Red Roof Inn & Suites Chestertown
3.6
Good(319 Reviews)Hotel in Chestertown, MD
Reasons to book
Includes essentialsKitchen or Kitchenette, Air conditioner, Internet / Wifi and more
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this hotel
Hotel in Chestertown with free parking
This hotel features coffee/tea in a common area, laundry facilities, and a 24-hour front desk. Free WiFi in public areas and free self parking are also provided. Additionally, free newspapers, a lobby fireplace, and a vending machine are onsite.
Change of towels is available on request.
Red Roof Inn & Suites Chestertown offers 53 air-conditioned accommodations with coffee/tea makers and hair dryers. 43-inch flat-screen televisions come with premium cable channels and pay movies.
This hotel features coffee/tea in a common area, laundry facilities, and a 24-hour front desk. Free WiFi in public areas and free self parking are also provided. Additionally, free newspapers, a lobby fireplace, and a vending machine are onsite.
Change of towels is available on request.
Red Roof Inn & Suites Chestertown offers 53 air-conditioned accommodations with coffee/tea makers and hair dryers. 43-inch flat-screen televisions come with premium cable channels and pay movies.
This Chestertown hotel provides complimentary wireless Internet access. Business-friendly amenities include desks and desk chairs; local and long-distance calls are complimentary (restrictions may apply). Additionally, rooms include irons/ironing boards and complimentary toiletries. Change of towels and change of bedsheets can be requested. Housekeeping is provided daily.
Amenities
Air conditioner
Kitchen or Kitchenette
Internet / Wifi
Parking
Laundry
TV
Map of Chestertown, MD
Available Rooms
Superior Room, 1 King Bed, Accessible, Non Smoking
1 King • 419 ft²
Sleeps 2
You'll be directed to Expedia.com for availability & pricing
Superior Room, 1 King Bed, Accessible, Non Smoking
1 King • 425 ft²
Sleeps 2
You'll be directed to Expedia.com for availability & pricing
Standard Suite, 1 King Bed with Sofa bed, Non Smoking
1 King • 1 Sofa • 419 ft²
Sleeps 4
You'll be directed to Expedia.com for availability & pricing
Suite, Multiple Beds, Non Smoking
2 Queen • 1 Sofa • 450 ft²
Sleeps 6
+
You'll be directed to Expedia.com for availability & pricing
$$$$
Reviews
3.6
Good(319 Reviews)3.6
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.
3.6
Stayed one night for the Sultana Downrigging Festival. Just needed a place to sleep. Served our needs. Bathroom was nice, good shower.
3.6
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.
3.6
The attendant was on break when I came into the lobby but the wait was short. I had driven in 7.5 hours from NC and just needed a place to get a few hours sleep and this stay met that requirement. Clean and safe.
3.6
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.
3.6
The bed was very comfortable, staff lovely, room is spacious. There was coffee in the room but none in the lobby. It would be nice to have coffee with cream/milk options.
3.6
There was an ironing board in the room but no iron in room or on property. Does not make sense. The bathroom door was missing the exterior door knob. The outlet in the bathroom did not work.
3.6
Gross. Shame on you. Place is fast falling into a dump. Dont put college student parents through this rip off hell hole.
3.6
Property was very nice.
The pool was not open again.
Hotel has no breakfast.
3.6
Great Place to stay
3.6
It was very quiet. The room was clean and the bed was comfortable. I think its an older building so it could use a little love.
3.6
Carpeting needs serious cleaning.
Bed needs new mattress.
Needs thorough cleaning.
Paid close to $200 for 1 night and would have been better off sleeping in a tent!
3.6
Air didn't work well. 1st room smelled. Not good for what they charge.
3.6
Person checking me in was not very cordial; Other staff folks were pleasant; nice to have daily housekeeping; sign for motel was not visible (actually went to the next door motel); room size was excellent; hall carpet needs replacing
3.6
The bed and pillow were extremely uncomfortable. The bed was lumpy and the pillow was so large and firm that my neck was at an uncomfortable angle no matter my position. I had gone to bed about 11pm and by midnight, I realized there was no hope of getting any sleep, so I checked out. Never again.
