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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

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

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, Chestertown Dog Park
    ‪17 min walk‬
  • Place, Historical Society of Kent County Maryland
    ‪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
  • 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
  • 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
  • Rolling Road Park - 11 min walk - 0.6 miles
  • Chestertown Dog Park - 17 min walk - 0.9 miles
  • Historical Society of Kent County Maryland - 3 min drive - 1.7 miles
  • Chestertown Historic District - 3 min drive - 1.7 miles

Getting around

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

Restaurants

  • ‪Royal Farms - ‬2 min drive
  • ‪McDonald's - ‬9 min walk
  • ‪Dunkin - ‬3 min walk
  • ‪Procolino's - ‬9 min walk
  • ‪Arby's - ‬5 min walk

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

Lobby
Comfort Inn & Suites Chestertown
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
4.3 out of 5, Excellent, 863 reviews
$98 nightly
The price is $109
Jan 25 - Jan 26
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
  • Limited onsite self parking
  • 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 Jan 3, 2026, prices found for a 1-night stay for 2 adults at Red Roof Inn & Suites Chestertown on Jan 10, 2026 start from $72.0, 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. 123 out of 425 reviews
Rating 8 - Good. 129 out of 425 reviews
Rating 6 - Okay. 83 out of 425 reviews
Rating 4 - Poor. 54 out of 425 reviews
Rating 2 - Terrible. 36 out of 425 reviews

7.4/10

Cleanliness

7.8/10

Staff & service

5.6/10

Amenities

6.8/10

Property conditions & facilities

6.8/10

Eco-friendliness

Reviews

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

10/10 Excellent

lisa

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Time to upgrade the furniture in the rooms. The staff is doing a GREAT JOB cleaning and providing excellent service.
Stayed 1 night in Aug 2025

6/10 Okay

Robert

Liked: Staff & service
Well it's not a five-star hotel but then again they don't claim to be a five-star hotel. All in all things were pretty good it is outdated and although I searched everything with my flashlight for bed bugs and did not find a dead one or a live one. Everything functioned like it's supposed to but some fresh paint and maybe shampooing some carpets would be a large improvement towards the musty smell and overall cleanliness. I'm sure you could find a cleaner more updated hotel somewhere but for the price I got a good night sleep for the one night I was passing through. Especially on Labor Day weekend.
Stayed 1 night in Aug 2025

10/10 Excellent

Linda

Business traveler
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very convenient for the purpose i was there for.
Stayed 2 nights in Aug 2025

10/10 Excellent

Cynthia

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We had a great stay with our two Pups.. The room was very nice and comfortable and very clean.
Stayed 2 nights in Aug 2025

8/10 Good

Jeffrey

Stayed 3 nights in Aug 2025

4/10 Poor

John

Knowing that I chose a lower cost room I understand the expectations should not be a Hilton. The grounds were overgrown and when we were leaving there was no one at the front desk. There were holes in the carpet, wall Paper coming off the walls and our bed had three “throw” pillows, but again I understand at least a place to sleep.
Stayed 1 night in Aug 2025

6/10 Okay

Everett

Air conditioner was extremely noisy. Finally had to turn it off to get to sleep. Then the room got hot. Wi-fi password changed at midnight, so had to go to front desk in the morning to get the new password. Window curtain was hanging loose at top. Didn't affect night time lighting, but looked bad. Property not really in very good shape.
Stayed 1 night in Aug 2025

10/10 Excellent

Maria

Liked: Cleanliness, staff & service, property conditions & facilities
Great service
Stayed 3 nights in Jul 2025

8/10 Good

Gale

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Did not like lack of vending services
Stayed 1 night in Jul 2025

2/10 Terrible

Linley

Disliked: Cleanliness, property conditions & facilities
Bad experience
Stayed 1 night in Jul 2025

6/10 Okay

Verified traveler

Business traveler
Liked: Room comfort
Front desk and cleaning lady were nice and helpful. Very accommodating since I had to switch rooms twice. Once for tv not working and second due to overpowering air freshener smell in the room. Rooms are outdated. TV’s definitely need updating. Disappointed that their pool has been out of service. Bedding and sheets were clean and comfortable.
Stayed 4 nights in Jul 2025

8/10 Good

Robert

Liked: Cleanliness, staff & service
Friendly/helpful staff, clean facilities. Room A/C was leaking condensation into the carpet, soaking it a good 4-5 inches away from the unit. Shower was slow to transition from bath faucet to shower head and never fully switched over (water pressure from the head was adequate, though.) You can tell the place is aging but its still cozy and very serviceable. Pretty decent value for the price. I was satisfied.
Stayed 1 night in Jul 2025

10/10 Excellent

Marie Paz

Business traveler
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

SweetyPie The Explorer from Florida

Our check-in quicl Staff was quick. The rooms have a very spacious area it was clean and the beds were comfortable just for a night to crash.
Stayed 1 night in Jul 2025

6/10 Okay

Eric

Traveled with family
Disliked: Amenities
Good location.
Stayed 1 night in Jul 2025

4/10 Poor

Peter

Traveled with partner
Liked: Staff & service
Disliked: Amenities
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.
Stayed 1 night in Jul 2025