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Red Roof Inn & Suites Chestertown

2.0 star property
Hotel in Chestertown with free parking

Choose dates to view prices

Photo gallery for Red Roof Inn & Suites Chestertown

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

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, Garfield Center for the Arts at the Prince Theater
    ‪3 min drive‬
  • 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

Red Roof Inn & Suites Chestertown places you within a short walk of Washington College and within a mile (2 km) of Rolling Road Park. Each of the 53 rooms at this hotel includes a microwave, a coffee maker, and a flat-screen TV.

What's nearby

  • Washington College - 8 min walk - 0.4 miles
  • Rolling Road Park - 11 min walk - 0.6 miles
  • Garfield Center for the Arts at the Prince Theater - 3 min drive - 1.7 miles
  • Chestertown Historic District - 3 min drive - 1.7 miles
  • Historical Society of Kent County Maryland - 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 - ‬2 min drive
  • ‪Dunkin - ‬3 min walk
  • ‪Royal Farms - ‬5 min drive
  • ‪McDonald's - ‬9 min walk

About this property

Red Roof Inn & Suites Chestertown

Hotel in Chestertown with free parking
Red Roof Inn & Suites Chestertown features free WiFi in public areas, coffee in a common area, and free newspapers. You can put free parking to good use if you drive. The 24-hour front desk has staff always at the ready. Additional amenities include laundry facilities, a TV in a common area, and a vending machine.
43-inch flat-screen TVs come with cable channels and pay movies, and guests can stay connected with free WiFi. Bathrooms have hair dryers and free toiletries. Other standard amenities include microwaves, coffee makers, and free long-distance calls. Change of towels is available on request.

Similar properties

Free daily full breakfast
Comfort Inn & Suites Chestertown
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
8.6 out of 10, Excellent, 870 reviews
$101 nightly
The price is $112
Mar 1 - Mar 2
Total with taxes and fees
Comfort Inn & Suites Chestertown

Property amenities

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

Family friendly

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

Conveniences

  • 24-hour front desk
  • Free newspapers in lobby
  • Laundry facilities
  • Vending machine

Guest services

  • Change of bedsheets (on request)
  • Change of towels on request
  • Housekeeping (daily)

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

More

  • 1 building
  • 3 floors
  • Built in 1996
  • Designated smoking areas
  • Fireplace in lobby

Room amenities

Bedroom

  • Bedsheets provided
  • Blackout drapes
  • Free crib

Bathroom

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

Entertainment

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

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

  • This property welcomes pets for USD 15 per pet, per night (maximum USD 105 per stay)
  • Dogs and cats only
  • 2 total (80 lbs is the maximum weight per pet)
  • Pets may not be left unsupervised
  • Restrictions apply
  • For more information, guests can reach out to the property at the number on the booking confirmation
  • Service animals exempt from fees

Children and extra beds

  • Up to 3 kids 17 years old and younger stay free when using existing bedding
  • Free cribs/infant beds are available

Property payment types

Important information

Fees

You'll be asked to pay these charges at the property:

  • Deposit: USD 100.00 per accommodation, per stay

These are all of the charges provided to us by the property.

Optional extras

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

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

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

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
  • Check-in: 3 PM—-anytime
  • Check-out: 11 AM
  • Minimum check-in age: 21
The front desk is open 24 hours a day. Driving? This property offers free self parking, along with free RV, bus, and truck parking.

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • This property accepts credit cards. Cash is not accepted. 

Additional information about polices, regulations, and more:

  • No rollaway or extra beds are available.
  • Noise-free rooms can't be guaranteed.
  • 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

What's there to do near Red Roof Inn & Suites Chestertown?

This hotel is located in Chestertown within a short 16-minute walk of Rolling Road Park. You'll also find Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater within a short drive.

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

As of Feb 2, 2026, prices found for a 1-night stay for 2 adults at Red Roof Inn & Suites Chestertown on Feb 8, 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.

Will I be able to park at Red Roof Inn & Suites Chestertown?

Yes, uncovered self parking is offered for free at the hotel. Accessible parking and free RV/bus/truck parking are also available for guests.

Does Red Roof Inn & Suites Chestertown have a casino?

No, Red Roof Inn & Suites Chestertown doesn't have a casino.

Is there an indoor pool at Red Roof Inn & Suites Chestertown?

No, there is no indoor pool at this hotel.

Does Red Roof Inn & Suites Chestertown have a hot tub?

No, there isn't a spa tub at this hotel.

Does Red Roof Inn & Suites Chestertown feature a restaurant that includes a breakfast menu?

No, Red Roof Inn & Suites Chestertown doesn't have a restaurant that serves breakfast.

Does Red Roof Inn & Suites Chestertown allow pets to stay for free?

Although they can't stay for free, cats and dogs are welcome at Red Roof Inn & Suites Chestertown for a fee of USD 15 per pet, per night.

Does Red Roof Inn & Suites Chestertown have connecting rooms?

No, this hotel doesn't feature connecting guestrooms.

What is the closest airport to Red Roof Inn & Suites Chestertown?

The closest major airport to Red Roof Inn & Suites Chestertown is Baltimore, MD (MTN-Martin State), which is about 20.1 mi away. Another top airport is Easton, MD (ESN-Easton - Newnam), which is around 28.7 mi away.

Can I book a room with a balcony at Red Roof Inn & Suites Chestertown?

No, you won't find guestrooms with balconies at Red Roof Inn & Suites 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

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

10/10 Excellent

Federico, Plymouth

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Well received by front desk attendant. Clean room!
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

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

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