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Search results; Over 1,000 homes in Oakland

Top guest favourite
Cabin in Oakland
SUGARBUSH - Sweet Serenity Tiny House
1 bedroom, 1 bed, 1 private bathroom
6–11 Aug
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4.98 out of 5 average rating, 179 reviews
Top guest favourite
Cabin in Oakland
Oakland Bear Lair | 7BR Luxury Log | Pool, Hot tub
7 bedrooms, 10 beds, 4 bathrooms
20–25 Sept
5.0 out of 5 average rating, 18 reviews
Superhost
Cabin in Oakland
2 great cabins - 1 special memory
5 bedrooms, 9 beds, 3 bathrooms
30 Aug – 4 Sept
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds, 2 bathrooms
10–15 Aug
4.89 out of 5 average rating, 104 reviews
Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds, 1 bathroom
10–15 Aug
4.78 out of 5 average rating, 18 reviews
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds, 2.5 bathrooms
9–14 Aug
4.98 out of 5 average rating, 161 reviews
Superhost
Cabin in Oakland
Dar's Deep Creek Timber Hideaway
3 bedrooms, 6 beds, 2 bathrooms
2–7 Aug
Top guest favourite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed, 1 bathroom
26–31 Jul
5.0 out of 5 average rating, 175 reviews
Top guest favourite
Cabin in Oakland
Dancing Bears
3 bedrooms, 4 beds, 1 bathroom
29 Jul – 3 Aug
4.96 out of 5 average rating, 228 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, 111 reviews
Guest favourite
Cottage in Oakland
Deep Creek Lake Cabin 3BR 1.5BA Honi, Wisp, & More
3 bedrooms, 6 beds, 1.5 bathrooms
26–31 Jul
4.93 out of 5 average rating, 67 reviews
Flat in Oakland
Charming 1-bdrm with balcony, Close to Everything.
1 bedroom, 1 single bed, 1 bathroom
27 Jul – 1 Aug
4.72 out of 5 average rating, 25 reviews
Guest favourite
Home in Oakland
The Other House
1 bedroom, 1 bed, 1 bathroom
26–31 Jul
4.95 out of 5 average rating, 19 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
Superhost
Home in Swanton
Lakefront w Private Dock, Hot Tub, Large Yard
5 bedrooms, 7 beds, 3.5 bathrooms
8–13 Aug
New place to stay
Top guest favourite
Home in Oakland
Deep Creek Dome Cabin | Fire Pit & EV Near Wisp
4 bedrooms, 6 beds, 3 bathrooms
23–28 Aug
4.96 out of 5 average rating, 45 reviews
Guest favourite
Home in Oakland
7-Bed Lake Retreat w/ Hot Tub & 5 mins to Wisp Ski
4 bedrooms, 7 beds, 4.5 bathrooms
22–27 Aug
4.98 out of 5 average rating, 51 reviews
Guest favourite
Cabin in Oakland
Quiet 2 bdrm cottage w/firepit & trees
2 bedrooms, 4 beds, 1 bathroom
16–21 Aug
4.9 out of 5 average rating, 84 reviews
Top guest favourite
Cabin in Oakland
CharmingHome7PersonHotTubFirePit2Arcades9MintoWisp
4 bedrooms, 10 beds, 3 bathrooms
9–14 Aug
5.0 out of 5 average rating, 105 reviews