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Red Roof Inn & Suites Chestertown

2.0 star property
Chestertown hotel in historical district

Choose dates to view prices

Photo gallery for Red Roof Inn & Suites Chestertown

Suite, Multiple Beds, Non Smoking | 1 bedroom, desk, laptop workspace, blackout drapes
1 bedroom, desk, laptop workspace, blackout drapes
Lobby lounge
Exterior
Lobby lounge
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.

Reviews

7.2 out of 10
Good

Popular amenities

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

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
The current price is $76
$85 total
includes taxes & fees
Sep 14 - Sep 15

Room options

Check availability for these dates

Tonight

Sep 6 - Sep 7
Check availability for tonight Sep 6 - Sep 7

Tomorrow

Sep 7 - Sep 8
Check availability for tomorrow Sep 7 - Sep 8
Available filters for rooms
Showing 4 of 4 rooms

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

1 bedroom, desk, laptop workspace, blackout drapes

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

7.0 out of 10
Good
(18 reviews)

Highlights

Air conditioning
Heating
Free cribs/infant beds
Mini-fridge
Flat-screen TV
Separate bedroom
Blackout drapes/curtains
Private bathroom
  • 39 sq m
  • 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 | 1 bedroom, desk, laptop workspace, blackout drapes

Suite, Multiple Beds, Non Smoking

8.4 out of 10
Very good
(15 reviews)

Highlights

Air conditioning
Heating
Free cribs/infant beds
Mini-fridge
Flat-screen TV
Separate bedroom
Blackout drapes/curtains
Private bathroom
  • 42 sq m
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed

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

1 bedroom, desk, laptop workspace, blackout drapes

Superior Room, 1 King Bed, Accessible, Non Smoking

8.4 out of 10
Very good
(8 reviews)

Highlights

Air conditioning
Heating
Free cribs/infant beds
Mini-fridge
Flat-screen TV
Blackout drapes/curtains
Separate bedroom
Private bathroom
  • 39 sq m
  • Sleeps 2
  • 1 King Bed

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

1 bedroom, desk, laptop workspace, blackout drapes

Superior Room, 1 King Bed, Accessible, Non Smoking

7.6 out of 10
Good
(11 reviews)

Highlights

Air conditioning
Heating
Free cribs/infant beds
Mini-fridge
Flat-screen TV
Blackout drapes/curtains
Separate bedroom
Hair dryer
  • 39 sq m
  • Sleeps 2
  • 1 King Bed

Similar properties

Lobby

Comfort Inn & Suites Chestertown

  • Pool
  • Pet friendly
  • Free parking
  • Free WiFi
8.6 out of 10, Excellent, 810 reviews
The price is $110
$122 total
includes taxes & fees
Sep 14 - Sep 15
Comfort Inn & Suites Chestertown
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About the neighborhood

Map
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
  • River Arts Chestertown - 3 min drive - 3.1 km
  • Rolphs Wharf Marina - 15 min drive - 11.8 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

  • ‪Milano's Pizzeria - ‬5 min drive
  • ‪Dunkin - ‬3 min walk
  • ‪Procolino's - ‬9 min walk
  • ‪Subway - ‬2 min drive
  • ‪Evergrain Bread Company - ‬3 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

DONE

Hotel size

    • 53 rooms
    • Arranged over 3 floors
DONE

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
DONE

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.
DONE

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
DONE

Children

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

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
DONE

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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Red Roof Inn & Suites Chestertown Reviews

Reviews

7.2

Good

7.6/10

Cleanliness

7.8/10

Staff & service

5.6/10

Amenities

6.8/10

Property conditions & facilities

6.8/10

Eco-friendliness

Popular mentions

Room
Service staff
Bathroom
Breakfast
Couch
Shower
Bed
Lobby
Desk
Value

Reviews

8/10 Very good

Was a decent place to stay for the price.
darrell, 1-night trip

10/10 Exceptional

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

8/10 Very good

Clean, spacious, affordable accommodations.
James, 4-night trip

8/10 Very good

Good hotel and good value.
charlene, 1-night trip

10/10 Exceptional

Very accommodating and polite staff
2-night trip

10/10 Exceptional

Easy to get to, food all around!
Gary, 1-night trip

8/10 Very good

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

10/10 Exceptional

Affordable
CAROLE, 1-night trip

6/10 Good

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

4/10 Fair

No water pressure. AC not working. Hair dryer not working. Comfortable bed
Larry, 1-night trip

6/10 Good

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.
Everett, 1-night trip

8/10 Very good

Relaxing.
Carl, 2-night trip

10/10 Exceptional

I stayed here one night and got a stripper pregnant. 10/10 will book again.
Connor, 1-night trip

8/10 Very good

It was clean
Rebecca, 5-night trip

10/10 Exceptional

I loved the decor of my room. The king size bed was cozy.
Crystal, 1-night trip

4/10 Fair

Convenient to Chestertown. No breakfast. No regular coffee in room. No creamer or sugar. Couch and floor dirty
debra, 1-night trip

4/10 Fair

Carpet begs to be put out of its misery. Really gross in lobby. And no breakfast at all? Cheap!
Michael, 3-night trip

6/10 Good

Old property carpets and couch stained
debra, 1-night trip

6/10 Good

Our Red Roof Inn, July 11-12, 2025

If the price wasn't what it was, we'd have booked the Comfort Inn next door. Our impression is that this Red Roof Inn provides worker housing for local businesses. That's not a plus when on a vacation. Which is not meant to be a slur against people working to make a living. My wife was offput by the state of the rugs in the hall; No coffee or breakfast services since Covid, according to the desk person. And the toilet in our room rocked. Which was unsettling. On the plus side the room was in reasonably decent shape. The bed and especially the pillows were very good and clean. We come to this area once a year for an event and will most likely stay there again. So it's a mixed bag, but mostly to the positive side.
2-night trip

10/10 Exceptional

Have stayed here several times. Nice staff and clean rooms. Can walk for food
DAMEION, 1-night trip

2/10 Poor

First room- Really bad room. AC broken. Next room completely smokey. Didn't have any ok rooms.
Lee, 1-night trip

6/10 Good

The property was dated and dirty
jeffrey, 3-night trip

6/10 Good

The property is out of date with worn old furniture. While it was clean it was old.
Anthony, 1-night trip

6/10 Good

not worth the money
Brenda, 1-night trip

10/10 Exceptional

good hotel

Great Place to stay
2-night trip