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Red Roof Inn & Suites Chestertown

2.0 star property
Hotel perfectly located for exploring Chestertown

Choose dates to view prices

Photo gallery for Red Roof Inn & Suites Chestertown

Lobby lounge
Lobby lounge
Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board
Exterior
Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board

Reviews

7.2 out of 10
Good

Popular amenities

  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Laundry
  • Housekeeping

Explore the area

View in a map
160 Scheeler Rd, Chestertown, MD, 21620
  • Place, Washington College
    ‪8 min walk‬
  • Place, Historical Society of Kent County Maryland
    ‪3 min drive‬
  • Place, River Arts Chestertown
    ‪3 min drive‬
  • Airport, Baltimore, MD (MTN-Martin State)
    ‪105 min drive‬

Room options

View all photos for Superior Room, 1 King Bed, Accessible, Non Smoking

Desk, laptop workspace, blackout drapes, iron/ironing board

Superior Room, 1 King Bed, Accessible, Non Smoking

8.6 out of 10
Excellent
(9 reviews)
  • 419 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed

View all photos for Superior Room, 1 King Bed, Accessible, Non Smoking

Desk, laptop workspace, blackout drapes, iron/ironing board

Superior Room, 1 King Bed, Accessible, Non Smoking

7.6 out of 10
Good
(11 reviews)
  • 425 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed

View all photos for Standard Suite, 1 King Bed with Sofa bed, Non Smoking

Desk, laptop workspace, blackout drapes, iron/ironing board

Standard Suite, 1 King Bed with Sofa bed, Non Smoking

7.0 out of 10
Good
(18 reviews)
  • 419 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Suite, Multiple Beds, Non Smoking

Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board

Suite, Multiple Beds, Non Smoking

8.4 out of 10
Very good
(17 reviews)
  • 450 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed

About the neighborhood

Chestertown

Heart of Chestertown.Stay at this Chestertown hotel and you'll be within half a mile (1 km) of Washington College and 2 miles (3 km) of Rolling Road Park. Chestertown Dog Park and Historical Society of Kent County Maryland are also within 2 miles (3 km).

What's nearby

  • Washington College - 8 min walk - 0.4 miles
  • Chestertown Dog Park - 17 min walk - 0.9 miles
  • Historical Society of Kent County Maryland - 3 min drive - 1.7 miles
  • Garfield Center for the Arts at the Prince Theater - 3 min drive - 1.7 miles
  • River Arts Chestertown - 3 min drive - 1.7 miles

Getting around

  • Baltimore Washington Intl. Airport (BWI) - 80 min drive

Restaurants

  • ‪Milano's Pizzeria - ‬5 min drive
  • ‪Royal Farms - ‬5 min drive
  • ‪Dunkin - ‬3 min walk
  • ‪McDonald's - ‬9 min walk
  • ‪Royal Farms - ‬2 min drive

About this property

Red Roof Inn & Suites Chestertown

Hotel perfectly located for exploring Chestertown
As a guest of Red Roof Inn & Suites Chestertown, you'll find a vending machine, coffee/tea in a common area, and complimentary newspapers in the lobby. WiFi is free in public spaces. Red Roof Inn & Suites Chestertown also features a fireplace in the lobby, laundry facilities, and an elevator. Self parking is free.

Smoking is allowed in designated areas at this Chestertown hotel.

  • 1 building
  • 53 guestrooms or units
  • 3 levels
  • Built in 1996
  • Coffee in lobby
  • Self-service laundry
  • Front desk (24 hours)
  • Newspapers in lobby (free)
  • Fireplace in lobby
  • Television in lobby
  • Elevator
  • Smoking in designated areas
Red Roof Inn & Suites Chestertown offers 53 air-conditioned accommodations with coffee/tea makers and hair dryers. 43-inch flat-screen televisions come with premium cable channels and pay movies.

This Chestertown hotel provides complimentary wireless Internet access. Business-friendly amenities include desks and desk chairs; local and long-distance calls are complimentary (restrictions may apply). Additionally, rooms include irons/ironing boards and complimentary toiletries. Change of towels and change of bedsheets can be requested. Housekeeping is provided daily.