3.6
Not exceptional, but clean.
3.6
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.
3.6
Not bad, just ok
3.6
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
3.6
Front desk staff: no uniform or name tag identifying who they were. Not very friendly. Didn’t tell basic stuff about the hotel (yes it was on the wall, but still) or area.
3.6
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.
3.6
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
3.6
nice hotel. helpful staff. stores and dining are walkable distances.
3.6
The bed was made up with a flat sheet. So the cover where off the bed the whole weekend. Besides that everything was 3 stars.
3.6
Property was OK, would stay again
3.6
Sometimes, you don’t need a fancy place; just a clean place. That’s what this is. Maybe there weren’t the newest finishes, but we really appreciated having the extra pull-out couch and space in the room. It was perfect for traveling with my 3 teenagers.
3.6
thanks
3.6
Hotel was a hotel… hated the small toilets… if you go to wipe your hand will end up touching the water.. yuck! If you’re a man and have to poop…. hold your junk up!!!
3.6
DO NOT STAY HERE!! Having stayed in this rundown, moderately clean motel before (I have a kid at WashColl), I called ahead to say I’d be checking in at 11:30pm (driving from afar to move kid out in am) and to please make sure I was in a clean room with extra blankets. When I arrived there were maybe 3 other cars in the parking lot, so the motel was presumably quite empty. The room I was given was ‘clean’ but as gross and run down as to be expected. At about 1:30am I awoke to the sound of water dripping loudly in the room. I discovered a leak in the ceiling mostly shielded by the drapes. The ceiling stain was about 8 inches in diameter was black and moldy and rotted and quarter size drops were coming in from the rain outside. So this was an ongoing problem. It would take quite some time and neglect to create a problem of that size. I called down and asked to be moved. The nice young man at the front desk was apologetic and accommodating, getting me a room down the hall. I packed up and moved and tried to go back to bed. In the morning at check out I asked if the hotel would be refunding me or if I needed to contact Expedia. The women scoffed at me and said “we moved your room and you spent the night, so no.” I showed her the picture of the disgusting health hazard of a ceiling and pointed out that I didn’t have a lot of options at 2 in the morning. She could not have cared less. Please don’t ever make the mistake of staying here. It’s beyond foul.
3.6
The place was a total pit. There was no room service, . They had a sign in lobby that said if you want anything call the desk. They will dig it out for you and you can come n get it.Carpet was soo dirty you couldn’t tell what original pattern was. Soda machine didn’t work..Hotel smelled like pot.
3.6
The hotel was adequate for what we needed. Just a place to sleep. My older children were a floor above us and the whole 3rd floor and elevator reeked of pot. Very dated. Elevator inspection expired 6 years ago. Other than that, it was adequate.
3.6
From the first night i arrived there was no flow of hot water to the tub. There was a trickel of water thats it i called down to front desk and the lady said it wouldbe the following day before maintenance could come fix. When i arrived back later saturday afternoon, still now hot water to the tub. Sso i xhecked out explained to frint desk what was going on ,tje owner or manager of the hotel said no refund because it was at 4 oclock at this point. I will never stay at red roof in. Any where again. I will ne calling corporate monday morning the 29th of april
3.6
Chestertown is a quiet quaint little town. We will be returning but not staying at the Red Roof Inn. Old and worn down, the bathroom smells like urine, light switches and door frames filthy. There is no fan in the bathroom. There’s a coffee pot but no mugs or paper/plastic cups. Only a bar of sample soap and tube of shampoo in the bathroom, no tissues. Very thankful we had toilet paper. There were 2 towels and 2 wash cloths, we shared a hand towel. Oh, and the TV didn’t work. We are glad we are only here for one night! There was a staff member here because my husband checked us in around 7pm, I returned around 9 pm there was no one at the desk but they must have been watching a camera from another room because they came out shortly and then immediately retreated. Didn’t seem very secure. When my husband returned at 10 there was no sign of any attendant. We booked through Expedia, not sure if they have nicer rooms available if you book through their website but disappointed and will not be returning.
