Free Wi-Fi
Elevator / Lift
Designated Smoking Area
Vending Machines
24-Hour Front Desk
Coffee/Tea in Common Areas
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Based on 457 verified reviews
AI-generated summary based on recent guest reviews
Dom
Apr 26, 2026
·
Stayed 1 night
Lisa
Apr 24, 2026
·
Stayed 1 night
Lisa
Apr 7, 2026
·
Stayed 2 nights
Kevin
Mar 23, 2026
·
Stayed 1 night
Tim
Mar 23, 2026
·
Stayed 2 nights
A stay at Red Roof Inn & Suites Chestertown places you in the heart of Chestertown, within a 5-minute drive of Washington College and Larrabee Arts Center. This hotel is 0.8 mi (1.3 km) from Rolling Road Park and 0.9 mi (1.4 km) from Chestertown Dog Park.
Washington College(0.5 miles)
Rolling Road Park(0.9 miles)
Larrabee Arts Center(1 miles)
Chestertown Dog Park(1 miles)
Historical Society of Kent County Maryland(1.6 miles)
Wilmer Park(1.7 miles)
Check-in
Check-out
From 15:00 to 23:59
Before 11:00
Free self-parking is available on-site, including designated parking for RVs, buses, and trucks. The parking is uncovered.
Pets are allowed, with no charge for one pet. A fee of $15 per additional pet per night applies, with a maximum fee of $105 per stay. Service animals are exempt from fees.
Check-in is at 3:00 PM and check-out is at 11:00 AM. Early or late check-in/check-out may be available upon request, but additional charges may apply.
The hotel offers several accessibility features including a wheelchair-accessible registration desk, limited wheelchair-accessible rooms, elevators, and well-lit paths to the entrance.
The hotel is located in the heart of Chestertown, within a 5-minute drive of Washington College and Larrabee Arts Center. It is 0.8 miles from Rolling Road Park and 0.9 miles from Chestertown Dog Park.
Up to 3 children aged 17 years and younger can stay free when occupying the parent or guardian's room, using existing bedding.
Instant AI responses are based on hotel information