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Search results; Over 1,000 homes in Oakland

Top guest favourite
Cottage in Oakland
Stone Haven
2 bedrooms, 3 beds, 1 private bathroom
11–16 Sept
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4.96 out of 5 average rating, 214 reviews
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds, 2 bathrooms
28 Sept – 3 Oct
4.88 out of 5 average rating, 111 reviews
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds, 2.5 bathrooms
13–18 Sept
4.98 out of 5 average rating, 168 reviews
Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.85 out of 5 average rating, 27 reviews
Top guest favourite
Cabin in Oakland
Dar's Deep Creek Timber Hideaway
3 bedrooms, 6 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Oakland
Deep Creek Dome Cabin | Fire Pit & EV Near Wisp
4 bedrooms, 6 beds, 3 bathrooms
4–9 Oct
4.94 out of 5 average rating, 54 reviews
Top guest favourite
Home in Oakland
Elegant Home Away: Hot Tub/Game Room/Kid-Friendly
4 bedrooms, 9 beds, 3.5 bathrooms
7–12 Sept
4.91 out of 5 average rating, 54 reviews
Guest favourite
Cabin in Oakland
Cabin near lake, family & pet friendly, hot tub!
3 bedrooms, 5 beds, 3 bathrooms
21–26 Sept
4.92 out of 5 average rating, 95 reviews
Top guest favourite
Cabin in Oakland
Speakeasy | Bunk Room | Hot Tub | Private 2 acres
3 bedrooms, 7 beds, 3.5 bathrooms
7–12 Sept
4.98 out of 5 average rating, 50 reviews
Top guest favourite
Home in Oakland
Lucy’s Lookout
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.93 out of 5 average rating, 15 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
Home in Oakland
Broadford Park View
5 bedrooms, 8 beds, 3.5 bathrooms
20–25 Sept
4.95 out of 5 average rating, 41 reviews
Top guest favourite
Home in Oakland
DCL Cottage with MD State Park Pass
3 bedrooms, 4 beds, 2.5 bathrooms
13–18 Sept
4.98 out of 5 average rating, 86 reviews
Guest favourite
Home in Oakland
Private Lodge sleeps 31 guests Spectacular Views
8 bedrooms, 16 beds, 5 bathrooms
13–18 Sept
4.91 out of 5 average rating, 55 reviews
Top guest favourite
Townhouse in McHenry
Our Lovely Lake Retreat
3 bedrooms, 4 beds, 2.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 109 reviews
Top guest favourite
Home in Swanton
Almost Heaven
4 bedrooms, 7 beds, 3 bathrooms
12–17 Oct
5.0 out of 5 average rating, 34 reviews
Top guest favourite
Cabin in Oakland
Captain's Quarters Deep Creek Log Cabin Oasis
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 121 reviews
Top guest favourite
Home in Oakland
Historic 6BR Family Getaway
6 bedrooms, 7 beds, 2.5 bathrooms
18–23 Oct
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Oakland
Shamrock Inn | Hot Tub + Lakefront Clubhouse
3 bedrooms, 6 beds, 2.5 bathrooms
7–12 Sept
4.96 out of 5 average rating, 97 reviews