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Search results; Over 1,000 homes in Oakland

Guest favourite
Chalet in Oakland
Central Lake Area, Family Friendly - Dogs welcome!
3 bedrooms, 5 beds, 2.5 private bathrooms
20–25 Sept
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4.95 out of 5 average rating, 87 reviews
Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds
18–23 Jul
4.75 out of 5 average rating, 16 reviews
Top guest favourite
Cabin in Oakland
Romantic Cabin Walk to Lake & Dining/Hot tub/Dogs
2 bedrooms, 2 beds
25–30 Oct
5.0 out of 5 average rating, 104 reviews
Top guest favourite
Cabin in Oakland
Captain's Quarters Deep Creek Log Cabin Oasis
2 bedrooms, 3 beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 110 reviews
Guest favourite
Home in Oakland
The Other House
1 bedroom, 1 bed
19–24 Jul
4.94 out of 5 average rating, 17 reviews
Top guest favourite
Cabin in Oakland
Oakland Bear Lair | 7BR Luxury Log | Pool, Hot tub
7 bedrooms, 10 beds
20–25 Sept
5.0 out of 5 average rating, 18 reviews
Superhost
Cabin in Oakland
Dar's Deep Creek Timber Hideaway
3 bedrooms, 6 beds
18–23 Jul
Home in Oakland
New! Lake Area Home w/ Hot Tub
4 bedrooms, 4 beds
17–22 Jul
New place to stay
Top guest favourite
Cottage in Oakland
Stone Haven
2 bedrooms, 4 beds
9–14 Aug
4.96 out of 5 average rating, 207 reviews
Top guest favourite
Home in Oakland
Deep Creek Dome Cabin | Fire Pit & EV Near Wisp
4 bedrooms, 6 beds
23–28 Aug
4.95 out of 5 average rating, 44 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds
10–15 Aug
4.89 out of 5 average rating, 104 reviews
Top guest favourite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed
26–31 Jul
5.0 out of 5 average rating, 172 reviews
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds
9–14 Aug
4.98 out of 5 average rating, 159 reviews
Guest favourite
Cabin in Oakland
Cozy Cabin in the Woods
2 bedrooms, 5 beds
17–22 Jul
4.98 out of 5 average rating, 64 reviews
Top guest favourite
Yurt in Oakland
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
1 king bed
18–23 Aug
5.0 out of 5 average rating, 42 reviews
Top guest favourite
Home in Swanton
Bev's House at Sunny Meadows
3 bedrooms, 3 beds
20–25 Jul
4.97 out of 5 average rating, 303 reviews
Superhost
Cabin in Oakland
Incredible Cozy Cabin Immersed in Nature
3 bedrooms, 6 beds
1–6 Aug
4.85 out of 5 average rating, 447 reviews
Top guest favourite
Home in Oakland
Lake View Loft Lodge on Deep Creek Lake
2 bedrooms, 2 beds
21–26 Sept
4.94 out of 5 average rating, 170 reviews
Top guest favourite
Cabin in Oakland
Dog Friendly Cabin in the Woods, Hot Tub & Firepit
3 bedrooms, 4 beds
19–24 Jul
4.97 out of 5 average rating, 33 reviews