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Red Roof Inn & Suites Chestertown - Image 1
Red Roof Inn & Suites Chestertown - Room
Red Roof Inn & Suites Chestertown - Room
Red Roof Inn & Suites Chestertown - Lobby lounge
Red Roof Inn & Suites Chestertown - Lobby lounge

Red Roof Inn & Suites Chestertown


Amenities

  • Free Wi-Fi

  • Elevator / Lift

  • Designated Smoking Area

  • Vending Machines

  • 24-Hour Front Desk

  • Coffee/Tea in Common Areas

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Property description

Make use of convenient amenities such as complimentary wireless internet access, a fireplace in the lobby, and a vending machine.
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From

$72
/ night

Guest reviews

What guests think

AI-generated summary based on recent guest reviews























10

Dom

IAN-logo

Apr 26, 2026

·

Stayed 1 night

Clean lady was nice help me out
Clean lady was nice help me out

10

Lisa

IAN-logo

Apr 24, 2026

·

Stayed 1 night

Don't sleep on Chestertown Red. It has come from 3 to 8 1/2. The own needs to step up and fix the pool and start giving breakfast. But for now I will be back. Great Staff.
Don't sleep on Chestertown Red. It has come from 3 to 8 1/2. The own needs to step up and fix the pool and start giving breakfast. But for now I will be back. Great Staff.

10

Lisa

IAN-logo

Apr 7, 2026

·

Stayed 2 nights

Was very clean and fresh.
Was very clean and fresh.

4

Kevin

IAN-logo

Mar 23, 2026

·

Stayed 1 night

The property is disheveled and dirty. Front desk attendant gave us our room and then tried to break into it saying that it was already booked to someone else and we shouldn't have been in there. My son tried to explain that it was his room, and she tried to use a screwdriver to pop the security latch. Gross and poor facility.
The property is disheveled and dirty. Front desk attendant gave us our room and then tried to break into it saying that it was already booked to someone else and we shouldn't have been in there. My son tried to explain that it was his room, and she tried to use a screwdriver to pop the security latch. Gross and poor facility.

10

Tim

IAN-logo

Mar 23, 2026

·

Stayed 2 nights

Stay was great. Booked 3 rooms for a family event. Check in was great and the staff was awesome. My room out of the 3 had an issue with the AC/heat. I explained the issue the next morning and when realizing they couldn’t fix the issue they were able to put us in another room. Very kind and professional.
Stay was great. Booked 3 rooms for a family event. Check in was great and the staff was awesome. My room out of the 3 had an issue with the AC/heat. I explained the issue the next morning and when realizing they couldn’t fix the issue they were able to put us in another room. Very kind and professional.

160 Scheeler Rd, Chestertown, Maryland, United States of America

Location

A stay at Red Roof Inn & Suites Chestertown places you in the heart of Chestertown, within a 5-minute drive of Washington College and Larrabee Arts Center. This hotel is 0.8 mi (1.3 km) from Rolling Road Park and 0.9 mi (1.4 km) from Chestertown Dog Park.

Washington College(0.5 miles)

Rolling Road Park(0.9 miles)

Larrabee Arts Center(1 miles)

Chestertown Dog Park(1 miles)

Historical Society of Kent County Maryland(1.6 miles)

Wilmer Park(1.7 miles)

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Property Policies

Check-in instructions

Everything you need to know for a smooth check-in.

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Check-in

Check-out

From 15:00 to 23:59

Before 11:00


Security deposit

You'll be required to pay the fully refundable deposit for this property.

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Good to know

Additional policies and info about this property.

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Optional extras

Additional paid services you can request.

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FAQs

Free self-parking is available on-site, including designated parking for RVs, buses, and trucks. The parking is uncovered.


Pets are allowed, with no charge for one pet. A fee of $15 per additional pet per night applies, with a maximum fee of $105 per stay. Service animals are exempt from fees.


Check-in is at 3:00 PM and check-out is at 11:00 AM. Early or late check-in/check-out may be available upon request, but additional charges may apply.

The hotel offers several accessibility features including a wheelchair-accessible registration desk, limited wheelchair-accessible rooms, elevators, and well-lit paths to the entrance.


The hotel is located in the heart of Chestertown, within a 5-minute drive of Washington College and Larrabee Arts Center. It is 0.8 miles from Rolling Road Park and 0.9 miles from Chestertown Dog Park.


Up to 3 children aged 17 years and younger can stay free when occupying the parent or guardian's room, using existing bedding.


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