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Search results; Over 1,000 homes in Oakland

Guest favourite
Chalet in Oakland
Lakefront A-Frame | Hot Tub, Private Dock, Views
5 bedrooms, 7 beds, 3 private bathrooms
1–6 Sept
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5.0 out of 5 average rating, 16 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds, 2 bathrooms
14–19 Sept
4.89 out of 5 average rating, 110 reviews
Guest favourite
Cabin in Oakland
Oakland Bear Lair|7BR Luxury Log|Pool, Hot tub
7 bedrooms, 12 beds, 4 bathrooms
20–25 Sept
4.91 out of 5 average rating, 22 reviews
Top guest favourite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed, 1 bathroom
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, 1 bathroom
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, 1 bathroom
6–11 Sept
4.84 out of 5 average rating, 25 reviews
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds, 2.5 bathrooms
13–18 Sept
4.98 out of 5 average rating, 166 reviews
Top guest favourite
Cabin in Oakland
Captain's Quarters Deep Creek Log Cabin Oasis
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 116 reviews
Guest favourite
Cabin in Oakland
Dar's Deep Creek Timber Hideaway
3 bedrooms, 6 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Oakland
Elegant Home Away: Hot Tub/Game Room/Kid-Friendly
4 bedrooms, 9 beds, 3.5 bathrooms
7–12 Sept
4.9 out of 5 average rating, 52 reviews
Superhost
Cabin in Oakland
2 great cabins - 1 special memory
5 bedrooms, 9 beds, 3 bathrooms
13–18 Sept
Guest favourite
Cabin in Oakland
Cozy Cabin in the Woods
2 bedrooms, 5 beds, 1.5 bathrooms
11–16 Sept
4.98 out of 5 average rating, 66 reviews
Top guest favourite
Home in Oakland
7-Bed Lake Retreat w/ Hot Tub & 5 mins to Wisp Ski
4 bedrooms, 7 beds, 4.5 bathrooms
8–13 Sept
4.98 out of 5 average rating, 57 reviews
Guest favourite
Home in Oakland
The Other House
1 bedroom, 1 bed, 1 bathroom
1–6 Sept
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Cabin in Oakland
Dog Friendly Cabin in the Woods, Hot Tub & Firepit
3 bedrooms, 4 beds, 1.5 bathrooms
19–24 Sept
4.97 out of 5 average rating, 34 reviews
Top guest favourite
Cabin in Oakland
CharmingHome7PersonHotTubFirePit2Arcades9MintoWisp
4 bedrooms, 10 beds, 3 bathrooms
7–12 Sept
5.0 out of 5 average rating, 113 reviews
Top guest favourite
Home in Oakland
The Barn @ Silo Farm | Deep Creek Lake, MD
2 bedrooms, 4 beds, 1.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 57 reviews
Home in Oakland
General Kelly Guesthouse
5 bedrooms, 6 beds, 2 bathrooms
1–6 Sept
4.83 out of 5 average rating, 166 reviews
Top guest favourite
Cabin in Swanton
Woodland Wish • Hot Tub•Sauna•Pickleball•Game Room
5 bedrooms, 8 beds, 4 bathrooms
25–30 Oct
4.96 out of 5 average rating, 81 reviews