filters

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
26–31 Aug
,
4.96 out of 5 average rating, 172 reviews
Top guest favourite
Yurt in Oakland
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
5.0 out of 5 average rating, 41 reviews, 1 bed, 1 bathroom
6–11 Jul
Top guest favourite
Home in Oakland
The Other House
5.0 out of 5 average rating, 16 reviews, 1 bedroom, 1 bed, 1 bathroom
5–10 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
13–18 Sept
Top guest favourite
Tiny home in Oakland
The Grist Mill
5.0 out of 5 average rating, 169 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
Top guest favourite
Barn in Oakland
Couples Retreat: The HayLoft- Rustic Escape For 2
5.0 out of 5 average rating, 17 reviews, 1 bedroom, 1 bed, 1 bathroom
5–10 Jul
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
Superhost
Loft in Oakland
One bedroom Loft-15 from WISP & close to Walmart
4.73 out of 5 average rating, 86 reviews, 1 bedroom, 1 bed, 1 bathroom
5–10 Jul
Top guest favourite
Home in McHenry
Newly Renovated 2 Bed/2 Bath in Deep Creek
4.95 out of 5 average rating, 385 reviews, 2 bedrooms, 2 beds, 2 bathrooms
12–17 Jul
Top guest favourite
Cabin in Oakland
Luxury 7BR Cabin|HotTub|HeatedPool
5.0 out of 5 average rating, 17 reviews, 7 bedrooms, 10 beds, 4 bathrooms
7–12 Oct
Top guest favourite
Cabin in Oakland
Speakeasy | Bunk Room | Hot Tub | Private 2 acres
4.98 out of 5 average rating, 41 reviews, 3 bedrooms, 7 beds, 3.5 bathrooms
27 Jul – 1 Aug
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
Treehouse in McHenry
Bird's Eye View
4.99 out of 5 average rating, 204 reviews, 1 bedroom, 3 beds, 1 bathroom
15–20 Nov
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
6–11 Jul
Top guest favourite
Cabin in Accident
Rustic Luxe Cabin (4x4 Required)
4.98 out of 5 average rating, 92 reviews, 2 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
Guest favourite
Cottage in Oakland
Pet friendly-Cottage in the Woods
4.9 out of 5 average rating, 242 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Guest favourite
Cabin in Oakland
Cozy Cabin in the Woods
4.98 out of 5 average rating, 63 reviews, 2 bedrooms, 5 beds, 1.5 bathrooms
12–17 Jul
Cabin in Oakland
Incredible Cozy Cabin Immersed in Nature
4.85 out of 5 average rating, 447 reviews, 3 bedrooms, 6 beds, 1 bathroom
12–17 Jul
Top guest favourite
Home in Oakland
DCL Cottage with MD State Park Pass
4.98 out of 5 average rating, 81 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
6–11 Jul