Hotels with Swimming Pool in Highland Beach, Annapolis

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Highland Beach Hotels with Swimming Pool

Tonight
Jul 24 - Jul 25
Tomorrow
Jul 25 - Jul 26
This weekend
Jul 25 - Jul 27
Next weekend
Aug 1 - Aug 3

Top Highland Beach Hotels with Swimming Pool

Top Highland Beach Hotel Reviews

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"This place was clean and staff was nice. I also enjoyed the breakfast."
Leanna 3-night trip
Posted 2 days ago
Country Inn & Suites by Radisson, Annapolis, MD

Frequently asked questions

What are some hotels with pools in Highland Beach?
Historic Inns of Annapolis: Features buffet, an indoor pool, and free self parking. Graduate by Hilton Annapolis: Offers buffet, a seasonal outdoor pool, and free self parking. DoubleTree by Hilton Hotel Annapolis: Provides daily, a pool, and free self parking. Country Inn & Suites by Radisson, Annapolis, MD: Offers a snack bar/deli, an indoor pool, and daily. Annapolis Waterfront Hotel, Autograph Collection: Features complimentary wired internet access, an outdoor pool, and free self parking.
What is there to see and do in Highland Beach?
Make a point to visit attractions like Bay Ridge Beach and Annapolis Maritime Museum. Discover sights such as Maryland Quiet Waters Park, Annapolis Landing Marina, and Ego Alley during your stay.
When is the best time to book a hotel with a pool in Highland Beach?
You may want to consider a place to stay that offers an outdoor pool if you're planning to visit Highland Beach in the warmest months of July, August, or June when the average temp is 75°F. Lodging with an indoor pool may be the way to go if you visit during the coldest months of January, February, or December when the average temp is 40°F.