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Comfort Inn & Suites Chestertown

2.5 star property
Guests start their day with complimentary coffee in the welcoming lobby, energize with a workout, and unwind by the fireplace near River Arts Chestertown.

Choose dates to view prices

Comfort Inn & Suites in Chestertown offers a warm atmosphere with a lobby fireplace and free full breakfast. Enjoy in-room WiFi, gym access, and a business center to stay productive. The attentive staff consistently earns positive reviews from visitors.

Reviews

8.6 out of 10
Excellent

Popular amenities

  • Pool
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
The current price is ￥16,061
￥17,828 total
includes taxes & fees
Feb 14 - Feb 15

Room options

Available filters for rooms
Showing 8 of 8 rooms

View all photos for Room, 1 King Bed, Accessible, Non Smoking (Accessible Tub)

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

Room, 1 King Bed, Accessible, Non Smoking (Accessible Tub)

8.8 out of 10
Excellent
(3 reviews)

Highlights

Air conditioning
Heating
Refrigerator
Flat-screen TV
Blackout drapes/curtains
Hydromassage showerhead
Hair dryer
Private bathroom
  • Sleeps 2
  • 1 King Bed

View all photos for Room, 2 Queen Beds, Accessible, Non Smoking (Accessible Tub)

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

Room, 2 Queen Beds, Accessible, Non Smoking (Accessible Tub)

8.8 out of 10
Excellent
(3 reviews)

Highlights

Air conditioning
Heating
Refrigerator
Flat-screen TV
Blackout drapes/curtains
Hydromassage showerhead
Hair dryer
Private bathroom
  • Sleeps 4
  • 2 Queen Beds

View all photos for Room, 2 Queen Beds, Accessible, Non Smoking (Roll-In Shower)

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

Room, 2 Queen Beds, Accessible, Non Smoking (Roll-In Shower)

Highlights

Air conditioning
Heating
Refrigerator
Flat-screen TV
Blackout drapes/curtains
Hydromassage showerhead
Hair dryer
Private bathroom
  • Sleeps 4
  • 2 Queen Beds

View all photos for Standard Room, 1 King Bed, Non Smoking

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

Standard Room, 1 King Bed, Non Smoking

8.0 out of 10
Very good
(16 reviews)

Highlights

Air conditioning
Heating
Refrigerator
Flat-screen TV
Blackout drapes/curtains
Hydromassage showerhead
Hair dryer
Private bathroom
  • Sleeps 2
  • 1 King Bed

View all photos for Standard Room, 2 Queen Beds, Non Smoking

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

Standard Room, 2 Queen Beds, Non Smoking

9.0 out of 10
Wonderful
(37 reviews)

Highlights

Air conditioning
Heating
Refrigerator
Flat-screen TV
Blackout drapes/curtains
Hydromassage showerhead
Hair dryer
Private bathroom
  • Sleeps 4
  • 2 Queen Beds

View all photos for Suite, Multiple Beds, Accessible, Non Smoking (Accessible Tub)

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

Suite, Multiple Beds, Accessible, Non Smoking (Accessible Tub)

10.0 out of 10
Exceptional
(1 review)

Highlights

Air conditioning
Heating
Refrigerator
Flat-screen TV
Separate bedroom
Blackout drapes/curtains
Hydromassage showerhead
Hair dryer
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed

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

Suite, 1 King Bed with Sofa bed, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board

Suite, 1 King Bed with Sofa bed, Non Smoking

7.6 out of 10
Good
(7 reviews)

Highlights

Air conditioning
Heating
Refrigerator
Flat-screen TV
Blackout drapes/curtains
Sofa bed
Separate bedroom
Hydromassage showerhead
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Suite, Multiple Beds, Non Smoking

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

Suite, Multiple Beds, Non Smoking

8.8 out of 10
Excellent
(9 reviews)

Highlights

Air conditioning
Heating
Refrigerator
Flat-screen TV
Separate bedroom
Blackout drapes/curtains
Hydromassage showerhead
Hair dryer
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed
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About the neighborhood

Located in Chestertown, Comfort Inn & Suites Chestertown is in the business district. 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 Betterton Beach and Eastern Neck National Wildlife Refuge. Don't miss out on a visit to Crumpton Auction. Spend some time exploring the area's activities, including winery tours. Visit our Chestertown travel guide
Map
21620, MD, Chestertown, 150 Scheeler Road

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
  • Rolling Road Park
    11 min walk - 1.0 km
  • Historical Society of Kent County Maryland
    3 min drive - 2.8 km
  • Garfield Center for the Arts at the Prince Theater
    3 min drive - 2.8 km
  • River Arts Chestertown
    3 min drive - 2.8 km

