Is parking available at the property?

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

Does the hotel allow pets?

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.

What are the check-in and check-out times?

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.

What accessibility features are available for guests with disabilities?

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

What is the location of the hotel in relation to key landmarks?

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.

What are the policies for guests staying with children?

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

Red Roof Inn & Suites Chestertown

Average nightly price at Red Roof Inn & Suites Chestertown by month, last 12 months (USD)
Month	Average price
January	$65
February	$63
March	$73
April	$68
May	$76
June	$69
July	$68
August	$66
September	$73
October	$83
November	$81
December	$68

What guests think

Across the reviews for Red Roof Inn & Suites Chestertown, guests often find basic, budget-friendly stays with generally clean, spacious rooms and comfortable beds, but the aging property shows wear, frequent maintenance issues, and inconsistent experiences across areas.

Common problems include noisy or faulty HVAC, weak or missing hot water or pressure, broken fixtures, and stained carpets or musty odors, especially in hallways. Service is often friendly and helpful, though some guests mention slow or absent front desk coverage and understaffing. Location is convenient for Washington College and nearby dining, but amenities are limited, with the pool closed and no breakfast. Expect a no-frills, pet-friendly stay.

Facilities

Cleanliness

Rooms

Service

Location

Dining

Was this helpful?

AI-generated summary based on recent guest reviews

Facilities

Facilities are limited: the pool is often closed, ice machines and vending are sometimes unavailable, and guests note occasional elevator or equipment issues. Pet-friendly policies are a plus.

Related guest reviews

6

lisa

Feb 2, 2025

·

Stayed 2 nights

The building is dark/isn't well light in the lobby. Elevator wasn't working. But room was very clean.

10

Linda

Aug 15, 2024

·

Stayed 2 nights

Property was very nice. The pool was not open again. Hotel has no breakfast.

6

Kimberly

Oct 16, 2024

·

Stayed 1 night

Its an older property with much needed TLC overdue. Check in was smooth and without difficulty. Front desk was friendly. Luggage dolly was on the brink of falling apart. 3rd floor was pungent of marijuana. Room was fairly clean. No key to safe. Thin inner spring mattresses. Clean bedding. AC/HEAT was efficient. Bathroom defnitely needed more time from housekeeping as there was still some debris from a previous guest under the bathroom vanity. Didnt shower there but sink had hot water. Mini coffee maker worked. TV worked. Remote was tempermental. Overall what ive come to expect from red roof properties.

10

lisa

Oct 6, 2025

·

Stayed 2 nights

Wish they had the pool open. The staff is great here and very helpful.

8

Gale

Jul 28, 2025

·

Stayed 1 night

Did not like lack of vending services

6

Frank

Jul 10, 2023

·

Stayed 1 night

very pet friendly/

8

Katherine E

Sep 26, 2023

·

Stayed 1 night

The property has a very distinct smell in the halls. Not in the lobby or rooms. The pool is shut down indefinitely. Several items in the room were in disrepair and needed attention. I think we will plan our stay fo rone of the other hotels in the area next time

8

Richard

Jan 18, 2025

·

Stayed 1 night

What I linked- see above. No working ice machine in the Red Roof Inn on any floor. We were told that the ice machine had not been working for sometime.

8

Brigid

Nov 5, 2024

·

Stayed 2 nights

Room was ok, needed a little maintenance and TLC but was clean. Pool was closed indefinitely, and only 1 ice machine for the whole hotel. Doesn't appear owners are putting much $ into the place to keep it up.

8

Cynthia

May 31, 2024

·

Stayed 1 night

Expensive for the condition of the place but reasonably clean (likely due to big event in town). Bathroom door wouldn't close. The outside, lobby, carpet is okay but worn. No food available, not even in vending machine. Pool out of commission. But the location in general is nice, fairly quiet.

Was this helpful?

AI-generated summary based on recent guest reviews

Cleanliness

Cleanliness feedback is mixed. Rooms and linens are frequently described as clean, but stained carpets, musty odors, and occasional bathroom grime or mildew recur, especially in common areas.

Related guest reviews

10

Anne

Jun 16, 2025

·

Stayed 1 night

Great chain. The only issue is floors are not very clean. If you can't steam-wash carpets often best not to have them. Bathroom floor is sticky. But room is large and comfortable, staff very pleasant.

