Photo by Patricia Knorr

Find Hotels with a Pool in Chester, MD

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Check availability on Chester Hotels with a Pool

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

Frequently asked questions

What are some hotels with pools in Chester?
Graduate by Hilton Annapolis: Features a snack bar/deli, an indoor pool, and daily. Crowne Plaza Annapolis, an IHG Hotel: Hotel located near U.S. Naval Academy. Offers a full-service spa, an indoor pool, and a snack bar/deli. DoubleTree by Hilton Hotel Annapolis: Features a snack bar/deli, an indoor pool, and free self parking. Historic Inns of Annapolis: Offers daily, a seasonal outdoor pool, and complimentary wired internet access. Hilton Garden Inn Annapolis Downtown: Features buffet, 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 Bay Ridge Beach. Discover sights such as Matapeake State Park, Love Point State Park, and Eastern Neck National Wildlife Refuge 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.