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Find Hotels with a Pool in Oakland, MD

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Check availability on Oakland Hotels with a Pool

Top Oakland Hotels with a Pool

Property grounds
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!

2.0 star property
Oakland
10.0 out of 10, Exceptional, (10)
"This is an incredible house in a beautiful location. Shawn was more than helpful and an incredible host. We will definitely be returning renters. "
United States
chris s.
The price is ￥34,619
￥111,943 total
includes taxes & fees
Dec 3 - Dec 4
New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!
Interior
Suites at Silver Tree: A310 Studio & Loft Standard View

Suites at Silver Tree: A310 Studio & Loft Standard View

Oakland
10.0 out of 10, Exceptional, (4)
"First time at Deep Lake and the condo. Loved our time there. Highly recommended. We will be back!!"
United States
Phuong M.
The price is ￥48,402
￥62,222 total
includes taxes & fees
Dec 7 - Dec 8
Suites at Silver Tree: A310 Studio & Loft Standard View
Smart TV, video games
In the heart of Deep Creek Lake! - "Shamrock Inn"

In the heart of Deep Creek Lake! - "Shamrock Inn"

Mountainside
9.6 out of 10, Exceptional, (5)
"Awesome "
United States
Mariam H.
The price is ￥29,071
￥71,772 total
includes taxes & fees
Nov 16 - Nov 17
In the heart of Deep Creek Lake! - "Shamrock Inn"
A heated pool
Cove Creek Lodge: 208 King Room ADA Accessible

Cove Creek Lodge: 208 King Room ADA Accessible

2.0 star property
Oakland
10.0 out of 10, Exceptional, (4)
"Clean, comfortable, newly renovated room, nicely furnished with modern design. Location is perfect to all areas around Deep Creek Lake."
United States
Gregory K.
The price is ￥45,619
￥58,886 total
includes taxes & fees
Nov 18 - Nov 19
Cove Creek Lodge: 208 King Room ADA Accessible
A heated pool
Cove Creek Lodge: 210 Standard Double Queen Fireplace Room

Cove Creek Lodge: 210 Standard Double Queen Fireplace Room

2.0 star property
Oakland
10.0 out of 10, Exceptional, (9)
"What a wonderful place"
United States
Edna S.
The price is ￥46,101
￥59,436 total
includes taxes & fees
Nov 18 - Nov 19
Cove Creek Lodge: 210 Standard Double Queen Fireplace Room
Indoor pool, a heated pool
Will O' The Wisp: 103A Efficiency/One Bath

Will O' The Wisp: 103A Efficiency/One Bath

Oakland
9.6 out of 10, Exceptional, (8)
"Rekaxing, restful, beautiful views"
United States
Donald D.
The price is ￥43,898
￥56,597 total
includes taxes & fees
Nov 25 - Nov 26
Will O' The Wisp: 103A Efficiency/One Bath
A heated pool
Cove Creek Lodge: 109 Lakeside Executive King Suite

Cove Creek Lodge: 109 Lakeside Executive King Suite

2.0 star property
Oakland
10.0 out of 10, Exceptional, (1)
"Staff was very helpful and cheerful. Room was very clean and a nice view. "
United States
Jacqueline
The price is ￥49,284
￥63,391 total
includes taxes & fees
Nov 29 - Nov 30
Cove Creek Lodge: 109 Lakeside Executive King Suite
A heated pool
Cove Creek Lodge: 201 Poolside Double Queen Fireplace Room

Cove Creek Lodge: 201 Poolside Double Queen Fireplace Room

2.0 star property
Oakland
10.0 out of 10, Exceptional, (5)
"We had a wonderful time, very clean, staff was super helpful"
United States
Bruce D.
The price is ￥47,210
￥60,863 total
includes taxes & fees
Nov 25 - Nov 26
Cove Creek Lodge: 201 Poolside Double Queen Fireplace Room
A heated pool
Cove Creek Lodge: 216 Lakeside Double Queen Room

Cove Creek Lodge: 216 Lakeside Double Queen Room

2.0 star property
Oakland
10.0 out of 10, Exceptional, (1)
"Such a cute place on the lake! The common areas were great and the bar looked cool! The room was so cozy and comfortable - loved all the branded mugs and wine glasses! Property was perfect and had so many cute places to relax"
United States
Gillian W.
The price is ￥47,581
￥61,450 total
includes taxes & fees
Nov 16 - Nov 17
Cove Creek Lodge: 216 Lakeside Double Queen Room
A heated pool
Cove Creek Lodge: 203 Poolside Double Queen Room

Cove Creek Lodge: 203 Poolside Double Queen Room

2.0 star property
Oakland
10.0 out of 10, Exceptional, (4)
"Check in a breeze fun trip thanks"
United States
Mike O.
The price is ￥47,210
￥60,863 total
includes taxes & fees
Nov 29 - Nov 30
Cove Creek Lodge: 203 Poolside Double Queen Room
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.
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Top Oakland Hotel Reviews

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Frequently asked questions

What's it like visiting Oakland?
If taking it easy by the pool is your idea of the perfect getaway, you may want to consider luxurious Oakland, which has 19 places to stay with pools. During your trip, you can explore sights such as Deep Creek Lake, and then relax and unwind poolside at one of the accommodations in Oakland that travelers like for their pools.
What are some accommodations with pools in Oakland?
Baja Motel: Vacation home, 5-minute walk from Deep Creek Lake. Features kitchens, a communal pool, and televisions. The Garrett Inn: Cabin, 11-minute walk from Deep Creek Lake. Features kitchens, a communal pool, and Smart TVs.
How many pool hotels will I be able to find in Oakland?
Expedia's 19 hotels in Oakland give you a great choice for your poolside getaway.
What is there to see and do in Oakland?
Explore places like Deep Creek Lake while you're in Oakland. Spend some time experiencing the great outdoors at Youghiogheny River and Oakland Dog Park. Take in the natural beauty of Oakland with the lakeside setting and riverfront.
When is the best time to book a hotel with a pool in Oakland?
Taking into account the local weather in Oakland can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 32°F. The snowiest months in Oakland are January, December, February, and May, with each month seeing an average of 31 inches of snowfall.