6

Allen

Oct 10, 2025

·

Stayed 1 night

Food stains on the carpets, spots throughout the carpets in commons and in rooms.

6

Neil

May 5, 2025

·

Stayed 1 night

Most of the previous reviews were correct; the property is dated, run down, and dark, but the linens were clean, the bathroom fixtures were newer, and the water pressure good. Most of the problem was just the age of the property; the carpet is dark and has a musty odor as though it hasn't been changed (ever?). The hair drier fell off the bathroom wall (with screws and all), partly because the bathroom door doesn't close. The wall behind the door had a huge gash where the handle hits it. The TV cable worked well(!), but the picture was truncated. The staff is very pleasant and are definitely trying their best, but we only ever saw one person at a time working.

6

Kelly

Nov 8, 2024

·

Stayed 1 night

Sadly , like so many business they were very short staffed. I literally had to track someone down when it came time to check out. The room itself wasn’t horrible but the carpeting in the common area ( the hallway) was so dirty and stained. The bathroom in our room was a completely different story. It appeared to possibly be in mid renovation. The sink was attached to the wall with only an all metal brace. Old fixture mountings still remained. The shower had a fold up seat that was covered in black mildew. Just awful.

8

Kevin

Dec 14, 2025

·

Stayed 1 night

Very clean. Pets allowed.

6

Richard C

Oct 14, 2025

·

Stayed 3 nights

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.

4

Nancy

Sep 29, 2025

·

Stayed 1 night

Staff was not welcoming or accommodating. Very dirty facility, not only the rooms but communal areas. Very outdated decor and furnishings. Should not be charging over $100 er night for such accommodations.

10

Vincent

Nov 20, 2025

·

Stayed 1 night

room was clean but the shower curtain was in tatters. multiple rings torn off

6

jeffrey

May 2, 2025

·

Stayed 3 nights

The property was dated and dirty

8

Robert

Jul 26, 2025

·

Stayed 1 night

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.

Was this helpful?

AI-generated summary based on recent guest reviews

Rooms

Rooms are generally spacious with comfortable beds, but the decor is dated. Guests report recurring maintenance problems such as noisy or weak A/C, poor water pressure or hot water interruptions, loose or broken fixtures, and inconsistent in-room amenities like TV size.

Related guest reviews

4

Bradley

Mar 23, 2025

·

Stayed 1 night

TV was to small and it says online 43 inch tv. No, 23 maybe.

6

Dale

Mar 3, 2025

·

Stayed 2 nights

Very loud heating unit in the room

4

Marina

Sep 29, 2024

·

Stayed 1 night

Close by the event I was going to. My room had a closet and the the sliding doors were hanging against eachother out of their rail. The curtain hanger was coming out of the ceiling and the airconditioner started to come out of the wall. I can go on ,.

6

Diana

Jun 10, 2024

·

Stayed 4 nights

Showing signs of age. Light switch, hair dryer, ac work, but are a bit wonky. Water pressure poor; shower head just dribbled in some settings. When I asked about maintenance, it seems there is no one on staff who can fix things. Won’t go back, especially since there is a newer, nicer hotel next door. Red Roof’s only apparent advantage is that it’s considerably less expensive.

4

Larry

Jul 19, 2025

·

Stayed 1 night

No water pressure. AC not working. Hair dryer not working. Comfortable bed

10

Marie Paz

Jul 21, 2025

·

Stayed 1 night

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.

10

Kellie

Sep 27, 2025

·

Stayed 1 night

Room temperature was good. Room was also very spacious and clean.

6

Everett

Aug 10, 2025

·

Stayed 1 night

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.

8

Michael

Jul 9, 2025

·

Stayed 1 night

Pretty decent room size. AC didn't work very well, but we survived. Good experience overall.

8

Robert

Jul 26, 2025

·

Stayed 1 night

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.

Was this helpful?

AI-generated summary based on recent guest reviews

Service

Service is mixed: many guests praise friendly, helpful staff, while others report slow check-in, absent front desk coverage, or curt interactions. Staffing appears thin at times.

Related guest reviews

8

Matthew

Nov 6, 2024

·

Stayed 1 night

Staff was very friendly

10

DAMEION

Jan 1, 2024

·

Stayed 2 nights

Front desk staff was very helpful and friendly. Check in was quick and without a hitch. Doing some renovations but is fine for a stay

4

Susan

Sep 7, 2024

·

Stayed 1 night

Terrible staff attitudes. Crappy room - fridge, ac, tv didn’t work. Whole place stunk. Sorry, we needed a pet friendly for our puppy and we knew it’s not a 3-4 star place but I can’t wait to get home to shower. P.S. I never write a review….