Getting around

  • Edgewood Station
    88 min drive
  • Baltimore, MD (MTN-Martin State)
    108 min drive

Restaurants

  • Milano's Pizzeria
    6 min drive
  • Royal Farms
    2 min drive
  • Dunkin
    5 min walk
  • Royal Farms
    5 min drive
  • McDonald's
    11 min walk

About this property

Comfort Inn & Suites Chestertown

Hotel near Washington College
Located close to River Arts Chestertown and Historical Society of Kent County Maryland, Comfort Inn & Suites Chestertown provides free full breakfast, laundry facilities, and a fireplace in the lobby. Stay connected with free in-room WiFi, and guests can find other amenities such as a gym and a business center.
Additional perks include:
  • A seasonal outdoor pool along with sun loungers and pool umbrellas
  • Free self parking
  • A vending machine, a banquet hall, and an elevator
  • Smoke-free premises, a TV in the lobby, and coffee/tea in the lobby
  • Guest reviews give top marks for the helpful staff
Room features
All 81 rooms offer comforts such as laptop-friendly workspaces and air conditioning, as well as perks like free WiFi. Guest reviews speak positively of the clean rooms at the property.
More amenities include:
  • Rollaway/extra beds (surcharge) and cribs/infant beds (surcharge)
  • Bathrooms with hydromassage showers and designer toiletries
  • 42-inch flat-screen TVs with premium channels
  • Wardrobes/closets, refrigerators, and microwaves

Similar properties

Lobby lounge
Red Roof Inn & Suites Chestertown
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
7.2 out of 10, Good, 427 reviews
The price is ￥11,115
￥12,337 total
includes taxes & fees
Feb 7 - Feb 8
Red Roof Inn & Suites Chestertown
Compare similar properties

Property amenities

Internet

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

Parking and transportation

  • Free self parking on site
  • Wheelchair-accessible parking and van parking available

Food and drink

  • Free full breakfast available 6:30 AM to 9:30 AM on weekdays and 7:00 AM to 10:00 AM on weekends
  • Coffee and tea in common areas

Things to do

  • Gym
  • Seasonal outdoor pool
  • TV in common areas

Family friendly

  • Crib (surcharge)
  • Fenced pool
  • In-room microwave
  • In-room refrigerator
  • Laundry facilities
  • Pool gate
  • Rollaway/extra bed (surcharge)
  • Seasonal outdoor pool

Conveniences

  • 24-hour front desk
  • Laundry facilities
  • Vending machine

Guest services

  • Housekeeping (daily)

Business services

  • Business center
  • Meeting room

Outdoors

  • Pool loungers
  • Pool umbrellas

Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • 4 accessible parking spaces
  • Assistive listening devices
  • Braille/raised signage
  • Elevator (36 inch wide door)
  • Handrails in stairways (36 inches high)
  • Lever door handles
  • Pool hoist on site
  • Stair-free path to entrance
  • Visual alarms in hallways
  • Well-lit path to entrance
  • Wheelchair accessible (may have limitations)
  • Wheelchair-accessible business center
  • Wheelchair-accessible concierge desk
  • Wheelchair-accessible gym
  • Wheelchair-accessible parking
  • Wheelchair-accessible path of travel
  • Wheelchair-accessible path to elevator
  • Wheelchair-accessible pool
  • Wheelchair-accessible public washroom
  • Wheelchair-accessible registration desk (36 inches high)
  • Wheelchair-accessible van parking

More

  • 3 floors
  • Banquet hall
  • Fireplace in lobby
  • Smoking not allowed

Room amenities

Bedroom

  • Bedsheets provided
  • Blackout drapes
  • Crib (surcharge)
  • Rollaway/extra bed (surcharge)

Bathroom

  • Bathtub or shower
  • Designer toiletries
  • Hair dryer
  • Hydromassage showerhead
  • Private bathroom
  • Shampoo
  • Soap
  • Toilet paper
  • Toothbrush and toothpaste (on request)
  • Towels provided

Entertainment

  • 42-inch flat-screen TV with premium satellite channels

Food and drink

  • Coffee/tea maker
  • Microwave
  • Refrigerator

More

  • Air conditioning (climate-controlled)
  • Desk
  • Free local calls
  • Heating
  • Iron/ironing board
  • Laptop workspace
  • Phone

Policies

Check-in

Check-in start time: 3:00 PM; Check-in end time: anytime
Early check-in subject to availability
Early check-in fee: USD 50.00
Contactless check-in available
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

Access methods

Staffed front desk

Pets

Pets allowed for an extra charge of USD 25 per accommodation, per night
Service animals are welcome, and are exempt from fees

