Red Roof Inn & Suites Chestertown

Property class: 2

Choose dates to view prices

Red Roof Inn & Suites Chestertown provides amenities like laundry facilities and a fireplace in the lobby. Guests can connect to free in-room WiFi.

Reviews

7.2 out of 10
Good

Popular amenities

  • Pet friendly
  • Free WiFi
  • Air conditioning
  • Laundry
  • Housekeeping
The current price is AED 264
AED 294 total
includes taxes & fees
1 Nov - 2 Nov

Room options

Available filters for rooms
Showing 4 of 4 rooms

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

A hotel room with a bed, a couch, a painting, and a window with curtains.

Superior Room, 1 King Bed, Accessible, Non Smoking

8.0 out of 10
Very good
(13 reviews)
  • 39 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed

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

A hotel room with a bed, a couch, a painting, and a window with curtains.

Superior Room, 1 King Bed, Accessible, Non Smoking

7.4 out of 10
Good
(13 reviews)
  • 39 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed

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

A hotel room with a bed, a couch, a painting, and a window with curtains.

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

7.2 out of 10
Good
(23 reviews)
  • 39 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Suite, Multiple Beds, Non Smoking

A hotel room with a sofa, two beds, a painting, and a lamp.

Suite, Multiple Beds, Non Smoking

8.2 out of 10
Very good
(22 reviews)
  • 42 sq m
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed

About the neighborhood

Located in Chestertown, Red Roof Inn & Suites Chestertown is in the city center. 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 Chesapeake Bay and Rolling Road Park. 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

  • A field of soybeans with a barn and silos in the background.
    Washington College
    8 min walk - 0.7 km
  • Rolling Road Park
    16 min walk - 1.4 km
  • Larrabee Arts Center
    18 min walk - 1.6 km
  • Chestertown Dog Park
    2 min drive - 1.4 km
  • Chestertown Farmers Market
    2 min drive - 2.8 km

Getting around

  • Baltimore Washington Intl. Airport (BWI)
    80 min drive

Restaurants

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

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 TV in the lobby, an elevator, and free newspapers
    • A vending machine, a 24-hour front desk, and coffee/tea in the lobby
    • 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

Similar properties

A hotel lobby with a fireplace, seating area, and a television.
Comfort Inn & Suites Chestertown
Chestertown
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
8.6 out of 10, Excellent, 994 reviews
The price is AED 361
AED 401 total
includes taxes & fees
15 Nov - 16 Nov
Comfort Inn & Suites Chestertown
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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 24 October 2026, prices found for a 1-night stay for 2 adults at Red Roof Inn & Suites Chestertown on 1 November 2026 start from AED 264, 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

Red Roof Inn & Suites Chestertown Reviews

7.2

Good

7.2

Cleanliness

8.6

Location

7.8

Staff & service

6.6

Property conditions & facilities
Rating 10 - Excellent. 147 out of 511 reviews
Rating 8 - Good. 148 out of 511 reviews
Rating 6 - Okay. 101 out of 511 reviews
Rating 4 - Poor. 65 out of 511 reviews
Rating 2 - Terrible. 50 out of 511 reviews

Reviews

Verified review

6/10 Okay

Liked: Staff & service
Easy check-in & out. Convenient parking. Room was clean, though there were stains on loveseat, sheets, comforter (look like they’d been there for awhile; washed & put back on).
Stayed 1 night in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Perfect for an overnight trip, staff was very helpful.
Stayed 1 night in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Big room,very comfortable bed,direct tv….pool was out of order,apparently has been for quite a while…..enjoyed our stay😀
Stayed 1 night in Jul 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, property conditions & facilities
Overall the stay was fine. Front desk staff was nice and check in was easy. Issues with the room: It was warm, dank and musty when we checked in. Got a little better after we had the AC on for a while, though still didn't smell great. Noticed the carpeting by the window / AC was very damp, which may explain the mustiness. Also needed a blanket and at least 2 more pillows. Regards, M. Alford
Stayed 1 night in Sep 2026
Verified review

10/10 Excellent

Liked: Staff & service
Vending machines were out of order, only ice machine was on first floor. Otherwise it was as expected for a red roof inn and last minute booking. Our neighbors had 4 young children that were very loud and running up and down the hallway when I first arrived but they were surprisingly calm later that evening so wasn’t an issue. Over all stay was fine and I accomplished what I came there for. Breakfast would be a huge plus and of they reopened the pool that’s been closed since Covid would certainly make for a much better review. Staff was amazing as always. Friendly and accommodating.
Stayed 1 night in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
front desk was very helpful and nice. Room was very clean and overall had a goodnight sleep
Stayed 1 night in May 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

8/10 Good

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

2/10 Terrible

Disliked: Cleanliness, amenities, property conditions & facilities
Staff was pleasant and room was clean… but the shower/bathroom was awkward… shower curtain hung to allow no room to move around. Common areas were very dusty and vending machines not operable. Outside was very full of weeds. We booked online and didn’t expect these conditions.
Stayed 1 night in May 2026
Verified review

10/10 Excellent

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

10/10 Excellent

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

10/10 Excellent

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 review

8/10 Good

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

10/10 Excellent

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 review

8/10 Good

Liked: Cleanliness, staff & service
Disliked: Property conditions & facilities
The price was very good. The room was clean and spacious. There were a few maintenance issues. Several light bulbs were burned out, the hair dryer did not work, the closet door was off its track, and the Satellite TV was not working. The staff were helpful but unsuccessful in programming the TV. For what I needed, a clean room to sleep, it was alright. The room had a microwave, fridge, and coffee maker all of which worked. The hot water was great and good pressure. I suspect the next time I stay there, these issues will be fixed.
Stayed 1 night in May 2026
Verified review

10/10 Excellent

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.
Stayed 2 nights in Mar 2026
Verified review

6/10 Okay

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 review

8/10 Good

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

10/10 Excellent

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 review

6/10 Okay

Liked: Staff & service
Disliked: Cleanliness, amenities, property conditions & facilities
The AC unit was on its last legs. The security latch was broken. The bathroom was in fair condition, at best. The bathroom door latch and knob were broken. No housekeeping. 1 towel, and all the linen was grayish. Elevators were dirty. Hallways were dirty. There was a wrecked car up on jacks in the parking lot. The staff was nice, and helpful. I’d stay again, alone, but not with my wife. It was affordable and that serves a segment that I understand.
Stayed 3 nights in May 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

8/10 Good

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