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Search results; Over 1,000 homes in Oakland

Guest favourite
Cabin in Oakland
Lakehound Lodge - lake view, pet friendly
3 bedrooms, 3 beds, 3 private bathrooms
7–12 Sept
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4.92 out of 5 average rating, 268 reviews
Top guest favourite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed
1–6 Sept
5.0 out of 5 average rating, 181 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
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds
14–19 Sept
4.89 out of 5 average rating, 110 reviews
Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds
6–11 Sept
4.84 out of 5 average rating, 25 reviews
Top guest favourite
Treehouse in McHenry
Bird's Eye View
1 bedroom, 3 beds
20–25 Sept
4.99 out of 5 average rating, 217 reviews
Guest favourite
Cottage in Oakland
Pet friendly-Cottage in the Woods
2 bedrooms, 3 beds
10–15 Oct
4.89 out of 5 average rating, 249 reviews
Top guest favourite
Cabin in Aurora
Whispering Pines: Cabin in woods near Thomas/Davis
2 bedrooms, 3 beds
3–8 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Oakland
The Other House
1 bedroom, 1 bed
1–6 Sept
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Tiny home in Oakland
The Original Hob
1 bedroom, 1 queen bed
6–11 Sept
4.98 out of 5 average rating, 204 reviews
Top guest favourite
Farm stay in Terra Alta
Pachamama’s Garden
1 bedroom
7–12 Sept
5.0 out of 5 average rating, 74 reviews
Top guest favourite
Cabin in Oakland
SUGARBUSH - Sweet Serenity Tiny House
1 bedroom, 1 queen bed
7–12 Sept
4.98 out of 5 average rating, 180 reviews
Top guest favourite
Yurt in Oakland
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
1 king bed
4–9 Oct
5.0 out of 5 average rating, 45 reviews
Guest favourite
Camper van/Motorhome in Oakland
A quaint camper minutes from Deep Creek Lake
1 bedroom, 3 beds
7–12 Sept
4.89 out of 5 average rating, 18 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, 272 reviews
Guest favourite
Cottage in Oakland
Deep Creek Lake Cabin 3BR 1.5BA Honi, Wisp, & More
3 bedrooms, 6 beds
1–6 Sept
4.93 out of 5 average rating, 67 reviews
Guest favourite
Cabin in Oakland
C Box MountainTop
2 bedrooms, 3 beds
21–26 Sept
4.91 out of 5 average rating, 58 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, 113 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