Similar properties

Free daily full breakfast
Comfort Inn & Suites Chestertown
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
4.3 out of 5, Excellent, 879 reviews
$101 nightly
The price is $112
Mar 8 - Mar 9
Total with taxes and fees
Comfort Inn & Suites Chestertown

Property amenities

Family friendly

  • In-room crib
  • In-room microwave
  • Laundry facilities
  • Mini-fridge

Internet

  • Available in all rooms: Free WiFi
  • Available in some public areas: Free WiFi

Parking and transportation

  • Free uncovered self parking on site
  • Free RV/bus/truck parking on site
  • Wheelchair-accessible parking available

Food and drink

  • Coffee and tea in common areas

Things to do

  • TV in common areas

Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Elevator
  • Lever door handles
  • Well-lit path to entrance
  • Wheelchair accessible (may have limitations)
  • Wheelchair-accessible parking
  • Wheelchair-accessible path of travel
  • Wheelchair-accessible path to elevator
  • Wheelchair-accessible registration desk

Room amenities

Entertainment

  • 43-inch flat-screen TV with premium cable channels
  • Pay movies

Bedroom

  • Bedsheets provided
  • Blackout drapes
  • Free crib

Bathroom

  • Free toiletries
  • Hair dryer
  • Private bathroom
  • Shampoo
  • Soap
  • Toilet paper
  • Towels provided

Food and drink

  • Coffee/tea maker
  • Microwave
  • Mini-fridge

More

  • Air conditioning
  • Desk
  • Desk chair
  • Free local calls
  • Free long-distance calls
  • Heating
  • Iron/ironing board
  • Laptop workspace

Policies

Check-in

Check-in start time: 3 PM; Check-in end time: anytime
Minimum check-in age: 21

Check-out

Check-out before 11 AM
Contactless check-out available

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.

Access methods

Staffed front desk

Pets

  • Pets: USD 15 per pet, per night (maximum USD 105 per stay)
  • Only dogs and cats are allowed
  • Maximum 2 (weight limit: 80 lbs per pet)
  • Pets cannot be left unattended
  • Restrictions apply
  • For more information, you can reach out to the property at the number on the booking confirmation
  • Service animals are exempt from fees

Children and extra beds

  • Children are welcome.
  • Kids stay free! Up to 3 children 17 years old and younger stay free when using existing bedding.
  • Rollaway/extra beds are not available.
  • Free cribs (infant beds)!

Property payment types

Important information

Fees

Guests will be asked to pay the following charges at the property:

  • Deposit: USD 100.00 per accommodation, per stay

We've listed all charges provided to us by the property.

Optional extras

The fees and deposits listed below will be charged at the time of service, check-in, or check-out.

  • Pet fee: USD 15 per pet, per night (maximum USD 105 per stay)
  • Service animals are exempt from fees

This may not be a comprehensive list. Fees and deposits are subject to change and might not include tax.

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts credit cards; cash is not accepted
Noise-free guestrooms cannot be guaranteed
Please note that cultural norms and guest policies may differ by country and by property; the policies listed are provided by the property
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. This property accepts Visa, Mastercard, American Express, and Discover. Cash is not accepted. Noise-free guestrooms cannot be guaranteed.

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.

We should mention

  • Up to 3 children 17 years old and younger stay free in the same room as the parent or guardian when using existing bedding.
  • To make arrangements to bring your pet, contact the property directly at the number on your booking confirmation (please see the Fees section for related charges).
  • This property welcomes guests of all sexual orientations and gender identities (LGBTQ+ friendly).

Property is 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

How close is Red Roof Inn & Suites Chestertown to the airport?

Red Roof Inn & Suites Chestertown is 77.3 mi (106-min drive) away from the Baltimore, MD (MTN-Martin State) airport, the closest popular airport to the property.

How much does it cost to stay at Red Roof Inn & Suites Chestertown?

