Red Roof Inn & Suites Chestertown

City-center hotel in Chestertown

Choose dates to view prices

Where to?

Dates

November 2025

19

December 2025

Suite, Multiple Beds, Non Smoking | 1 bedroom, desk, laptop workspace, blackout drapes

1 bedroom, desk, laptop workspace, blackout drapes

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.

Good

Popular amenities

Laundry facilities
Pet friendly
Air conditioning
Free WiFi
24/7 front desk
Free parking

Main amenities (9)

Daily housekeeping
24-hour front desk
Coffee/tea in a common area
Air conditioning
Lobby fireplace
Vending machine
Self-serve laundry
Free newspapers in the lobby
TV in a common area

For families (6)

Children stay free
Free cribs/infant beds
Microwave
Private bathroom
Premium TV channels
Daily housekeeping

$80 total

includes taxes & fees

Nov 30 - Dec 1

Room options

Check availability for these dates

Tonight

Nov 19 - Nov 20

Tomorrow

Nov 20 - Nov 21

All rooms

1 bed

2 beds

3+ beds

Showing 4 of 4 rooms

Superior Room, 1 King Bed, Accessible, Non Smoking

Very good

Highlights

Air conditioning

Heating

Free cribs/infant beds

Mini-fridge

Flat-screen TV

Separate bedroom

Blackout drapes/curtains

Shower/tub combination

39 sq m
Sleeps 2
1 King Bed

Superior Room, 1 King Bed, Accessible, Non Smoking

Good

Highlights

Air conditioning

Heating

Free cribs/infant beds

Mini-fridge

Flat-screen TV

Separate bedroom

Blackout drapes/curtains

Private bathroom

39 sq m
Sleeps 2
1 King Bed

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

Good

Highlights

Air conditioning

Heating

Free cribs/infant beds

Mini-fridge

Flat-screen TV

Separate bedroom

Blackout drapes/curtains

Shower/tub combination

39 sq m
1 bedroom
Sleeps 4
1 King Bed and 1 Double Sofa Bed

Suite, Multiple Beds, Non Smoking

Very good

Highlights

Air conditioning

Heating

Free cribs/infant beds

Mini-fridge

Flat-screen TV

Separate bedroom

Blackout drapes/curtains

Shower/tub combination

42 sq m
1 bedroom
Sleeps 6
2 Queen Beds and 1 Double Sofa Bed

Similar properties

Pool
Pet friendly
Free parking
Free WiFi

$113 total

includes taxes & fees

Nov 23 - Nov 24

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About the neighborhood

160 Scheeler Rd, Chestertown, MD, 21620

What's nearby

Washington College - 8 min walk - 0.7 km
Chestertown Dog Park - 17 min walk - 1.5 km
Historical Society of Kent County Maryland - 3 min drive - 2.8 km
Chestertown Historic District - 3 min drive - 2.8 km
River Arts Chestertown - 3 min drive - 2.8 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

‪Royal Farms - ‬2 min drive
‪McDonald's - ‬9 min walk
‪Dunkin - ‬3 min walk
‪Procolino's - ‬9 min walk
‪Subway - ‬2 min drive

About this property

Red Roof Inn & Suites Chestertown

Enjoy your visit to Chestertown with a stay at Red Roof Inn & Suites Chestertown. You'll have free perks like WiFi and self parking. Fellow travelers love the helpful staff.

At a glance

Hotel size

- 53 rooms
- Arranged over 3 floors

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

Special check-in instructions

- Front desk staff will greet guests on arrival at the property
- This property allows guests 18 or over to check in with valid military ID.

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

Children

- Up to 3 children (17 years old and younger) stay free when occupying the parent or guardian's room, using existing bedding

Pets

- Pets allowed (dogs and cats only, 2 total, up to 80 lbs per pet)*
- Service animals welcome
- Restrictions apply*
- Pets must be supervised

Internet

- Free WiFi in public areas
- Free WiFi in rooms

Parking

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

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 16 minutes' walk from Rolling Road Park.

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Red Roof Inn & Suites Chestertown Reviews

7.2

Good

7.4

Cleanliness

8.6

Location

7.8

Staff & service

6.8

Eco-friendliness

6.6

Property conditions & facilities

Popular mentions

Room

Service staff

Bathroom

Breakfast

Couch

Shower

Bed

Lobby

Furniture

Coffee

10/10 Exceptional

Oct 6, 2025

Wish they had the pool open. The staff is great here and very helpful.

lisa, 2-night trip

10/10 Exceptional

Sep 27, 2025

Room temperature was good. Room was also very spacious and clean.

Kellie, 1-night trip

6/10 Good

Jul 21, 2025

Good location.

Eric, 1-night trip

10/10 Exceptional

Jul 3, 2025

Had a good time and enjoyed the quietness at the hotel.

Chenlin, 1-night trip

8/10 Very good

May 29, 2025

Was a decent place to stay for the price.

darrell, 1-night trip

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, 3-night trip

8/10 Very good

May 9, 2025

Good hotel and good value.

charlene, 1-night trip

10/10 Exceptional

Aug 1, 2025

Great service

Maria, 3-night trip

8/10 Very good

Jun 3, 2025

Clean, spacious, affordable accommodations.

James, 4-night trip

10/10 Exceptional

May 19, 2025

Very nice location and area

Vicente, 1-night trip

10/10 Exceptional

Jul 21, 2025

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.

Marie Paz, 1-night trip

10/10 Exceptional

Apr 20, 2025

Easy to get to, food all around!

Gary, 1-night trip

10/10 Exceptional

May 20, 2025

Very accommodating and polite staff

2-night trip

10/10 Exceptional

Jun 24, 2025

Great

Michael, 1-night trip

4/10 Fair

Sep 6, 2025

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.

1-night trip

8/10 Very good

May 20, 2025

Have stayed there a few times. Nothing spectacular but very adequate. Not many people there aby of the times I have stayed there

keith, 1-night trip

8/10 Very good

Jul 9, 2025

Pretty decent room size. AC didn't work very well, but we survived. Good experience overall.

Michael, 1-night trip

10/10 Exceptional

May 21, 2025

Affordable

CAROLE, 1-night trip

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, 1-night trip

4/10 Fair

Aug 12, 2025

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.

John, 1-night trip

8/10 Very good

Jul 28, 2025

Did not like lack of vending services

Gale, 1-night trip

8/10 Very good

Jul 26, 2025

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.

Robert, 1-night trip

6/10 Good

Jul 27, 2025

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.

4-night trip