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Search results; Over 1,000 homes in Oakland

Top guest favourite
Chalet in Oakland
Happy Our Retreat. Amazing Lake/Mtn Views!
3 bedrooms, 4 beds, 2 private bathrooms
31 Aug – 5 Sept
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4.96 out of 5 average rating, 172 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
4.89 out of 5 average rating, 104 reviews, 5 bedrooms, 6 beds, 2 bathrooms
10–15 Aug
Home in Oakland
Cottage on Jericho Road
4.75 out of 5 average rating, 16 reviews, 3 bedrooms, 3 beds, 1 bathroom
18–23 Jul
Guest favourite
Home in McHenry
Deep Creek Gem: Hot Tub, Spa Bath & Game Room
4.97 out of 5 average rating, 101 reviews, 4 bedrooms, 6 beds, 2 bathrooms
19–24 Jul
Guest favourite
Home in Oakland
Historic 6BR Family Getaway
5.0 out of 5 average rating, 6 reviews, 6 bedrooms, 7 beds, 2.5 bathrooms
21–26 Jul
Top guest favourite
Home in Oakland
The Other House
4.94 out of 5 average rating, 17 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Guest favourite
Home in Oakland
"Das Haus Am See" (the house at the lake)
5.0 out of 5 average rating, 14 reviews, 3 bedrooms, 3 beds, 3 bathrooms
14–19 Jul
Home in Oakland
Secluded Oakland Gem w/ Hot Tub: Dogs Welcome!
4.88 out of 5 average rating, 52 reviews, 3 bedrooms, 4 beds, 2 bathrooms
7–12 Jul
Top guest favourite
Cabin in Terra Alta
Peaceful Cabin w/ Private Dock & Kayaks
4.95 out of 5 average rating, 40 reviews, 4 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Home in Oakland
Spring is in the air at our Lake View Condo!
4.97 out of 5 average rating, 122 reviews, 3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
Guest favourite
Camper van/Motorhome in Oakland
A quaint camper minutes from Deep Creek Lake
4.93 out of 5 average rating, 14 reviews, 1 bedroom, 3 beds, 1 bathroom
12–17 Jul
Top guest favourite
Tiny home in Oakland
Lil' Sumpin
5.0 out of 5 average rating, 81 reviews, 1 bedroom, 1 bed, 1 bathroom
11–16 Jul
Top guest favourite
Cabin in Oakland
Romantic Cabin Walk to Lake & Dining/Hot tub/Dogs
5.0 out of 5 average rating, 102 reviews, 2 bedrooms, 2 beds, 1 bathroom
25–30 Oct
Top guest favourite
Home in Oakland
DCL Cottage with MD State Park Pass
4.98 out of 5 average rating, 82 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Jul
Top guest favourite
Cabin in Oakland
C Box MountainTop
4.94 out of 5 average rating, 51 reviews, 2 bedrooms, 3 beds, 2 bathrooms
7–12 Jul
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
4.98 out of 5 average rating, 158 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
12–17 Jul
Home in Oakland
Lucy’s Lookout
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 4 beds, 2 bathrooms
22–27 Jul
Guest favourite
Cabin in Oakland
Cabin near lake, family & pet friendly, hot tub!
4.92 out of 5 average rating, 85 reviews, 3 bedrooms, 5 beds, 3 bathrooms
19–24 Jul
Top guest favourite
Home in Oakland
7-Bed Lake Retreat w/ Hot Tub & 5 mins to Wisp Ski
5.0 out of 5 average rating, 48 reviews, 4 bedrooms, 7 beds, 4.5 bathrooms
22–27 Aug