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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 WiFi
  • Air conditioning
  • Laundry
  • Housekeeping
The current price is ₩107,767
₩119,621 total
includes taxes & fees
May 27 - May 28
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About this property

Red Roof Inn & Suites Chestertown

  • Hotel in the city center
  • Red Roof Inn & Suites Chestertown provides amenities like laundry facilities and a fireplace in the lobby. Guests can connect to free in-room WiFi.
  • Additional perks include:
    • Free self parking
    • A vending machine, coffee/tea in the lobby, and a 24-hour front desk
    • Free newspapers, a TV in the lobby, and an elevator
    • Guest reviews give top marks for the helpful staff
  • Room features
  • All 53 rooms feature comforts such as laptop-friendly workspaces and air conditioning, in addition to thoughtful touches like free WiFi and desk chairs.
  • Extra amenities include:
    • Bathrooms with free toiletries and hair dryers
    • 43-inch flat-screen TVs with premium channels
    • Mini fridges, microwaves, and free infant beds

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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

Pets 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 80 lbs per pet)

Pets cannot be left unattended

Restrictions apply; for more information contact the property at 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 cribs are available on request at the property

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 USD 105 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)

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 80 lbs 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 May 21, 2026, prices found for a 1-night stay for 2 adults at Red Roof Inn & Suites Chestertown on May 27, 2026 start from ₩107,767, 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.

How much is parking?

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?

Check-out is at 11 AM.

Where is Red Roof Inn & Suites Chestertown located?

Located in the heart of Chestertown, this hotel is within 1 mi (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 mi (3 km).

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Reviews

Reviews

7.2

Good

7.4

Cleanliness

8.6

Location

7.8

Staff & service

6.6

Property conditions & facilities
Rating 10 - Excellent. 130 out of 441 reviews
Rating 8 - Good. 130 out of 441 reviews
Rating 6 - Okay. 86 out of 441 reviews
Rating 4 - Poor. 57 out of 441 reviews
Rating 2 - Terrible. 38 out of 441 reviews

Reviews

Verified

10/10 Excellent

Thomas

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
A significant improvement compared to my previous stays in terms of cleanliness and upkeep. The receptionists were also helpful.
Stayed 2 nights in Apr 2026
Verified

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
Verified

6/10 Okay

Michael

Liked: Property conditions & facilities
Disliked: Amenities
Its OK considering the inexpensive cost per night. The room was clean with the exceprion of a dead wasp under the bathroom vanity. Lobby staff was professional when we checked in, although not a particularly happy greeting...note: a smile and a "Hello" instead of just a straight faced "Checking in?" greeting goes a long way towards good customer "first impressions". Room amenities are minimal but adequate for a night. Overall, its OK.
Stayed 1 night in Apr 2026
Verified

8/10 Good

Robert

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

8/10 Good

David

I had very low expectations based on some of the reviews. But I was not exposed to the things I feared most from the reviews...dead bugs, unclean room, rude staff, bad smells...perhaps I was lucky, perhaps they've improved based on those reviews. My room was clean, everything worked inside the room. That the towels were skimpy is my biggest complaint about the room. The walls were "thin" but there was only minimal and occasional noise from my neighbors. The property itself needs a good spring cleaning, especially the hallway carpets, the broken beverage vending machine should be fixed, the pool should be usable, and this property still advertises free breakfast...nope. But I was overall satisfied.
Stayed 3 nights in Apr 2026
Verified

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
Verified

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
Verified

10/10 Excellent

Vicente

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

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
Verified

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
Verified

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
Verified

8/10 Good

Matthew

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

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

6/10 Okay

James

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

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
Verified

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
Verified

10/10 Excellent

Laura

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

Great room and stay!

Our stay was great! We were coming into town to see family and needed a place to stay. It worked out perfectly.
Stayed 1 night in Nov 2023
Verified

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
Verified

10/10 Excellent

DAMEION

Liked: Cleanliness, staff & service, property conditions & facilities
Have stayed here several times. Is safe and clean. Walking distance to dining.
Stayed 1 night in Nov 2023