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Search results; Over 1,000 homes in Oakland

Top guest favourite
Cabin in Oakland
Dancing Bears
3 bedrooms, 4 beds, 1 private bathroom
14–19 Sept
,
4.97 out of 5 average rating, 231 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds
28 Sept – 3 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
Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds
27 Sept – 2 Oct
4.86 out of 5 average rating, 28 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, 169 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, 189 reviews
Guest favourite
Home in Oakland
Deep Creek Dome Cabin | Fire Pit & EV Near Wisp
4 bedrooms, 6 beds
4–9 Oct
4.95 out of 5 average rating, 56 reviews
Guest favourite
Home in Oakland
Private Lodge sleeps 31 guests Spectacular Views
8 bedrooms, 16 beds
13–18 Sept
4.91 out of 5 average rating, 56 reviews
Guest favourite
Cabin in Terra Alta
Secluded Mountain Lake Escape w/ Dock & Kayaks
4 bedrooms, 4 beds
20–25 Sept
4.89 out of 5 average rating, 54 reviews
Flat in Oakland
Cozy studio nook, close to everything
1 bedroom, 1 double bed
27 Sept – 4 Oct
4.63 out of 5 average rating, 70 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
Superhost
Cabin in Oakland
Incredible Cozy Cabin Immersed in Nature
3 bedrooms, 6 beds
13–18 Sept
4.84 out of 5 average rating, 459 reviews
Top guest favourite
Cabin in Oakland
Captain's Quarters Deep Creek Log Cabin Oasis
2 bedrooms, 3 beds
11–16 Sept
4.98 out of 5 average rating, 121 reviews
Top guest favourite
Cabin in Oakland
Romantic Cabin Walk to Lake & Dining/Hot tub/Dog
2 bedrooms, 2 beds
30 Oct – 4 Nov
5.0 out of 5 average rating, 117 reviews
Superhost
Home in Friendsville
12 bd, 9 Bath, 14 acres, pool, Waterfront, Events!
12 bedrooms, 25 beds
10–15 Sept
New place to stay
Guest favourite
Camper van/Motorhome in Oakland
A quaint camper minutes from Deep Creek Lake
1 bedroom, 3 beds
17–22 Sept
4.89 out of 5 average rating, 19 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
Holiday home in Oakland
Lakefront Cabin in Stunning Storybook Setting
3 bedrooms, 6 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 145 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