Photo by KM Moore

Find Hotels with a Pool in Oakland, MD

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Top Oakland Hotels with a Pool

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until December 4 with our Black Friday deals. Stay by December 15, 2025.
Unlock Black Friday deals

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 76 places to stay with pools. During your trip, you can explore sights such as Deep Creek Lake and Deep Creek Lake 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: Vacation home located near Deep Creek Lake. Offers complimentary wireless internet access, a communal pool, and kitchens. Dog-friendly cabin with private hot tub, Ping-Pong & lake views: Vacation home located near Deep Creek Lake. Provides kitchens, a communal pool, and televisions.
How many pool hotels will I be able to find in Oakland?
Expedia’s 76 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 Swallow Falls State Park and Youghiogheny River. 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.