8

michelle

Jan 25, 2025

·

Stayed 1 night

This property was def. Off season. It was very low key, the room was big and clean, hotel understaffed but I think it was just the time of year. Overall would for sure stay here again.Big value for the cost

6

Elaine

Nov 5, 2023

·

Stayed 1 night

Arrived to check in. Not greeted at all by desk clerk. She handled our check in quickly but not friendly. Lobby was ok…. Seemed clean and was somewhat attractive. Halls to rooms had very dirty, stained carpets. Some yellow tape in areas blocking off what May have been the gym or pool. Room smelled weird… not sure what it was.. maybe old smoke . Rugs in room were ok. Bed very comfortable and clean. We stayed in king room.. sofa was worn and even had foam showing through torn seams. Coffee, refrigerator and microwave in room . Bathroom provided one small towel, one hand towel and one washcloth per person. Friend we were traveling with went to ask for more as there were 4 people staying in her room and was screamed at by the clerk. Floor was dirty looking , although I tried to wipe it up and it didn’t come up. It was only around the tub area. The place was quiet. No clocks in room. The place just didn’t feel clean or comfortable . We only stayed one night. When we return next year for the conference, I think we will either bring our camper or pay the extra and stay next door. It was only a block to our conference, so was very convenient!

10

DAMEION

Jan 21, 2025

·

Stayed 1 night

Have stayed here several times. Nice staff and clean rooms. Can walk for food

6

Kelly

Nov 8, 2024

·

Stayed 1 night

Sadly , like so many business they were very short staffed. I literally had to track someone down when it came time to check out. The room itself wasn’t horrible but the carpeting in the common area ( the hallway) was so dirty and stained. The bathroom in our room was a completely different story. It appeared to possibly be in mid renovation. The sink was attached to the wall with only an all metal brace. Old fixture mountings still remained. The shower had a fold up seat that was covered in black mildew. Just awful.

10

Christine

Apr 30, 2023

·

Stayed 1 night

The staff that checked us in, don't remember her name was so helpful because a tree went down on the highway and I couldnt get to the hotel. She gave me alternate directions and got me there safe in the rain! Ty from an out of towner!!!

10

Maria

Aug 1, 2025

·

Stayed 3 nights

Great service

6

Ngoc

Apr 5, 2025

·

Stayed 1 night

Granted we checked in at 11pm on a Friday night, but there didn’t seem urgency in getting us registered quickly. The hotel is definitely well worn, but generally clean. Furnishings were dated and amenities sparse. Upon checking into our room, walking up to the couch, I noticed a large piece of white paper/cloth next to it. It was an easy task for housekeeping, who chose to ignore it. This made me worry about the overall level of cleanliness in the room. We chose Red Roof Inn due to proximity to Washington College and the lack of hotel options in the area. For $125/night, it wasn’t dirt-cheap, but I won’t be returning to this hotel in the future. It could definitely use a refresh.

Was this helpful?

AI-generated summary based on recent guest reviews

Location

Convenient for Washington College and town services, with dining options within walking distance. Generally easy to access and fairly quiet.

Related guest reviews

10

Bonney

Oct 29, 2023

·

Stayed 2 nights

Excellent value for the price. Accessible location, very quiet, clean, everything we needed was in our rooms.

10

Gary

Apr 20, 2025

·

Stayed 1 night

Easy to get to, food all around!

10

DAMEION

Jan 21, 2025

·

Stayed 1 night

Have stayed here several times. Nice staff and clean rooms. Can walk for food

10

Vicente

May 19, 2025

·

Stayed 1 night

Very nice location and area

10

alaiyah

May 29, 2024

·

Stayed 4 nights

nice hotel. helpful staff. stores and dining are walkable distances.

10

DAMEION

Nov 22, 2023

·

Stayed 1 night

Have stayed here several times. Is safe and clean. Walking distance to dining.

6

Eric

Jul 21, 2025

·

Stayed 1 night

Good location.

8

Joseph

Apr 13, 2024

·

Stayed 1 night

This is a conveniently located and comfortable Inn/Hotel. It was perfect for a one night stay. The only deficit was the lack of a simple, continental breakfast room necessitating a walk to the local DD/Dunkin'.

