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Find Hotels with a Pool in Oakland, MD
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Check availability on Oakland Hotels with a Pool
Our top choices for Oakland hotels with a pool
New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!
New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!Oakland
10.0 out of 10, Exceptional, (13)
"The stay was great! Everyone loved the location and all the amenities provided! It was a great get away for all of our friends to get together and hangout! "
Becca V.
The price is ￥35,093
￥114,968 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Will O' The Wisp: 103A Efficiency/One Bath
Will O' The Wisp: 103A Efficiency/One BathOakland
9.6 out of 10, Exceptional, (8)
"This was my first time at Deep Creek, and I can’t wait to go back. The property was well maintained, and we loved the amenities available to us. We spent most of the weekend on the beach/docks directly out front, but also took advantage of the pool, spa, and sauna. Check in/out was easy, and all of the people we ran into were friendly. We will definitely be returning. "
Alice F.
The price is ￥38,289
￥49,293 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Will O' The Wisp: 107B One Bedroom/One Bath
Will O' The Wisp: 107B One Bedroom/One BathMountainside
10.0 out of 10, Exceptional, (2)
"Great place to visit. Hope to come back next year"
Stacy S.
The price is ￥41,363
￥50,474 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Suites at Silver Tree: A118 Studio Standard View
Suites at Silver Tree: A118 Studio Standard ViewOakland
10.0 out of 10, Exceptional, (2)
"Yes, we had a great time. Host was very accommodating."
Anonymous traveler
The price is ￥32,251
￥41,562 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Cove Creek Lodge: 210 Standard Double Queen Fireplace Room
Cove Creek Lodge: 210 Standard Double Queen Fireplace RoomOakland
10.0 out of 10, Exceptional, (9)
"Very nice room. Quiet and fantastic location!"
Julie S.
The price is ￥37,941
￥46,725 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Cove Creek Lodge: 215 Standard Double Queen Room
Cove Creek Lodge: 215 Standard Double Queen RoomOakland
10.0 out of 10, Exceptional, (2)
"It was very clean and the workers were so kind and was the perfect little get away for my family! "
Chris
The price is ￥37,337
￥45,884 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Cove Creek Lodge: 109 Lakeside Executive King Suite
Cove Creek Lodge: 109 Lakeside Executive King SuiteOakland
10.0 out of 10, Exceptional, (1)
"Staff was very helpful and cheerful. Room was very clean and a nice view. "
Jacqueline
The price is ￥42,061
￥54,090 total
includes taxes & fees
Dec 31 - Jan 1, 2026
10.0 out of 10, Exceptional, (4)
"I enjoyed the still of the area."
Shundrey
The price is ￥36,519
￥44,938 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.