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Search results; Over 1,000 homes in Oakland

Guest favourite
Cabin in Oakland
Winter is Coming
3 bedrooms, 4 beds, 3 private bathrooms
22–27 Sept
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4.89 out of 5 average rating, 439 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
Guest favourite
Home in Oakland
Cottage on Jericho Road
3 bedrooms, 3 beds, 1 bathroom
23–28 Aug
4.84 out of 5 average rating, 25 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
Guest favourite
Home in Oakland
Victorian Farmhouse with view of pleasant valley
5 bedrooms, 6 beds, 2 bathrooms
20–25 Aug
4.89 out of 5 average rating, 110 reviews
Guest favourite
Cabin in Terra Alta
Unique Rustic Cabin w/ Lake Access & Kayak
1 bedroom, 1 king bed, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 14 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
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
Cottage in Oakland
Pet friendly-Cottage in the Woods
2 bedrooms, 3 beds, 1 bathroom
10–15 Oct
4.89 out of 5 average rating, 249 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, 21 reviews
Guest favourite
Camper van/Motorhome in Oakland
A quaint camper minutes from Deep Creek Lake
1 bedroom, 3 beds, 1 bathroom
19–24 Aug
4.88 out of 5 average rating, 17 reviews
Top guest favourite
Home in Oakland
Mountain Air Oasis with Hot Tub
3 bedrooms, 4 beds, 2.5 bathrooms
19–24 Aug
4.98 out of 5 average rating, 166 reviews
Top guest favourite
Yurt in Oakland
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
1 king bed, 1 bathroom
11–16 Sept
5.0 out of 5 average rating, 45 reviews
Top guest favourite
Tiny home in Oakland
The Original Hob
1 bedroom, 1 queen bed, 1 bathroom
20–25 Aug
4.98 out of 5 average rating, 204 reviews
Top guest favourite
Farm stay in Terra Alta
Pachamama’s Garden
1 bedroom, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 72 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
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
Guest favourite
Home in Oakland
LakeShore LoftHouse
2 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.93 out of 5 average rating, 40 reviews
Top guest favourite
Cabin in Oakland
Captain's Quarters Deep Creek Log Cabin Oasis
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 116 reviews