Photo by Patricia Knorr

Find Hotels with a Pool in Chester, MD

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Pick from Chester Hotels with a Pool and compare room rates, reviews, and availability. Most hotels are fully refundable.

Frequently asked questions

What are some hotels with pools in Chester?
Historic Inns of Annapolis: Features buffet, a seasonal outdoor pool, and complimentary wireless internet access. Graduate by Hilton Annapolis: Hotel located near U.S. Naval Academy. Provides a full-service spa, an indoor pool, and a snack bar/deli. Hilton Garden Inn Annapolis Downtown: Features buffet, an indoor pool, and free self parking. Crowne Plaza Annapolis, an IHG Hotel: Offers a snack bar/deli, an indoor pool, and daily. DoubleTree by Hilton Hotel Annapolis: Provides a snack bar/deli, an indoor pool, and free self parking.
What is there to see and do in Chester?
Enjoy a stroll along the shore at Sandy Point Beach and Downs Park Dog Beach. Discover sights such as Chesapeake Bay Environmental Center, Eastern Neck National Wildlife Refuge, and Queenstown Harbor Golf Club during your stay.
When is the best time to book a hotel with a pool in Chester?
You may want to think about a place to stay with an outdoor swimming pool if you plan to visit Chester in the warmest months of July, August, or June when the average temperature is 74°F. Lodging offering an indoor pool may be the way to go if you are visiting during the coldest months of January, February, or December when the average temp is 39°F.