Located in the heart of Chestertown, Red Roof Inn & Suites offers a welcoming retreat with laundry facilities and a cozy fireplace. Connect to WiFi, grab a cup of coffee from the lobby, and enjoy extended parking. The helpful staff has left guests feeling supported during their stay.
Chestertown Historic District - 2 min drive - 2.8 km
Historical Society of Kent County Maryland - 2 min drive - 2.8 km
River Arts Chestertown - 3 min drive - 3.1 km
Getting around
Easton, MD (ESN-Easton - Newnam) - 51 min drive
Baltimore Washington Intl. Airport (BWI) - 80 min drive
Baltimore, MD (MTN-Martin State) - 106 min drive
Restaurants
Milano's Pizzeria - 5 min drive
McDonald's - 9 min walk
Dunkin - 3 min walk
Royal Farms - 5 min drive
Procolino's - 9 min walk
About this property
Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown is a great choice for a stay in Chestertown. You'll have free perks like WiFi and self parking. Fellow travelers love the helpful staff.
At a glance
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Hotel size
53 rooms
Arranged over 3 floors
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Arriving/Leaving
Check-in start time: 3 PM; Check-in end time: anytime
Minimum check-in age: 21
Check-out time is 11 AM
Contactless check-out available
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Special check-in instructions
Front desk staff will greet guests on arrival at the property
Information provided by the property may be translated using automated translation tools
This property allows guests 18 or over to check in with valid military ID.
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Required at check-in
Credit card, debit card, or cash deposit required for incidental charges
Government-issued photo ID may be required
Minimum check-in age is 21
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Children
Up to 3 children (17 years old and younger) stay free when occupying the parent or guardian's room, using existing bedding
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Pets
Pets allowed (dogs and cats only, 2 total, up to 80 lbs per pet)*
Service animals welcome
Restrictions apply*
Pets must be supervised
WIFI
Internet
Free WiFi in public areas
Free WiFi in rooms
LOCAL_PARKING
Parking
Free uncovered onsite self parking
Free onsite RV/bus/truck parking
Wheelchair-accessible parking on site
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Other information
Designated smoking areas
Property amenities
Food and drink
Coffee/tea in a common area
Traveling with children
Children stay free (see details)
Services
24-hour front desk
Laundry facilities
Free newspapers in lobby
Facilities
1 building/tower
Built in 1996
Fireplace in lobby
Television in common areas
Accessibility
Elevator
Wheelchair-accessible path of travel
Wheelchair-accessible parking
Wheelchair-accessible path to elevator
Wheelchair-accessible registration desk
Lever door handles
Well-lit path to entrance
Room amenities
Be entertained
43-inch flat-screen TV
Premium cable channels
Pay movies
Home comfort
Air conditioning and heating
Coffee/tea maker
Iron/ironing board
Sleep well
Blackout drapes/curtains
Free crib/infant bed
Bed sheets provided
Freshen up
Private bathroom
Free toiletries
Hair dryer
Towels
Toilet paper
Stay connected
Desk
Free WiFi
Free long-distance and local calls
Desk chair
Food and drink
Mini-fridge
Microwave
More
Daily housekeeping
Fees & policies
Refundable deposits
Deposit: USD 100.00 per accommodation, per stay
Pets
Service animals exempt from fees
Pets are allowed for an extra charge of USD 15 per pet, per night (maximum USD 105 per stay)
Policies
Noise-free guestrooms cannot be guaranteed.
This property welcomes guests of all sexual orientations and gender identities (LGBTQ+ friendly).
This property accepts credit cards. Cash is not accepted.
Credit cards accepted: Visa, Mastercard, American Express, Discover
Please note that cultural norms and guest policies may differ by country and by property. The policies listed are provided by the property.
Daily housekeeping is included for stays of 6 nights or less. Limited housekeeping is provided for stays of 7 nights or more.
Pets must be declared at check-in. Guests bringing 1 pet will not be charged pet fees. The listed pet fee in the Fees section applies only if guests bring 2 or more pets. Pets must be leashed in public areas of the property. Guests are expected to clean up after their pet.
Also known as
Comfort Suites Chestertown
Comfort Suites Hotel Chestertown
Comfort Hotel Chestertown
Quality Suites Hotel Chestertown
Quality Suites Chestertown
Quality Suites
Red Roof & Suites Chestertown
Red Roof Inn & Suites Chestertown Hotel
Red Roof Inn & Suites Chestertown Chestertown
Red Roof Inn & Suites Chestertown Hotel Chestertown
Frequently asked questions
Are pets allowed at Red Roof Inn & Suites Chestertown?
Yes, cats and dogs are welcome, with a limit of 2 total and maximum weight of 80 lbs per pet. There's a charge of USD 15 per pet, per night. Service animals are exempt from fees. Some restrictions may apply, so please contact the property for more details.
Is parking offered on site at Red Roof Inn & Suites Chestertown?
Yes, there's free self parking. Free RV/bus/truck parking is available.
What are the check-in and check-out times at Red Roof Inn & Suites Chestertown?
Check-in start time: 3 PM; Check-in end time: anytime. Check-out time is 11 AM. Contactless check-out is available.
