Find & compare hotels with pools in Chestertown, MD from $70 total

Whether you’re traveling for vacation or business, nothing says “relaxation” quite like floating on an inflatable raft. For water-lovers like you, finding a hotel with a pool in Chestertown is a must-do on the itinerary. From cannonballs to gentle wading, Travelocity will help you snag the perfect hotel so you can cool off however you need to.

Booking hotels in Chestertown with a pool doesn’t mean you have to sacrifice your room amenities, either. You’ll still receive the same tender loving care from the friendly staff, fresh towels to dry off with, and tasty room service at your beck and call.

Chestertown hotels with a pool are perfect for everyone from a solo traveler looking to get some exercise first thing in the morning to a big family who needs to keep the kiddos entertained. Many of these accommodations also offer a hot tub, so you can soak away any stress in the warm bubbles.

If you’re worried about prices, Travelocity won’t leave your wallet hanging out to dry. Book your hotel with us and rely on the Travelocity Price Guarantee to get the most affordable rates. You’ll soon be splashing around and exploring a new city, all from the home base of an affordable hotel.