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Search results; Over 1,000 homes in Oakland

Top guest favorite
Cabin in Oakland
Dancing Bears
3 bedrooms, 4 beds, 1 private bath
Aug 16 – 21
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4.97 out of 5 average rating, 230 reviews
Top guest favorite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed, 1 bath
Aug 15 – 20
5.0 out of 5 average rating, 181 reviews
Guest favorite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds, 2 baths
Aug 17 – 22
4.89 out of 5 average rating, 108 reviews
Guest favorite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds, 1 bath
Aug 23 – 28
4.83 out of 5 average rating, 23 reviews
Top guest favorite
Cottage in Oakland
Stone Haven
2 bedrooms, 4 beds, 1 bath
Aug 25 – 30
4.96 out of 5 average rating, 208 reviews
Top guest favorite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds, 2.5 baths
Aug 23 – 28
4.98 out of 5 average rating, 164 reviews
Guest favorite
Cabin in Oakland
Oakland Bear Lair|7BR Luxury Log|Pool, Hot tub
7 bedrooms, 12 beds, 4 baths
Sep 20 – 25
4.95 out of 5 average rating, 20 reviews
Apartment in Oakland
Large 2-bdrm apt. Walking distance to everything
2 bedrooms, 2 beds, 1 bath
Dec 28 – Jan 2
4.82 out of 5 average rating, 84 reviews
Top guest favorite
Cabin in Oakland
Captain's Quarters Deep Creek Log Cabin Oasis
2 bedrooms, 3 beds, 1 bath
Aug 17 – 22
4.97 out of 5 average rating, 116 reviews
Top guest favorite
Cabin in Oakland
Speakeasy | Bunk Room | Hot Tub | Private 2 acres
3 bedrooms, 7 beds, 3.5 baths
Sep 7 – 12
4.98 out of 5 average rating, 46 reviews
Top guest favorite
Cabin in Oakland
Romantic Cabin Walk to Lake & Dining/Hot tub/Dog
2 bedrooms, 2 beds, 1 bath
Oct 30 – Nov 4
5.0 out of 5 average rating, 111 reviews
Guest favorite
Home in Oakland
The Other House
1 bedroom, 1 bed, 1 bath
Aug 15 – 20
4.95 out of 5 average rating, 21 reviews
Guest favorite
Cottage in Oakland
Deep Creek Lake Cabin 3BR 1.5BA Honi, Wisp, & More
3 bedrooms, 6 beds, 1.5 baths
Aug 18 – 23
4.93 out of 5 average rating, 67 reviews
Top guest favorite
Cabin in Oakland
CharmingHome7PersonHotTubFirePit2Arcades9MintoWisp
4 bedrooms, 10 beds, 3 baths
Aug 16 – 21
5.0 out of 5 average rating, 111 reviews
Top guest favorite
Cabin in Oakland
SUGARBUSH - Sweet Serenity Tiny House
1 bedroom, 1 queen bed, 1 bath
Aug 16 – 21
4.98 out of 5 average rating, 180 reviews
Guest favorite
Cabin in Oakland
Cozy Cabin in the Woods
2 bedrooms, 5 beds, 1.5 baths
Aug 23 – 28
4.98 out of 5 average rating, 65 reviews
Top guest favorite
Tiny home in Oakland
The Original Hob
1 bedroom, 1 queen bed, 1 bath
Aug 16 – 21
4.98 out of 5 average rating, 203 reviews
Top guest favorite
Cabin in Oakland
Dar's Deep Creek Timber Hideaway
3 bedrooms, 6 beds, 2 baths
Aug 24 – 29
5.0 out of 5 average rating, 5 reviews
Top guest favorite
Home in Oakland
Deep Creek Dome Cabin | Fire Pit & EV Near Wisp
4 bedrooms, 6 beds, 3 baths
Sep 28 – Oct 3
4.96 out of 5 average rating, 51 reviews