Photo by Jenn Charbonneau

Oakland Hotel Guide - Hotels with Pool in Oakland, Maryland

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Check availability on Oakland Hotels with Pool

Tonight
22 Nov - 23 Nov
Tomorrow
23 Nov - 24 Nov
Next weekend
28 Nov - 30 Nov
In two weeks
5 Dec - 7 Dec

Top Oakland Hotels with 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
  • Hot tub
10.0 out of 10, Exceptional, (11)
Sparkling waters beckon from the hot tub where mountain adventures conclude in pure relaxation. This cabin blends outdoor enjoyment with indoor entertainment through arcade games, barbecue areas, and a cosy fireplace for perfect lakeside memories.
The price is €646
includes taxes & fees
3 Dec - 4 Dec
New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!
Interior
Suites at Silver Tree: A118 Studio Standard View

Suites at Silver Tree: A118 Studio Standard View

Oakland
  • Pool
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning
  • Gym
10.0 out of 10, Exceptional, (1)
The price is €236
includes taxes & fees
30 Nov - 1 Dec
Suites at Silver Tree: A118 Studio 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
  • Hot tub
9.6 out of 10, Exceptional, (5)
Mountain activities await at this lakeside retreat boasting both a heated pool and steaming hot tub. Kayaking, hiking, and skiing opportunities surround the property, while an arcade room and garden create perfect spaces for family entertainment.
The price is €416
includes taxes & fees
4 Dec - 5 Dec
In the heart of Deep Creek Lake! - "Shamrock Inn"
Indoor pool, a heated pool
Will O' The Wisp: 103A Efficiency/One Bath

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

Oakland
  • Indoor pool
  • Hot tub
9.6 out of 10, Exceptional, (8)
The price is €280
includes taxes & fees
4 Dec - 5 Dec
Will O' The Wisp: 103A Efficiency/One Bath
A heated pool
Cove Creek Lodge: 208 King Room ADA Accessible

Cove Creek Lodge: 208 King Room ADA Accessible

2.0 star property
Oakland
  • Pool
  • Free WiFi
  • Air conditioning
  • Game room
  • Parking available
  • Kitchen
10.0 out of 10, Exceptional, (4)
Refreshing heated pool waters await after exploring nearby caves, hiking trails, or kayaking adventures. Mountain enthusiasts appreciate this hotel's perfect blend of outdoor thrills and relaxing amenities, complete with poolside comfort.
The price is €265
includes taxes & fees
23 Nov - 24 Nov
Cove Creek Lodge: 208 King Room ADA Accessible
A heated pool
Cove Creek Lodge: 215 Standard Double Queen Room

Cove Creek Lodge: 215 Standard Double Queen Room

2.0 star property
Oakland
  • Pool
  • Free WiFi
  • Air conditioning
  • Game room
  • Parking available
  • Toys/games
10.0 out of 10, Exceptional, (2)
The price is €270
includes taxes & fees
23 Nov - 24 Nov
Cove Creek Lodge: 215 Standard Double Queen Room
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
  • Pool
  • Free WiFi
  • Air conditioning
  • Game room
  • Parking available
  • Toys/games
10.0 out of 10, Exceptional, (9)
Scenic mountain adventures unfold from the heated pool at Cove Creek Lodge, where families savour spacious fireplace rooms and kitchenettes. Beyond swimming, guests explore nearby Deep Creek Lake, kayaking, and rock climbing excursions.
The price is €263
includes taxes & fees
23 Nov - 24 Nov
Cove Creek Lodge: 210 Standard Double Queen Fireplace Room
A heated pool
Cove Creek Lodge: 214 Standard Double Queen Fireplace Room

Cove Creek Lodge: 214 Standard Double Queen Fireplace Room

2.0 star property
Oakland
  • Pool
  • Free WiFi
  • Air conditioning
  • Game room
  • Parking available
  • Toys/games
9.0 out of 10, Wonderful, (2)
Swimmers delight in the heated waters while adventure beckons beyond, with hiking trails, kayaking, and rock climbing nearby. After poolside relaxation, guests retreat to fireplace rooms with kitchenettes and private decks.
The price is €278
includes taxes & fees
4 Dec - 5 Dec
Cove Creek Lodge: 214 Standard Double Queen Fireplace Room
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
  • Pool
  • Free WiFi
  • Air conditioning
  • Game room
  • Parking available
  • Toys/games
10.0 out of 10, Exceptional, (5)
The price is €277
includes taxes & fees
23 Nov - 24 Nov
Cove Creek Lodge: 201 Poolside Double Queen Fireplace Room
Indoor pool, a heated pool
Will O' The Wisp: 107B One Bedroom/One Bath

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

Mountainside
  • Indoor pool
  • Hot tub
10.0 out of 10, Exceptional, (2)
Lakefront condo offers refreshing indoor pool access and soothing sauna facilities after exploring nearby hiking trails. Adventure seekers will appreciate the proximity to kayaking, rock climbing, and seasonal skiing opportunities.
The price is €301
includes taxes & fees
5 Dec - 6 Dec
Will O' The Wisp: 107B One Bedroom/One Bath
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 29 places to stay with pools. While you're visiting, you can explore sights such as Deep Creek Lake, and then take it easy poolside at one of the accommodation options in Oakland that travellers like for their pools.
What are some accommodation options with pools in Oakland?
The Garrett Inn: Cabin, 11-minute walk from Deep Creek Lake. Features kitchens, a communal pool and Smart televisions. Baja Motel: Holiday home, 5-minute walk from Deep Creek Lake. Offers kitchens, a communal pool and televisions.
How many hotels with pools will I 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?
Explore places such as Deep Creek Lake while you're in Oakland. Spend some time experiencing the great outdoors at Youghiogheny River and Broadford 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 the local weather in Oakland into account can help you maximise your time at the pool during your trip. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of 0°C. The snowiest months in Oakland are January, December, February and May, with each month seeing an average of 79 cm of snowfall.