Find & compare golf resorts in Chestertown, MD

Fore! Feel like a winner of the Masters knowing you can easily book a great selection of Chestertown golf resorts! Whether you’re a rookie or a golf prodigy, you’ll be teeing off on your favorite green in no time. The golf hotels in Chestertown allow you to enjoy all the benefits of staying close to the premier golf courses in the area.

Improve your game by working on your backswing, stance, and grip at the driving range before heading to the fairway for a bout on the back nine. Impress a business prospect on the executive course or enjoy a delightful day on the fairway with your family and friends, then head back to one of the best golf resorts in Chestertown for cocktails or dinner. Relax in your home away from home, knowing you’re bound to hit a hole-in-one with your hotel—though you still may need to work on your short game.

From 5-star amenities to budget lodging, Travelocity offers a variety of golf resorts in Chestertown to suit your every need. We can’t guarantee you’ll hit a double eagle on the course, but we will guarantee our prices. Book with Travelocity and your hotel will be on par, so you won’t bogey on your next golf adventure.