As of Feb 27, 2026, prices found for a 1-night stay for 2 adults at Red Roof Inn & Suites Chestertown on Feb 28, 2026 start from 80.0, excluding taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Does Red Roof Inn & Suites Chestertown have an airport shuttle?

Airport shuttle services are not available at Red Roof Inn & Suites Chestertown.

How close is Red Roof Inn & Suites Chestertown to the beach?

This hotel is 11.9 mi (19-min drive) from Betterton Beach and 12.5 mi (24-min drive) from Main Beach. Don't forget your sunscreen!

Does Red Roof Inn & Suites Chestertown offer free breakfast?

Red Roof Inn & Suites Chestertown does not offer free breakfast.

Is there a casino at Red Roof Inn & Suites Chestertown?

No, there is no casino at this hotel.

What time is check-in at Red Roof Inn & Suites Chestertown?

Check-in start time: 3 PM; Check-in end time: anytime.

Is there free parking at Red Roof Inn & Suites Chestertown?

This hotel offers free self parking.

Does Red Roof Inn & Suites Chestertown have a pool?

Red Roof Inn & Suites Chestertown does not have a pool.

Does Red Roof Inn & Suites Chestertown have a spa?

There are no spa services available at this hotel.

How close is Red Roof Inn & Suites Chestertown to downtown Chestertown?

Red Roof Inn & Suites Chestertown is 0.6 mi away from Chestertown.

Red Roof Inn & Suites Chestertown Reviews

Reviews

7.2

Good

Rating 10 - Excellent. 125 out of 427 reviews
Rating 8 - Good. 129 out of 427 reviews
Rating 6 - Okay. 83 out of 427 reviews
Rating 4 - Poor. 54 out of 427 reviews
Rating 2 - Terrible. 36 out of 427 reviews

7.4/10

Cleanliness

7.8/10

Staff & service

5.6/10

Amenities

6.8/10

Property conditions & facilities

Reviews

10/10 Excellent

Vincent

Liked: Cleanliness, staff & service, amenities
room was clean but the shower curtain was in tatters. multiple rings torn off
Stayed 1 night in Nov 2025

6/10 Okay

Milo M

Traveled with group
Liked: Staff & service
Disliked: Cleanliness, amenities
I stayed for two nights, Sat-Mon (Nov. 2025) and was overall disappointed with my stay at Red Roof Inn & Suites in Chestertown, MD. The two women at the front desk were professional and friendly. The following are the issues I had during my stay: - During all times of the day, there were what seemed to be day laborers hanging out in the parking lot. At night, I could hear them speaking and playing their "boom boom" music when all I wanted was to go to sleep. - The elevator smelled of a dirty ash tray. (I went across the street to Acme and bought air freshner to try to kill the odor. - Once I entered my room, I noticed wallpaper peeling away from the wall in three different places. Two of the lamp shades were hanging off the lamp. It seems screws were missing. The handle on the nightstand was hanging off as there was a screw missing. There was also a circular splash/spill mark on the wall above the desk. To clean it up, I used one of the washcloths in the bathroom. - The toilet would not flush! I attempted to fix it, as I've done at home several times before, but was unable to resolve the issue. I asked one of the two women to move to a different room as there were two of us staying in the room, but I was advised that all the other rooms with king sized beds were booked for the weekend. POSITIVE: - The king size bed was very comfortable and the pillows smelled clean and were also equally comfortable. - The cost was better than Comfort Inn & Suites, but....
Stayed 2 nights in Nov 2025

8/10 Good

Matt

Stayed 1 night in Nov 2025

4/10 Poor

Bryan

Traveled with family
Disliked: Property conditions & facilities
Room had broken bathroom doorknob, stained carpet and smelled lightly of smoke. Lobby smelled strangely.
Stayed 1 night in Nov 2025