What's the area around Red Roof Inn & Suites Chestertown like?
Red Roof Inn & Suites Chestertown is in the heart of Chestertown, a short 11-minute walk from Washington College and 19 minutes' walk from Chestertown Dog Park.
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Reviews
Red Roof Inn & Suites Chestertown Reviews
7.2
Good
All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
7.4
Cleanliness
8.6
Location
7.8
Staff & service
6.6
Property conditions & facilities
Popular mentions
Room
Service staff
Bathroom
Breakfast
Couch
Shower
Bed
Lobby
Coffee
Desk
Reviews
Verified
10/10 Exceptional
Jan 16, 2026
Arrived earlier than expected and the staff was very accommodating and friendly which made for an excellent stay from start to finish.
Linette
Linette, 1-night trip
Verified
8/10 Very good
Jan 2, 2026
Clean and friendly staff. Good location.
Robert
Robert, 1-night trip
Verified
10/10 Exceptional
Mar 23, 2026
Stay was great. Booked 3 rooms for a family event. Check in was great and the staff was awesome. My room out of the 3 had an issue with the AC/heat. I explained the issue the next morning and when realizing they couldn’t fix the issue they were able to put us in another room. Very kind and professional.
Tim
Tim, 2-night trip
Verified
8/10 Very good
Dec 1, 2025
Professional staff, warm greetings clean room
Dr. Nicholas and Mrs. Karen
Dr. Nicholas and Mrs. Karen, 4-night trip
Verified
10/10 Exceptional
Oct 6, 2025
Wish they had the pool open. The staff is great here and very helpful.
lisa
lisa, 2-night trip
Verified
10/10 Exceptional
May 19, 2025
Very nice location and area
Vicente
Vicente, 1-night trip
Verified
10/10 Exceptional
Apr 20, 2025
Easy to get to, food all around!
Gary
Gary, 1-night trip
Verified
10/10 Exceptional
Sep 27, 2025
Room temperature was good. Room was also very spacious and clean.
Kellie
Kellie, 1-night trip
Verified
10/10 Exceptional
Oct 10, 2025
Well received by front desk attendant. Clean room!
Federico
Federico, 1-night trip
Verified
10/10 Exceptional
Aug 12, 2024
Nice place to stay
Staff were very kind. Easy parking and comfortable rooms.
April
April, 2-night trip
Verified
8/10 Very good
Nov 6, 2024
Staff was very friendly
Matthew
Matthew, 1-night trip
Verified
10/10 Exceptional
Sep 1, 2025
Time to upgrade the furniture in the rooms. The staff is doing a GREAT JOB cleaning and providing excellent service.
lisa
lisa, 1-night trip
Verified
10/10 Exceptional
Jan 21, 2025
Have stayed here several times. Nice staff and clean rooms. Can walk for food
DAMEION
DAMEION, 1-night trip
Verified
10/10 Exceptional
Aug 14, 2023
Great Place
Amazing stay. Wonderful hotel, comfortable beds, very clean. Super nice staff.
April
April, 2-night trip
Verified
8/10 Very good
May 31, 2024
We have stayed here many times before and I was able to book a one night stay for our quick trip this time. Very comfortable and relaxing, rooms are nice
Shannon
Shannon, 1-night trip
Verified
10/10 Exceptional
Oct 29, 2023
Excellent value for the price. Accessible location, very quiet, clean, everything we needed was in our rooms.
Bonney
Bonney, 2-night trip
Verified
6/10 Good
Oct 14, 2025
The rug was old and dirty. There were stains on the small sofa. The cleaning staff was consistent with their work and kept fresh towels and cleaned up nicely for which we left them a nice tip in reciprocity. However, the place should be renovated completely out of common courtesy to the customers who pay good money to stay there.
Richard C
Richard C, 3-night trip
Verified
6/10 Good
Oct 25, 2023
Reception staff was friendly and helpful.
James
James, 3-night trip
Verified
10/10 Exceptional
Oct 29, 2023
Good stay
Staff was very pleasant and helpful
Terry dian
Terry dian, 1-night trip
Verified
10/10 Exceptional
May 29, 2024
nice hotel. helpful staff. stores and dining are walkable distances.
alaiyah
alaiyah, 4-night trip
Verified
10/10 Exceptional
Nov 5, 2023
Great room and stay!
Our stay was great! We were coming into town to see family and needed a place to stay. It worked out perfectly.
Laura
Laura, 1-night trip
Verified
8/10 Very good
Oct 21, 2024
A little rough around the edges in some ways, but the rooms were large, quiet, and clean.
Craig
Craig, 1-night trip
Verified
10/10 Exceptional
Nov 22, 2023
Have stayed here several times. Is safe and clean. Walking distance to dining.
DAMEION
DAMEION, 1-night trip
Verified
4/10 Fair
Jul 20, 2025
The facility is tired and dated. Needs new carpets in the halls, upgraded amenities in the Bathroom, new furniture in the room and decent sized pillows.
Peter
Peter, 1-night trip
Verified
6/10 Good
Sep 17, 2023
Property is old and tired, but staff was especially polite and helpful.