3.6
Problem with the door to the room and the door to the bathroom not closing.
3.6
The air conditioner was very noisy woke me up every time it went on about every 10 minutes also had a strange smell, and my American Express card was denied for no reason
3.6
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'.
3.6
Bad
3.6
Need to pick up the grounds but overall satisfied
3.6
Room was not clean at all.
3.6
The room was very nice; great location. I am local and booked this so I could attend friends' gatherings without having to drive but upon arrival about 2 hours before normal check-in time was blown-off by front desk person who said they could not get in me in any earlier than 3PM because they had been completely full the night previous even though I was the only car in the lot and there was no sign of anyone doing housekeeping. I left and returned at 4:30 to find a sign saying they were on a "lunch" break; he arrived back about 10 minutes after I arrived. Both folks were very polite. Room was very nice.
FAQs
How much does this hotel cost compared to others in Chestertown?
The average price for a rental in Chestertown is $318 per night. This rental is $191 less expensive than the average.
Is parking included with this hotel?
Yes, parking is listed as an amenity at Red Roof Inn & Suites Chestertown. For more information, we encourage you to contact the property about where to park.
Is there a pool at this hotel?
We didn’t find pool listed as an amenity for this hotel. It may be worth double checking if a pool is important for your stay.
Is Red Roof Inn & Suites Chestertown pet friendly?
Unfortunately, this hotel is not pet-friendly. Try searching again and filter for "Pets Allowed"
What amenities are available at Red Roof Inn & Suites Chestertown?
We found 6 amenities for this rental. This includes air conditioner, kitchen or kitchenette, internet / wifi, parking, and laundry.
Explore similar vacation rentals in Chestertown
Explore all rentals in Chestertown
Comfort Inn & Suites Chestertown
Hotel
in Chestertown2star
2 queen beds
Pets allowed · Kitchen or Kitchenette · Air conditioner
Looking for a memorable stay in Chestertown? Our Hotel might just be what you're looking for. Enjoy amenities including Air conditioner, Internet / Wifi and Laundry, and more during your stay.
$$$$
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
House
in Chestertown8 guests · 4 bedrooms · 3 baths
Garden · Kitchen or Kitchenette · Air conditioner
Looking for the perfect place to call home during your trip to Chestertown? This House offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Comfort Inn & Suites Chestertown
Vacation rental
in ChestertownAir conditioner · Internet / Wifi · Parking
The best choice in Chestertown for Vacation rental, for $186 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Pet-friendly Home on Chester River w/ Dock!
Cottage
in ChestertownPool · Pets allowed · Kitchen or Kitchenette
Are you ready to indulge in a relaxing getaway? Our Cottage in Chestertown has everything you need for a rejuvenating stay. Treat yourself to Pet-friendly Home on Chester River w/ Dock!'s exceptional amenities, such as Air conditioner, Internet / Wifi and Pets allowed.
$$$$
Pet-Friendly Home on Chester River w/ Dock!
House
in Chestertown14 guests
Garden · Pool · Pets allowed
Looking for the perfect place to call home during your trip to Chestertown? This House offers a comfort and style with top-notch amenities, including Air conditioner, Internet / Wifi and Pets allowed, and more.
$$$$
Carriage House Hideaway in Middle of Chestertown
Apartment
in Chestertown2 guests · 1 bath
Garden · Pets allowed · Kitchen or Kitchenette
Looking for the perfect place to call home during your trip to Chestertown? This Apartment offers a comfort and style with top-notch amenities, including Air conditioner, Internet / Wifi and Laundry, and more.
$$$$
Country Estate in Historic District
House
in Chestertown10 guests · 5 bedrooms · 4 baths
Garden · Pets allowed · Kitchen or Kitchenette
This inviting House in Chestertown can fit your needs for many types of vacations, at $783 per night.