2/10 Terrible

Elizabeth

Disliked: Cleanliness, staff & service, amenities, property conditions & facilities
I checked in and have never felt less welcome in a hotel. The lobby space was dingy and sad. Then the hallway on the third floor leading to my room stank of cigarettes and looked about as creepy as the shining, and it was afternoon. The room itself was pitch black when I entered, the blackout curtains drawn, and even with the front door light on it was so dark that I bumped into a coffee table I couldn't see, and finally reached the window to let in some light. The room also smelled of cigarettes, and there was a hair on the pillow. None of this would have mattered to me at $94 a night, but then at 3am some jerks a few rooms away got home from the bars I guess, and I was subjected to pumping bass from that time until 8:45 am, when my 4th call to the front desk finally put something in motion that got it to stop, so I could get a 20 minute cat nap. The front desk (2 different people) was neither effective nor helpful for the most part, and I ended up spending the second prepaid night through Expedia on a friend's futon and got such better sleep. I want a full refund, and neither Expedia nor the hotel seem to want to cooperate.
Stayed 2 nights in Nov 2025

10/10 Excellent

Derek

Liked: Cleanliness, staff & service
Disliked: Property conditions & facilities
This property was clean but dated. The carpet was stained, the furniture and fixtures were worn and broken, towels were washed but old and in need of replacement.
Stayed 1 night in Nov 2025

6/10 Okay

Mary

Traveled with group
Disliked: Amenities, property conditions & facilities
Bathroom floor not completely clean. Difficulty with lights. No interaction with staff except receptionist at the front desk.
Stayed 1 night in Nov 2025

6/10 Okay

Pamela

Traveled with family
Liked: Cleanliness
Disliked: Amenities
The room had some "repairs' that were not finished. It was clean but did not smell fresh. The price was right, though.
Stayed 2 nights in Oct 2025

8/10 Good

Jason

its an average hotel with a clean bed to sleep in
Stayed 1 night in Oct 2025

10/10 Excellent

Dana

Stayed 1 night in Oct 2025

2/10 Terrible

Ramon I, Vienna

Traveled with family and small children
Disliked: Cleanliness, staff & service, property conditions & facilities
Not clean. Staff not friendly.
Stayed 2 nights in Oct 2025

6/10 Okay

Richard C

Liked: Cleanliness, room comfort
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.
Stayed 3 nights in Oct 2025

6/10 Okay

Allen, Bear

Traveled with group
Liked: Staff & service
Disliked: Cleanliness
Food stains on the carpets, spots throughout the carpets in commons and in rooms.
Stayed 1 night in Oct 2025

8/10 Good

Lynn

Stayed 1 night in Oct 2025

10/10 Excellent

lisa

Traveled with group
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Wish they had the pool open. The staff is great here and very helpful.
Stayed 2 nights in Oct 2025

4/10 Poor

Johann

Disliked: Cleanliness, property conditions & facilities
TV and fridge did not work on arrival.
Stayed 2 nights in Sep 2025

4/10 Poor

Nancy

Traveled with family
Disliked: Cleanliness, staff & service, amenities, property conditions & facilities
Staff was not welcoming or accommodating. Very dirty facility, not only the rooms but communal areas. Very outdated decor and furnishings. Should not be charging over $100 er night for such accommodations.
Stayed 1 night in Sep 2025

10/10 Excellent

Kellie

Traveled with group
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Room temperature was good. Room was also very spacious and clean.
Stayed 1 night in Sep 2025

8/10 Good

kendall

Stayed 1 night in Sep 2025

8/10 Good

Ron

Stayed 1 night in Sep 2025

8/10 Good

Todd

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Sep 2025

6/10 Okay

Angela

Stayed 1 night in Sep 2025

2/10 Terrible

Sonny

Disliked: Cleanliness, property conditions & facilities
worn out carpet, damaged furniture. bug in the bed ect...
Stayed 1 night in Sep 2025

4/10 Poor

Verified traveler

Disliked: Cleanliness, property conditions & facilities
The room was very dated. Cigarette burn on comforter. Towel rack in bathroom was hanging off the wall and ceiling had a gaping hole where a light should be. Will not be going back.
Stayed 1 night in Sep 2025

8/10 Good

Zachary

Stayed 1 night in Aug 2025