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Search results; Over 1,000 homes in Oakland

Guest favourite
Bungalow in Oakland
Secluded Private Lakefront Home -Pets Welcome
3 bedrooms, 6 beds, 2 bathrooms
13–18 Sept
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4.9 out of 5 average rating, 41 reviews
Top guest favourite
Tiny home in Oakland
The Grist Mill
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
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
Top guest favourite
Tiny home in Oakland
The Original Hob
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 204 reviews
Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds, 1 bathroom
27 Aug – 1 Sept
4.84 out of 5 average rating, 25 reviews
Guest favourite
Camper van/Motorhome in Oakland
A quaint camper minutes from Deep Creek Lake
1 bedroom, 3 beds, 1 bathroom
22–27 Aug
4.89 out of 5 average rating, 18 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds, 2 bathrooms
22–27 Aug
4.89 out of 5 average rating, 110 reviews
Guest favourite
Home in Oakland
The Other House
1 bedroom, 1 bed, 1 bathroom
24–29 Aug
4.95 out of 5 average rating, 22 reviews
Guest favourite
Home in Accident
Peaceful nature retreat nestled in a forested area
2 bedrooms, 2 queen beds, 1 bathroom
23–28 Aug
4.92 out of 5 average rating, 144 reviews
Top guest favourite
Cabin in Oakland
Romantic Cabin Walk to Lake & Dining/Hot tub/Dog
2 bedrooms, 2 beds, 1 bathroom
30 Oct – 4 Nov
5.0 out of 5 average rating, 113 reviews
Top guest favourite
Treehouse in McHenry
Bird's Eye View
1 bedroom, 3 beds, 1 bathroom
15–20 Nov
4.99 out of 5 average rating, 217 reviews
Guest favourite
Cabin in Oakland
Cozy Cabin in the Woods
2 bedrooms, 5 beds, 1.5 bathrooms
23–28 Aug
4.98 out of 5 average rating, 66 reviews
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds, 2.5 bathrooms
21–26 Aug
4.98 out of 5 average rating, 166 reviews
Top guest favourite
Tiny home in Swanton
Tiny House-Dream Catcher Cabin #2
1 bedroom, 1 king bed, 1.5 bathrooms
22–27 Aug
4.95 out of 5 average rating, 41 reviews
Top guest favourite
Cabin in Oakland
SUGARBUSH - Sweet Serenity Tiny House
1 bedroom, 1 queen bed, 1 bathroom
24–29 Aug
4.98 out of 5 average rating, 180 reviews
Top guest favourite
Home in Swanton
Bev's House at Sunny Meadows
3 bedrooms, 3 beds, 2 bathrooms
24–29 Aug
4.96 out of 5 average rating, 311 reviews
Guest favourite
Townhouse in Oakland
Lake View Condo with Grill and Wood Fireplace!
2 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
4.9 out of 5 average rating, 272 reviews
Superhost
Cabin in Mineral County
Glamping in a Creekside Aframe
1 bedroom, 1 queen bed, WC
27 Aug – 1 Sept
4.93 out of 5 average rating, 183 reviews
Guest favourite
Home in Oakland
Big Boulder Retreat! - at Deep Creek Lake
2 bedrooms, 3 beds, 1 bathroom
22–27 Aug
5.0 out of 5 average rating, 8 reviews