160 Scheeler Rd, Chestertown MD
Red Roof Inn & Suites Chestertown is one of the best budget hotels in Chestertown, MD that is conveniently located near the crossroads of MD 213 and MD 291.
We offer our guests free Wi-Fi, a guest coin laundry facility and free coffee in the lobby. Guests also have access to our designated pet area and free parking. Red Roof Inn & Suites Chestertown is a pet-friendly hotel where two well-behaved pets per room are welcome.
Check-in Age: 21 years or older (18 years or older with valid Military ID).
Pet Policy: One, well-behaved domestic pet (cat or dog) Stays Free! Pets must be declared at check-in. Up to 2 pets allowed per room. Second pet $15/ night, not to exceed 7 nights or $105 per pet per stay. Pet not to exceed 80 pounds. Service and emotional support animals are always welcome.
Deposit Policy: This location requires a $100 refundable deposit at check-in for incidentals.
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
RiverArts 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.
© 2025 Red Roof | All Rights Reserved.
© 2025 Red Roof | All Rights Reserved.
