filters

Search results; Over 1,000 homes in Oakland

Photo 1 of 22
Top guest favourite
Tiny home in Oakland
Lil' Sumpin
1 bedroom, 1 bed, 1 private bathroom
21–26 Sept
,
5.0 out of 5 average rating, 86 reviews
Photo 1 of 29
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds
12–17 Oct
4.88 out of 5 average rating, 112 reviews
Photo 1 of 10
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
Photo 1 of 21
Top guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds
4–9 Oct
4.88 out of 5 average rating, 32 reviews
Photo 1 of 29
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds
20–25 Sept
4.98 out of 5 average rating, 170 reviews
Photo 1 of 19
Top guest favourite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed
27 Sept – 2 Oct
5.0 out of 5 average rating, 192 reviews
Photo 1 of 29
Top guest favourite
Cabin in Oakland
Captain's Quarters Deep Creek Log Cabin Oasis
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 122 reviews
Photo 1 of 23
Guest favourite
Home in Oakland
The Other House
1 bedroom, 1 bed
20–25 Sept
4.92 out of 5 average rating, 26 reviews
Photo 1 of 29
Superhost
Cabin in Oakland
Incredible Cozy Cabin Immersed in Nature
3 bedrooms, 6 beds
28 Sept – 3 Oct
4.84 out of 5 average rating, 459 reviews
Photo 1 of 29
Top guest favourite
Home in Oakland
Historic 6BR Family Getaway
6 bedrooms, 7 beds
18–23 Oct
5.0 out of 5 average rating, 8 reviews
Photo 1 of 29
Guest favourite
Home in Oakland
"Das Haus Am See" (the house at the lake)
3 bedrooms, 3 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 17 reviews
Photo 1 of 29
Guest favourite
Home in McHenry
Cozy Lake House with Dock
3 bedrooms, 6 beds
11–16 Oct
4.93 out of 5 average rating, 121 reviews
Photo 1 of 20
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
Photo 1 of 29
Top guest favourite
Cabin in Oakland
Dog Friendly Cabin in the Woods, Hot Tub & Firepit
3 bedrooms, 4 beds
20–25 Sept
4.97 out of 5 average rating, 34 reviews
Photo 1 of 29
Top guest favourite
Home in Oakland
Deep Creek Dome Cabin | Fire Pit & EV Near Wisp
4 bedrooms, 6 beds
18–23 Oct
4.95 out of 5 average rating, 58 reviews
Photo 1 of 29
Guest favourite
Cabin in Oakland
Cabin near lake, family & pet friendly, hot tub!
3 bedrooms, 5 beds
11–16 Oct
4.92 out of 5 average rating, 97 reviews
Photo 1 of 29
Guest favourite
Home in Oakland
Private Lodge sleeps 31 guests Spectacular Views
8 bedrooms, 16 beds
12–17 Oct
4.91 out of 5 average rating, 57 reviews
Photo 1 of 29
Guest favourite
Home in Oakland
Pet Friendly Cozy Home w/Hot Tub & Fire Pit at DCL
1 bedroom, 1 bed
20–25 Sept
4.95 out of 5 average rating, 41 reviews
Photo 1 of 29
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