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Search results; Over 1,000 homes in Oakland

Guest favourite
Chalet in Oakland
Spectacular Chalet, Timroc II, close to lake, Wisp
5 bedrooms, 9 beds, 3.5 private bathrooms
23–28 Aug
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4.92 out of 5 average rating, 140 reviews
Top guest favourite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed, 1 bathroom
15–20 Aug
5.0 out of 5 average rating, 177 reviews
Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds, 1 bathroom
23–28 Aug
4.82 out of 5 average rating, 22 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
Cottage in Oakland
Stone Haven
2 bedrooms, 4 beds, 1 bathroom
9–14 Aug
4.96 out of 5 average rating, 208 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds, 2 bathrooms
9–14 Aug
4.89 out of 5 average rating, 108 reviews
Top guest favourite
Treehouse in McHenry
Bird's Eye View
1 bedroom, 3 beds, 1 bathroom
15–20 Nov
4.99 out of 5 average rating, 214 reviews
Top guest favourite
Home in Swanton
Bev's House at Sunny Meadows
3 bedrooms, 3 beds, 2 bathrooms
19–24 Sept
4.96 out of 5 average rating, 307 reviews
Top guest favourite
Farm stay in Terra Alta
Pachamama’s Garden
1 bedroom, 1 bathroom
21–26 Aug
5.0 out of 5 average rating, 69 reviews
Guest favourite
Cottage in Oakland
Pet friendly-Cottage in the Woods
2 bedrooms, 3 beds, 1 bathroom
10–15 Oct
4.89 out of 5 average rating, 248 reviews
Guest favourite
Townhouse in Oakland
Lake View Condo with Grill and Wood Fireplace!
2 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
4.9 out of 5 average rating, 271 reviews
Guest favourite
Cabin in Oakland
Cozy Cabin in the Woods
2 bedrooms, 5 beds, 1.5 bathrooms
16–21 Aug
4.98 out of 5 average rating, 65 reviews
Top guest favourite
Cabin in Oakland
Captain's Quarters Deep Creek Log Cabin Oasis
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 115 reviews
Top guest favourite
Cabin in Terra Alta
Secluded Mountain Lake Escape w/ Dock & Kayaks
4 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.96 out of 5 average rating, 48 reviews
Top guest favourite
Cabin in Oakland
Romantic Cabin Walk to Lake & Dining/Hot tub/Dog
2 bedrooms, 2 beds, 1 bathroom
30 Oct – 4 Nov
5.0 out of 5 average rating, 111 reviews
Top guest favourite
Home in Oakland
Lake View Loft Lodge on Deep Creek Lake
2 bedrooms, 2 beds, 1 bathroom
21–26 Sept
4.94 out of 5 average rating, 174 reviews
Top guest favourite
Home in Oakland
Pet Friendly Cozy Home w/Hot Tub & Fire Pit at DCL
1 bedroom, 1 bed, 1 bathroom
9–14 Aug
4.95 out of 5 average rating, 38 reviews
Guest favourite
Holiday home in Oakland
1-Bedroom near Deep Creek Lake with Mountain View
1 bedroom, 1 bed, 1 bathroom
18–23 Aug
4.91 out of 5 average rating, 58 reviews
Top guest favourite
Yurt in Oakland
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
1 king bed, 1 bathroom
11–16 Sept
5.0 out of 5 average rating, 44 reviews