$$$$
Start earning One Key rewards
Circa 1900 Home in the Heart of Historic Downtown Chestertown
House
in Chestertown6 guests · 4 bedrooms · 2 baths
Garden · Kitchen or Kitchenette · Air conditioner
Top rated
Discover the beauty of Chestertown with a stay at Circa 1900 Home in the Heart of Historic Downtown Chestertown, a top rated House with amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Driftwood Inn
Motel
in Chestertown1 queen bed
Pets allowed · Kitchen or Kitchenette · Air conditioner
This inviting Motel in Chestertown can fit your needs for many types of vacations, at $103 per night.
$$$$
Start earning One Key rewards
Historic Stepne Manor on Maryland's Eastern Shore
House
in Chestertown15 guests · 5 bedrooms · 4 baths
Garden · Pets allowed · Kitchen or Kitchenette
Discover the beauty of Chestertown with a stay at Historic Stepne Manor on Maryland's Eastern Shore, a top rated House with amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Historic Downtown Garden Oasis with Private Patio
Apartment
in Chestertown2 guests · 1 bedroom · 1 bath
Garden · Kitchen or Kitchenette · Air conditioner
Apartment in Chestertown, for $272 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)
$$$$
Victorian Hideaway: Beautiful Exterior, Modern interior
House
in Chestertown8 guests · 4 bedrooms · 3 baths
Garden · Kitchen or Kitchenette · Air conditioner
Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Chestertown, at $993 per night for your next great vacation.
$$$$
Carriage House Hideaway In Center of Chestertown
Apartment
in ChestertownGarden · Pets allowed · Air conditioner
Enjoy the best of Chestertown in our Apartment, Carriage House Hideaway In Center of Chestertown. A stunning property with amenities including Air conditioner, Pets allowed and Garden, and more.
$$$$
Red Roof Inn & Suites Chestertown
Vacation rental
in ChestertownAir conditioner · Internet / Wifi · Parking
Experience the best of Chestertown with this Vacation rental available for $128. This property is equipped with amenities including Air conditioner, Fireplace and Internet / Wifi, and more.
$$$$
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
House
in Chestertown14 guests · 6 bedrooms · 7 baths
Garden · Kitchen or Kitchenette · Air conditioner
This House for $2,060 in Chestertown, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Start earning One Key rewards
Newly restored apartment in the heart of Chestertown
Apartment
in Chestertown4 guests · 2 bedrooms · 1 bath
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
The best choice in Chestertown for Apartment, for $407 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
House
in Chestertown6 guests · 3 bedrooms · 3 baths
Garden · Kitchen or Kitchenette · Air conditioner
Experience the best of Chestertown with this House available for $340. This property is equipped with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Pet-Friendly Home on Chester River with Dock!
House
in ChestertownPool · Pets allowed · Kitchen or Kitchenette
Experience the best of Chestertown with this House available for $104. This property is equipped with amenities including Air conditioner, Internet / Wifi and Pets allowed, and more.
$$$$
2 Beds, 2.5 Baths, Perfect Downtown Location
House
in Chestertown4 guests · 2 bedrooms · 3 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Indulge in a peaceful retreat at 2 Beds, 2.5 Baths, Perfect Downtown Location, our elegant House in Chestertown. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown
House
in Chestertown8 guests · 3 bedrooms · 3 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
This House for $576 in Chestertown, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Start earning One Key rewards
Pet-Friendly Home on Chester River w/ Dock!
House
in Chestertown14 guests · 7 bedrooms · 5 baths
Garden · Pool · Pets allowed
The best choice in Chestertown for House, for $661 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Chestertown travel inspiration
Read our blogGuides
Top Things to Do in Miami: From Beaches to Culture
Guides
The Best Things to Do in Orlando: Attractions, Food, and Family Fun
Guides
Things to Do in Galveston, Texas
Guides
Top Things to Do in Myrtle Beach
Guides
Ski Trip Packing List: What to Bring Skiing or Snowboarding
Trends
VacationRenter Holiday Travel Trends 2023
Featured Rentals
Architectural Vacation Rentals: Experience the Beauty of Unique Properties
Featured Rentals
Sustainable and Eco-Friendly Vacation Rentals Around the World