Oakland
Elegant Home Away: Hot Tub/Game Room/Kid-Friendly
4 bedrooms, 9 beds
7–12 Sept
4.9 out of 5 average rating, 52 reviews
Superhost
Home in Oakland
Private Lodge sleeps 31 guests Spectacular Views
8 bedrooms, 16 beds
13–18 Sept
4.91 out of 5 average rating, 53 reviews
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds
13–18 Sept
4.98 out of 5 average rating, 166 reviews
Guest favourite
Cabin in Oakland
Oakland Bear Lair|7BR Luxury Log|Pool, Hot tub
7 bedrooms, 12 beds
20–25 Sept
4.91 out of 5 average rating, 23 reviews
Guest favourite
Cabin in Oakland
Quiet 2 bdrm cottage w/firepit & trees
2 bedrooms, 4 beds
20–25 Sept
4.9 out of 5 average rating, 87 reviews
Top guest favourite
Cabin in Oakland
Speakeasy | Bunk Room | Hot Tub | Private 2 acres
3 bedrooms, 7 beds
7–12 Sept
4.98 out of 5 average rating, 49 reviews
Superhost
Cabin in Oakland
2 great cabins - 1 special memory
5 bedrooms, 9 beds
13–18 Sept
Guest favourite
Cabin in Oakland
Pool, HotTub, FirePit, EVCharger, & Great Location
6 bedrooms, 10 beds
1–6 Sept
4.98 out of 5 average rating, 126 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, 393 reviews
Guest favourite
Home in Oakland
Lucy’s Lookout
3 bedrooms, 4 beds
3–8 Sept
4.92 out of 5 average rating, 13 reviews
Top guest favourite
Home in Oakland
DCL Cottage with MD State Park Pass
3 bedrooms, 4 beds
1–6 Sept
4.98 out of 5 average rating, 85 reviews
Top guest favourite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed
13–18 Sept
5.0 out of 5 average rating, 185 reviews
Top guest favourite
Cabin in Oakland
Cozy Cabin w/ Hot Tub/Game Room – near Deep Creek!
3 bedrooms, 3 queen beds
1–6 Sept
5.0 out of 5 average rating, 82 reviews
Guest favourite
Townhouse in Oakland
Lake View Condo with Grill and Wood Fireplace!
2 bedrooms, 5 beds
13–18 Sept
4.9 out of 5 average rating, 274 reviews
Guest favourite
Cabin in Oakland
Cabin near lake, family & pet friendly, hot tub!
3 bedrooms, 5 beds
7–12 Sept
4.91 out of 5 average rating, 93 reviews