filters

Search results; Over 1,000 homes in Oakland

Guest favourite
Hut in Oakland
Large estate, miles of trails, cozy hut Cortina
1 bedroom, 2 beds, 6 shared bathrooms
5–10 Jul
,
4.91 out of 5 average rating, 102 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds
10–15 Aug
4.89 out of 5 average rating, 104 reviews
Guest favourite
Home in Oakland
Historic 6BR Family Getaway
6 bedrooms, 7 beds
21–26 Jul
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Cabin in Oakland
Romantic Cabin Walk to Lake & Dining/Hot tub/Dogs
2 bedrooms, 2 beds
13–18 Sept
5.0 out of 5 average rating, 101 reviews
Superhost
Home in Swanton
Deep Creek Lake, Wisp, Dog Friendly
3 bedrooms, 4 beds
5–10 Jul
4.85 out of 5 average rating, 80 reviews
Top guest favourite
Home in Oakland
Elegant Home Away: Hot Tub/Game Room/Kid-Friendly
4 bedrooms, 9 beds
19–24 Jul
4.9 out of 5 average rating, 49 reviews
Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds
18–23 Jul
4.77 out of 5 average rating, 13 reviews
Top guest favourite
Home in Oakland
The Other House
1 bedroom, 1 bed
5–10 Jul
5.0 out of 5 average rating, 15 reviews
Guest favourite
Cabin in Oakland
Cabin near lake, family & pet friendly, hot tub!
3 bedrooms, 5 beds
6–11 Jul
4.92 out of 5 average rating, 85 reviews
Guest favourite
Cabin in Terra Alta
Hike, Ski & Raft: Terra Alta Cabin w/ Large Deck
3 bedrooms, 7 beds
12–17 Jul
4.85 out of 5 average rating, 41 reviews
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds
12–17 Jul
4.98 out of 5 average rating, 157 reviews
Superhost
Loft in Oakland
One bedroom Loft-15 from WISP & close to Walmart
1 bedroom, 1 queen bed
4–9 Jul
4.73 out of 5 average rating, 86 reviews
Top guest favourite
Home in Oakland
DCL Cottage with MD State Park Pass
3 bedrooms, 4 beds
6–11 Jul
4.98 out of 5 average rating, 81 reviews
Home in Oakland
Secluded Oakland Gem w/ Hot Tub: Dogs Welcome!
3 bedrooms, 4 beds
7–12 Jul
4.88 out of 5 average rating, 51 reviews
Top guest favourite
Cabin in Oakland
Pool, HotTub, FirePit, EVCharger, & Great Location
6 bedrooms, 10 beds
5–10 Jul
4.98 out of 5 average rating, 122 reviews
Home in Oakland
Lucy’s Lookout
3 bedrooms, 4 beds
22–27 Jul
New place to stay
Top guest favourite
Cabin in McHenry
Skyeia Cabin on Deep Creek Lake
2 bedrooms, 3 beds
18–23 Aug
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Cabin in Oakland
Speakeasy | Bunk Room | Hot Tub | Private 2 acres
3 bedrooms, 7 beds
27 Jul – 1 Aug
4.98 out of 5 average rating, 41 reviews
Top guest favourite
Home in McHenry
Newly Renovated 2 Bed/2 Bath in Deep Creek
2 bedrooms, 2 queen beds
12–17 Jul
4.95 out of 5 average rating, 384 reviews