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Explore Chestertown
Red Roof Inn & Suites Chestertown offers free WiFi, free parking and coffee in the lobby. We're just minutes from Washington College, Chestertown Historic District, and Chestertown Marina. Need a suggestion for a nearby restaurant? Want some ideas of things to do for the whole family? Our front desk is always here to help! We are one of the best Chestertown budget hotels and are conveniently located at the crossroads of MD 213 and MD 291.
Stay in Comfort
Our pet friendly Inn & Suites features a designated pet area, coin laundry, and a snack center for your convenience. All guestrooms include flat screen TV's, a hairdryer, in-room coffee, microwave and refrigerator, and free expanded cable so you never have to miss your favorite shows. Book now! At Red Roof Inn & Suites Chestertown parking is free and bus/truck parking is available on a limited basis.
Boating on the Chester River
Sail along the picturesque Chester River from the Chestertown Marina. Or book a boat tour with Chester River Packet Company, which operates a 1920s style yacht, or Schooner Sultana, a replica of a 1768 British cutter that enforced Tea Taxes in the years leading up to the American Revolution.
Chestertown Historic District
Chestertown Historic District is home to more than fifty Georgian style townhomes, including the notable Hynson-Ringgold House, River House, and Widehall. Take a walking tour and don't forget to visit the Historical Society of Kent County to learn all about the history of Chestertown.
Get Married in Chestertown
Visiting wedding venues along Maryland's Eastern shore? Red Roof Inn Chestertown is close to Brittland Manor, Stepne Manor, The Bank, and Brampton Bed and Breakfast Inn.

100% Pet Friendly

At Red Roof Inn Chestertown, you stay happy and your pet stays free.

Chester River Packet Cruise

River Packet, a 65-foot classic yacht, offers charter dinner cruises on the scenic Chester River on Maryland’s Eastern Shore. This 1920-style tour boat, based in historic Chestertown, is a unique venue for both private events and public cruises.

RiverArts Gallery

RiverArt Gallery supports artists as a place to learn something new, share ideas, explore interesting topics, see and be seen, and meaningfully connect with friends, ideas, the local community, and the wider world.

Eastern Shore Food Lab

Promoting nourishing food for humans. The Eastern Shore Food Lab optimizes personal and community health by drawing upon the dietary past that built humans as a species. They research, reimagine, and share strategies that meet and exceed our biological and cultural needs. They transition culture by strengthening the ties between environment, society, family, and ourselves through food as they address issues of sustainability, food access, and dietary and social health.

Wine & Spirits

Wine and cocktail enthusiasts can look forward to unique experiences in Chestertown. Bad Alfred’s creates small-batch craft spirits in a former historic garage and filling station with a glassed-in distillery space, allowing patrons to watch the spirit-making process. Casa Carmen is a boutique family winery producing small-lot craft wines and vermouth. Sip wine and eat tapas in their tasting room, modeled after the traditional wine bodegas of Spain and South America.

Shop Locally

Visiting Chestertown on a Saturday? Visit the Chestertown Farmers & Artisans' Market at beautiful Fountain Park. Stroll through historic streets and visit local shops like Twigs & Teacups, The Bookplate, Riverside Unique, Angela's Cottage, Chestertown Electric and The Listening Room.

Chestertown Art

Art lovers should take their time exploring Chestertown's galleries. Massoni Art Gallery, Art on High, Chestertown RiverArts, Create, and Les Poissons Gallery house artworks by local and visiting artists. Or see a local production at the Garfield Center for the Arts at the Prince Theater.

Close to Campus

Visiting a loved one at Washington College? Red Roof Inn and Suites Chesterton is less than a mile away!

Eat Well, Sleep Well

- Beverly's Family Restaurant (0.11 mi)

- Arby's (0.25 mi)

- China House (0.19 mi)

- KFC (0.22 mi)

- Luisa's Cucina Italiana (0.18 mi)

- McDonald's (0.22 mi)

- Procolino's Pizza (0.19 mi)

- Taco Bell (0.22 mi)

- The FREEZE (0.18 mi)

- Domino's Pizza (0.40 mi)

Nearby Healthcare

University of Maryland Shore Medical Center at Chestertown is just 1.1 miles away and has state-of-the-art facilities dedicated to patient care, offering comprehensive healthcare.

"Amazing experience at this property, the rooms were spacious and maintained well , the staff are friendly and helpful, coming back soon ...thank you guys. The hotel is located in a peaceful environment and close to college and city center."

Chestertown