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Red Roof Inn & Suites Chestertown

2.0 star property
Guests can warm up by the lobby fireplace, explore Chestertown's hidden downtown gems, and experience attentive service from the helpful staff.

Choose dates to view prices

Red Roof Inn & Suites in Chestertown offers a welcoming base with practical amenities like laundry facilities, WiFi, lobby coffee, and extended parking. Guests consistently felt supported by the staff during their stays.

Reviews

7.2 out of 10
Good

Popular amenities

  • Pet-friendly
  • Parking included
  • Free Wi-Fi
  • Air-conditioning
  • Laundry room
  • Housekeeping
The current price is NZ$136
includes taxes & fees
5 Apr - 6 Apr

Room options

Available filters for rooms
Showing 4 of 4 rooms

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

Desk, laptop workspace, blackout curtains, iron/ironing board

Superior Room, 1 King Bed, Accessible, Non Smoking

8.6 out of 10
Excellent
(9 reviews)

Highlights

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

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

Desk, laptop workspace, blackout curtains, iron/ironing board

Superior Room, 1 King Bed, Accessible, Non Smoking

7.2 out of 10
Good
(12 reviews)

Highlights

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

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

Desk, laptop workspace, blackout curtains, iron/ironing board

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

7.0 out of 10
Good
(18 reviews)

Highlights

Air conditioning
Heating
Free cots/infant beds
Mini-fridge
Flat-screen TV
Separate bedroom
Blackout curtains
Hairdryer
  • 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

Suite, Multiple Beds, Non Smoking

8.4 out of 10
Very good
(17 reviews)

Highlights

Air conditioning
Heating
Free cots/infant beds
Mini-fridge
Flat-screen TV
Separate bedroom
Blackout curtains
Hairdryer
  • 42 sq m
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed
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About the area

Located in Chestertown, Red Roof Inn & Suites Chestertown is in the city centre. Rolphs Wharf Marina and Cassinelli Winery and Vineyards are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Rolling Road Park and Chestertown Historic District. Larrabee Arts Center and Garfield Center for the Arts at the Prince Theater are also worth visiting. Visit our Chestertown travel guide
Map
160 Scheeler Rd, Chestertown, MD, 21620

What's nearby

  • Eastern Shore Maryland, USA is between the Chesapeake bay and Delaware Bay. There are so many farms and fresh produce in this area just 20 minutes from the surrounding water ways. There are also small venues to eat and all have great crabs and crab bisque.
    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

  • Baltimore Washington International Airport (BWI)
    80 min drive

Restaurants

  • Milano's Pizzeria
    5 min drive
  • Royal Farms
    5 min drive
  • Dunkin
    3 min walk
  • McDonald's
    9 min walk
  • Royal Farms
    2 min drive

About this property

Red Roof Inn & Suites Chestertown

Hotel in the city centre
Red Roof Inn & Suites Chestertown provides amenities, such as laundry facilities and a fireplace in reception. Guests can connect to free in-room WiFi.
Additional perks include:
  • Free self-parking
  • Coffee/tea in reception, a 24-hour front desk and a vending machine
  • A TV in reception, free newspapers and a lift
  • Guest reviews speak highly of the helpful staff
Room features
All 53 rooms have comforts such as laptop-friendly workspaces and air conditioning, in addition to thoughtful touches such as free WiFi and desk chairs.
More amenities include:
  • Bathrooms with free toiletries and hairdryers
  • 43-inch flat-screen TVs with premium channels
  • Mini fridges, microwaves and free infant beds

Similar properties

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Comfort Inn & Suites Chestertown
  • Pool
  • Breakfast included
  • Pet-friendly
  • Parking included
8.6 out of 10, Excellent, 882 reviews
The price is NZ$190
includes taxes & fees
15 Mar - 16 Mar
Comfort Inn & Suites Chestertown
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Property amenities

Internet

  • Available in all rooms: Free WiFi
  • Available in some public areas: Free WiFi

Parking and transport

  • Free uncovered self parking on site
  • Free RV/bus/lorry parking on site
  • Limited on-site self parking
  • Wheelchair-accessible parking available

Food and drink

  • Coffee and tea in common areas

Things to do

  • TV in common areas

Family friendly

  • In-room cot
  • 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.
  • Lever door handles
  • Lift
  • Well-lit path to entrance
  • Wheelchair accessible (may have limitations)
  • Wheelchair-accessible parking
  • Wheelchair-accessible path of travel
  • Wheelchair-accessible path to lift
  • 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 cot

Bathroom

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

Entertainment

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

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

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 are allowed for an extra charge of USD 15 per pet, per night (maximum USD 105 per stay)
Service animals are welcome, and are exempt from fees
Welcoming dogs and cats only
2 total (up to 36 kg per pet)
Pets cannot be left unattended
Restrictions apply; for more information contact the property on the number on the booking confirmation

Children and extra beds

Children are welcome
3 children, up to the age of 17 years, can stay for free if using existing beds when occupying the parent or guardian's room
Rollaway/extra beds are not available.
Free cots are available on request at the property

Payment types

Important information

Fees

You'll be asked to pay the following charges at the property. Fees may include applicable taxes:

  • Deposit: USD 100.00 per accommodation, per stay

We have included all charges provided to us by the property.

