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Chestertown Bed and Breakfasts & Inns

Whether you want to attend a fun festival, dive into early American history, or just relax and unplug, the quaint town of Chestertown, MD, is the perfect weekend getaway.

Welcome to Chestertown, MD

Are you in need of a good dose of rest and relaxation? Pack your suitcase and head to historic Chestertown, MD. Founded in 1706, this adorable town is full of history and charm located right outside of Chesapeake Bay. Chestertown is right on the edge of the Chester River and there’s enough to do here to keep you busy throughout your vacation. However, it’s also a great spot to unplug, which means you can achieve full relaxation and rejuvenation. Enjoy a steaming cup of coffee as you wander the Chestertown Marina and watch the stunning British Royal Navy replica, Sultana, glide through the fog-laden waters to the dock. Meander the Chestertown downtown area, a foodie and boutique shopping enthusiast’s paradise. If you’re looking for excitement, Chestertown is home base for many fun festivals throughout the year. Plan your next trip here and allow Select Registry to help you find the best bed and breakfast in Chestertown! 

Things to See & Do

There is so much to see and do in Chestertown! Begin with a walk through the town’s waterfront area and downtown. Visitors can pick up a map and check out a 30-minute, self-guided audio tour. The map will lead you through the charming downtown and gorgeous Colonial homes that are still in pristine condition.Stick around the waterfront and check out Sultana, the British Navy replica ship. The ship offers two-hour public cruises along the Chester River. The Sultana was completed in 2001 and is an incredible step into the past. Passengers on the boat can raise the sails, steer the boat and see the quarters below. The water also offers a distinct vantage point for the beautiful town and shoreline. It’s worth the visit!

Where to Eat & Drink

As a food lover's paradise, you can get everything you can imagine and more in Chestertown. This is a town that truly embraces the idea of farm-to-table, so plan to tour one of the local farms and then eat the bounty at one of the many restaurants serving the fare! From bistros to taverns to coffeehouses offering the best pastries you’ve ever tasted, Chestertown can satisfy every appetite. On Saturday mornings, check out the Chestertown Farmers Market for the best selection of fruits, vegetables, cheeses, meats, and so much more.

Best Time to Visit

With year-round events and festivals, there is no bad time to visit Chestertown! In the spring, take part in Paint the Town, a three-day event held every April. Summertime brings the Tea Party Festival, the National Music Festival and the 4th of July celebrations. Fall is absolutely stunning in Chestertown, as nature paints itself in fall glory! In the winter, the town is often blanketed in pristine snow. Catch the Holiday House Tour and the Winterfest Weekend activities every weekend through December.

Where to Stay

Your getaway to the enchanting and historic Chestertown begins when you choose one of our incredible bed and breakfasts. Choose from our different locations as your home away from home. Our Chestertown bed and breakfasts are conveniently located and come with our top-of-the-line amenities, services and incredible breakfasts to get your time on Maryland's eastern shore started off on the right foot. Be sure to check out our selections below and book your favorite today.

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