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Weather Update

“Storms make trees take deeper roots. So the next time there's a hurricane in Orlando, come to Pigeon Forge.” — probably Dolly Parton

Weather Update

“Storms make trees take deeper roots. So the next time there's a hurricane in Orlando, come to Pigeon Forge.” — probably Dolly Parton

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Mar 4 - Mar 6 1 Room, 2 Guest
1-877-843-7663
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Rooms & Guests 1 Room, 1 Guest
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Red Roof Inn & Suites Chestertown, MD

Pet-Friendly Hotel Near Downtown Chestertown

Located near MD 213 and MD 291, Red Roof Inn & Suites Chestertown provides a convenient stay on Maryland’s Eastern Shore. Guests can enjoy easy access to downtown Chestertown, Washington College, and the Chester River waterfront.

Free Wi-Fi, complimentary lobby coffee, free parking, and a guest coin laundry provide practical amenities for everyday travel. A designated pet area also makes the hotel convenient for guests traveling with pets.

For campus visits, local events, outdoor activities, or a weekend in the area, this Chestertown, MD hotel offers a comfortable base close to key destinations.

With its accessible location and useful amenities, Red Roof Inn & Suites Chestertown makes it easy to settle in, recharge, and explore the surrounding area.

Front Office Phone
1-410-810-0555
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Enjoy the benefits of being a Red Roof member, from special rates to points you can redeem for future stays, adding value to your epic on-the-road adventure.

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Explore Chestertown Attractions

What’s Nearby

Enjoy convenient access to Washington College, Chestertown Marina, Sumner Hall, and Wilmer Park, with local museums and Chesapeake Farms Wildlife Habitat Tour also within easy reach.

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Discover Historic Chestertown Charm

Experience Chestertown’s History And Culture

Explore Chestertown through river cruises, historic landmarks, local art, and craft spirits. From waterfront adventures to cultural discoveries, the area offers plenty of ways to experience Maryland’s Eastern Shore.

View Travel Guides
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    Chester River Packet Company

    Cruise the Chester River aboard the Chester River Packet Company, offering a distinctive way to experience Chestertown’s waterfront and surrounding scenery from the water.

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    Chestertown RiverArts

    Connect with local creativity at Chestertown RiverArts, where art, ideas, community, and cultural experiences come together in the heart of Chestertown.

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    Bad Alfred’s Distillery

    Discover small-batch spirits at Bad Alfred’s, a craft distillery in a historic garage and filling station where visitors can experience the spirit-making process.

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    Historical Society Of Kent County

    Step into local history at the Historical Society of Kent County, where exhibits and collections offer insight into Chestertown and Kent County’s heritage.

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    Garfield Center For The Arts

    Enjoy performances and cultural programming at the Garfield Center for the Arts, a local destination that adds live entertainment and arts experiences to a Chestertown visit.

    Guest Reviews

    Quality
    Service
    Room

      Property Policies

      Check-in Age
      • 18 years and older.
      Deposit Policy
      • This location requires a $100 refundable deposit at check-in for incidentals.
      Pet Policy

        Frequently Asked Questions

        Contact

        • Red Roof Inn & Suites Chestertown allows guests who are 18 years or older to check in.

        • Yes. Red Roof Inn & Suites Chestertown requires a $100 refundable deposit at check-in for incidentals.

        • Yes. Red Roof Inn & Suites Chestertown offers free Wi-Fi for guests.

        • Yes. Red Roof Inn & Suites Chestertown offers free parking.

        • Yes. One well-behaved domestic cat or dog stays free. Up to two pets are allowed per room. The second pet costs $15 per night, limited to 7 nights or $105 per pet per stay. Pets must be declared at check-in and cannot exceed 80 pounds. Service and emotional support animals are always welcome.

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        Meet the New Red Roof App

        Travel made simple—book, manage, and save with exclusive rates. Plus, earn 500 bonus RediRewards points when you book in the app.
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