Optional extras

  • Pet fee: USD 15 per pet, per night (maximum USD105 per stay)
  • Service animals are exempt from fees

The above list may not be comprehensive. Fees and deposits may 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
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

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

Is Red Roof Inn & Suites Chestertown pet-friendly?

Yes, Red Roof Inn & Suites Chestertown allows cats and dogs (limit 2 total) with a maximum weight of up to 36 kg per pet. There's a fee 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.

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

As of 7 Mar 2026, prices found for a 1-night stay for 2 adults at Red Roof Inn & Suites Chestertown on 5 Apr 2026 start from NZ$136, including 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.

How much is parking at Red Roof Inn & Suites Chestertown?

Self-parking is free at this property.

What time is check-in at Red Roof Inn & Suites Chestertown?

Check-in start time: 3 PM; check-in end time: anytime.

What time is check-out at Red Roof Inn & Suites Chestertown?

Checkout is at 11 AM.

Where is Red Roof Inn & Suites Chestertown located?

Located in the heart of Chestertown, this hotel is within 1 mile (2 km) of Washington College, Rolling Road Park and Larrabee Arts Center. Chestertown Dog Park and Historical Society of Kent County Maryland are also within 2 miles (3 km).

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Reviews

Red Roof Inn & Suites Chestertown Reviews

7.2

Good

7.4

Cleanliness

8.6

Location

7.8

Staff & service

6.6

Property conditions & facilities
Rating 10 - Excellent. 125 out of 429 reviews
Rating 8 - Good. 129 out of 429 reviews
Rating 6 - Okay. 83 out of 429 reviews
Rating 4 - Poor. 55 out of 429 reviews
Rating 2 - Terrible. 37 out of 429 reviews

Reviews

10/10 Excellent

Linette

Liked: Cleanliness, property conditions & facilities
Arrived earlier than expected and the staff was very accommodating and friendly which made for an excellent stay from start to finish.
Stayed 1 night in Nov 2025

8/10 Good

Robert

Liked: Cleanliness, amenities, property conditions & facilities
Clean and friendly staff. Good location.
Stayed 1 night in Oct 2025

8/10 Good

Dr. Nicholas and Mrs. Karen

Liked: Cleanliness, property conditions & facilities
Professional staff, warm greetings clean room
Stayed 4 nights in Nov 2025

10/10 Excellent

lisa

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

10/10 Excellent

Kellie

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

10/10 Excellent

Federico

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Well received by front desk attendant. Clean room!
Stayed 1 night in Oct 2025

10/10 Excellent

Vicente

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very nice location and area
Stayed 1 night in May 2025

10/10 Excellent

Gary

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Easy to get to, food all around!
Stayed 1 night in Mar 2025

10/10 Excellent

lisa

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

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

8/10 Good

Matthew

Liked: Cleanliness, staff & service
Staff was very friendly
Stayed 1 night in Oct 2024

10/10 Excellent

DAMEION

Liked: Cleanliness, staff & service, property conditions & facilities
Have stayed here several times. Nice staff and clean rooms. Can walk for food
Stayed 1 night in Jan 2025

10/10 Excellent

April

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

Nice place to stay

Staff were very kind. Easy parking and comfortable rooms.
Stayed 2 nights in Aug 2024

4/10 Poor

Peter

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

10/10 Excellent

April

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

Great Place

Amazing stay. Wonderful hotel, comfortable beds, very clean. Super nice staff.
Stayed 2 nights in Aug 2023

8/10 Good

Shannon

Liked: Cleanliness, staff & service, property conditions & facilities
Disliked: Amenities
We have stayed here many times before and I was able to book a one night stay for our quick trip this time. Very comfortable and relaxing, rooms are nice
Stayed 1 night in May 2024

10/10 Excellent

Bonney

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excellent value for the price. Accessible location, very quiet, clean, everything we needed was in our rooms.
Stayed 2 nights in Oct 2023

8/10 Good

Rebecca

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was clean
Stayed 5 nights in May 2025

8/10 Good

Craig

Liked: Cleanliness, staff & service
A little rough around the edges in some ways, but the rooms were large, quiet, and clean.
Stayed 1 night in Oct 2024

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

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

6/10 Okay

James

Liked: Cleanliness, staff & service
Reception staff was friendly and helpful.
Stayed 3 nights in Sep 2023

10/10 Excellent

Terry dian

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

Good stay

Staff was very pleasant and helpful
Stayed 1 night in Oct 2023

10/10 Excellent

alaiyah

Liked: Cleanliness, staff & service, property conditions & facilities
nice hotel. helpful staff. stores and dining are walkable distances.
Stayed 4 nights in May 2024

6/10 Okay

Verified traveller

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