6

katherine

Jul 27, 2023

·

Stayed 1 night

Beds and shower were fine. No sign visible from the main road so had to drive around a bit. "Sleeps 4" but there were only 3 towels and 1 cup. No breakfast but there is a DD handy.... not a destination, just a road stop so I'm not complaini g....

6

Eileen

Aug 12, 2023

·

Stayed 2 nights

Close to all our needs.

Was this helpful?

AI-generated summary based on recent guest reviews

Dining

On-site dining is very limited, with no breakfast provided and at times no lobby coffee. Expect to go off-site for food and drinks.

Related guest reviews

6

JoAnnie

Oct 11, 2023

·

Stayed 2 nights

Property location and rooms were okay. Nothing like what was shown on Expedia website. Furthermore, it said complimentary breakfast at time of booking and no food was provided at the property. Overall I rate this property a 3.

10

Linda

Aug 15, 2024

·

Stayed 2 nights

Property was very nice. The pool was not open again. Hotel has no breakfast.

4

Michael

Jun 3, 2025

·

Stayed 3 nights

Carpet begs to be put out of its misery. Really gross in lobby. And no breakfast at all? Cheap!

8

Richard

Jun 17, 2023

·

Stayed 1 night

The dining options were very limited.

6

sal

Jun 2, 2024

·

Stayed 2 nights

Friendly staff. Not super clean room Strong shower a plus Toilet water too high to seat; hand gets wet as a result No breakfast or even coffee a big negative

8

Joseph

Apr 13, 2024

·

Stayed 1 night

This is a conveniently located and comfortable Inn/Hotel. It was perfect for a one night stay. The only deficit was the lack of a simple, continental breakfast room necessitating a walk to the local DD/Dunkin'.

4

debra

Jun 2, 2025

·

Stayed 1 night

Convenient to Chestertown. No breakfast. No regular coffee in room. No creamer or sugar. Couch and floor dirty

10

Laurie

May 15, 2023

·

Stayed 1 night

The check in staff was terrific & was able to change rooms quickly as I had mistakenly booked a rm. w/one bed instead of 2. Explained why there was no breakfast area & their inability to change the website. We were fine as there was coffee maker in room :-)

10

Milton

Nov 10, 2024

·

Stayed 2 nights

Comfortable room and fair price for the room size. Very clean. Bathroom was nice but had a broken wall mounted hair dryer and the bathroom door did not latch closed so it stayed open about an inch. Front desk was businesslike but not the least bit friendly. There is no breakfast or even coffee offered. You have to go out for breakfast. Excuse was not since Covid. That adds another $20 per couple for breakfast to the room price.

8

Cynthia

May 31, 2024

·

Stayed 1 night

Expensive for the condition of the place but reasonably clean (likely due to big event in town). Bathroom door wouldn't close. The outside, lobby, carpet is okay but worn. No food available, not even in vending machine. Pool out of commission. But the location in general is nice, fairly quiet.

Was this helpful?

AI-generated summary based on recent guest reviews

Su	Mo	Tu	We	Th	Fr	Sa
				1	2	3
4	5	6	7	8	9 $125	10 $131
11 $67	12 $68	13 $68	14 $68	15 $70	16 $101	17 $102
18 $68	19 $69	20 $70	21 $69	22 $67	23 $101	24 $102
25 $67	26 $68	27 $67	28 $68	29 $69	30 $101	31 $101

Su	Mo	Tu	We	Th	Fr	Sa
1 $70	2 $68	3 $67	4 $67	5 $68	6 $106	7 $101
8 $67	9 $68	10 $68	11 $68	12 $68	13 $101	14 $102
15 $68	16 $70	17 $69	18 $71	19 $69	20 $102	21 $101
22 $68	23 $68	24 $68	25 $69	26 $67	27 $105	28 $99
29 $68	30 $68

Red Roof Inn & Suites Chestertown

Prices for Red Roof Inn & Suites Chestertown

Monthly average prices

About this property

Location

Room options

Standard Suite, 1 King Bed with Sofa Bed

Superior Room, 1 King Bed, Accessible

Suite, Multiple Beds

Guest reviews of Red Roof Inn & Suites Chestertown

What guests think

Property Policies

Check-in instructions

Security deposit

Good to know

Optional extras

FAQs about Red Roof Inn & Suites Chestertown

Prices for upcoming dates