Find Hotels with a Pool in Oakland, MD

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Check availability on Oakland Hotels with a Pool

Tonight
Mar 29 - Mar 30
Tomorrow
Mar 30 - Mar 31
Next weekend
Apr 3 - Apr 5
In two weeks
Apr 10 - Apr 12

Our top choices for Oakland hotels with a pool

Exterior

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 reviews)
"Great spot for a team retreat!"
United States
Garrett H.
The price is ￥36,070
￥117,658 total
includes taxes & fees
Mar 31 - Apr 1
New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!
Indoor pool, a heated pool

Will O' The Wisp: 107B One Bedroom/One Bath

Will O' The Wisp: 107B One Bedroom/One Bath
Mountainside
10.0 out of 10, Exceptional, (2 reviews)
"Great place to visit. Hope to come back next year"
United States
Stacy S.
The price is ￥39,951
￥49,791 total
includes taxes & fees
Apr 12 - Apr 13
Will O' The Wisp: 107B One Bedroom/One Bath
Exterior

Cove Creek Lodge: 210 Standard Double Queen Fireplace Room

Cove Creek Lodge: 210 Standard Double Queen Fireplace Room
Oakland
10.0 out of 10, Exceptional, (11 reviews)
"We had a wonderful stay. The room was exactly as advertised online, clean, comfortable, and welcoming. I would absolutely recommend this place and would stay here again."
United States
Farlon
The price is ￥37,578
￥48,107 total
includes taxes & fees
Apr 2 - Apr 3
Cove Creek Lodge: 210 Standard Double Queen Fireplace Room
Exterior

Cove Creek Lodge: 208 King Room ADA Accessible

Cove Creek Lodge: 208 King Room ADA Accessible
Oakland
10.0 out of 10, Exceptional, (4 reviews)
"I enjoyed the still of the area."
United States
Shundrey
The price is ￥36,095
￥45,056 total
includes taxes & fees
Apr 12 - Apr 13
Cove Creek Lodge: 208 King Room ADA Accessible
Exterior

Cove Creek Lodge: 209 Standard Double Queen Room

Cove Creek Lodge: 209 Standard Double Queen Room
Oakland
The price is ￥36,886
￥45,960 total
includes taxes & fees
Apr 12 - Apr 13
Cove Creek Lodge: 209 Standard Double Queen Room
Exterior

Cove Creek Lodge: 220 Lakeside Double Queen Fireplace Room

Cove Creek Lodge: 220 Lakeside Double Queen Fireplace Room
Oakland
9.0 out of 10, Wonderful, (2 reviews)
"Spontaneous trip and we lucked out finding this room on Expedia. Property is newly renovated and our room had beautiful a frame ceiling and a fireplace. Sat outside on the deck and enjoy the lake view. Would definitely go back!"
United States
Samantha
The price is ￥42,238
￥52,740 total
includes taxes & fees
Apr 12 - Apr 13
Cove Creek Lodge: 220 Lakeside Double Queen Fireplace Room
Exterior

Cove Creek Lodge: 202 Poolside Double Queen Room

Cove Creek Lodge: 202 Poolside Double Queen Room
Oakland
10.0 out of 10, Exceptional, (1 review)
"Very close to everything, nice lodge!"
United States
Celerina
The price is ￥38,438
￥47,896 total
includes taxes & fees
Apr 12 - Apr 13
Cove Creek Lodge: 202 Poolside Double Queen Room
Exterior

Cove Creek Lodge: 205 Poolside Double Queen Room

Cove Creek Lodge: 205 Poolside Double Queen Room
Oakland
The price is ￥38,438
￥47,896 total
includes taxes & fees
Apr 12 - Apr 13
Cove Creek Lodge: 205 Poolside Double Queen Room
Exterior

Cove Creek Lodge: 207 Standard Double Queen Fireplace Room

Cove Creek Lodge: 207 Standard Double Queen Fireplace Room
Oakland
9.0 out of 10, Wonderful, (2 reviews)
"Smooth commutation, beautiful accomodations"
United States
Tiffany M.
The price is ￥37,578
￥46,918 total
includes taxes & fees
Apr 12 - Apr 13
Cove Creek Lodge: 207 Standard Double Queen Fireplace Room
Exterior

Cove Creek Lodge: 214 Standard Double Queen Fireplace Room

Cove Creek Lodge: 214 Standard Double Queen Fireplace Room
Oakland
9.0 out of 10, Wonderful, (2 reviews)
"Well located for our trip. We wanted to explore the area and things to do in anticipation of our whole family meeting in the Deep Creek area. Near excellent coffee (Trader), modest bakery and dining options."
United States
Eric
The price is ￥37,578
￥46,918 total
includes taxes & fees
Apr 12 - Apr 13
Cove Creek Lodge: 214 Standard Double Queen Fireplace 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.
View all properties

Choose what matters most at hotels with a pool in Oakland

Breakfast included
Hot tub

Hotels with pools and hot tubs in Oakland

Exterior
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!

New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!
Oakland
10.0 out of 10, Exceptional, (13)
The price is ￥36,070
￥117,658 total
includes taxes & fees
Mar 31 - Apr 1
New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!
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.
View all properties

Top Oakland Hotel Reviews

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 29 places to stay with pools. During your trip, you can explore sights such as Herrington Manor State Park and Swallow Falls State Park, and then relax and unwind poolside at one of the accommodations in Oakland that guests like for their pools.
What are some accommodations with pools in Oakland?
The Garrett Inn: Cottage, 15-minute walk from Deep Creek Lake. Features complimentary wireless internet access, a communal pool, and kitchens.
How many pool hotels will I be able to find in Oakland?
Expedia's 29 hotels in Oakland give you a great choice for your poolside getaway.
What is there to see and do in Oakland?
The picturesque setting of Deep Creek Lake and Youghiogheny River showcase the area's natural beauty. During your stay, check out sights such as Herrington Manor State Park, Swallow Falls State Park, and Lower Deep Creek Heritage Conservation Fund Site. 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.