Children and extra beds

Children are welcome
Children can stay for free if using existing beds when occupying the parent or guardian's room
Rollaway/extra beds are available for USD 15.0 per stay
Cribs (infant beds) are available for USD 15.0 per stay

Property payment types

Important information

Optional extras

  • Pet fee: USD 25 per accommodation, per night
  • Service animals are exempt from fees
  • Early check-in fee: USD 50.00 (subject to availability)
  • Crib (infant bed) fee: USD 15.0 per stay
  • Rollaway bed fee: USD 15.0 per stay

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
Cashless transactions are available
Safety features at this property include a carbon monoxide detector, a smoke detector, and window guards

We should mention

The seasonal pool will be open from June 21 to September 01
Pool access available from 8:00 AM to 8:00 PM
This property welcomes guests of all sexual orientations and gender identities (LGBTQ+ friendly)

Property is also known as

Holiday Inn Express Chestertown
Holiday Inn Express Hotel Chestertown
Chestertown Holiday Inn
Holiday Inn Chestertown
Holiday Inn Express Hotel And Suites Chestertown
Chestertown Holiday Inn
Holiday Inn Chestertown
Holiday Inn Express Hotel Suites Chestertown

Frequently asked questions

Does Comfort Inn & Suites Chestertown have a pool?

Yes, this property has a seasonal outdoor pool. Pool access is from 8:00 AM–8:00 PM.

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

As of Jan 27, 2026, prices found for a 1-night stay for 2 adults at Comfort Inn & Suites Chestertown on Feb 14, 2026 start from ￥16,061, 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.

Is Comfort Inn & Suites Chestertown pet-friendly?

Yes, pets are allowed at this property. There's a fee of USD 25 per accommodation, per night. Service animals are exempt from fees.

How much is parking?

Self parking is free at this property.

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

Check-in start time: 3:00 PM; Check-in end time: anytime. Early check-in is available for a fee of USD 50.00 (subject to availability).

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

Check-out is at 11 AM.

Where is Comfort Inn & Suites Chestertown located?

Situated in the historical district, this hotel is within 2 mi (3 km) of Washington College, Historical Society of Kent County Maryland, and River Arts Chestertown. Rolphs Wharf Marina and Cassinelli Winery and Vineyards are also within 12 mi (20 km).

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Reviews

Comfort Inn & Suites Chestertown Reviews

8.6

Excellent

8.8

Cleanliness

8.6

Location

8.8

Staff & service

8.6

Property conditions & facilities
Rating 10 - Excellent. 441 out of 870 reviews
Rating 8 - Good. 272 out of 870 reviews
Rating 6 - Okay. 92 out of 870 reviews
Rating 4 - Poor. 42 out of 870 reviews
Rating 2 - Terrible. 23 out of 870 reviews

Reviews

10/10 Excellent

Janelle

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
staff is nice and place is good. proce wise is excellent
Stayed 1 night in Jan 2026

10/10 Excellent

Charles

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Everything was great - the beds and pillows are very comfortable, room very clean and breakfast was decent and staff very friendly.
Stayed 1 night in Oct 2025

10/10 Excellent

Santa

Liked: Cleanliness, amenities, property conditions & facilities
The room was a great size and very clean. The staff were very accommodating and friendly. The amenities were very good. We would definitely recommend this hotel.
Stayed 5 nights in Nov 2025

10/10 Excellent

Ada

Liked: Cleanliness, amenities, property conditions & facilities
Very clean hotel. Perfect if you have to do work at Washington College
Stayed 1 night in Oct 2025

10/10 Excellent

Paula

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This property is clean and welcoming. We were pleasantly surprised. Check in was easy, and the room was great. Breakfast was wonderful! Great place to stay.
Stayed 1 night in Nov 2025

10/10 Excellent

Charlie

Liked: Cleanliness, property conditions & facilities
The lady at the front desk was the best. I did an early check-in, and she was super nice. Thanks, I got one more night with you.
Stayed 1 night in Nov 2025

8/10 Good

Gillian

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Friendly staff, clean room, convenient location.
Stayed 1 night in Aug 2025

8/10 Good

Don

Liked: Cleanliness, staff & service, property conditions & facilities
Breakfast was pretty weak Coffe was good though. Room was clean. Other than breakfast, I would recommend it.
Stayed 2 nights in Oct 2025

10/10 Excellent

Amanda

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Comfortable clean room
Stayed 2 nights in Sep 2025

10/10 Excellent

Federico

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Well received by front desk attendant. Room clean!
Stayed 2 nights in Sep 2025

10/10 Excellent

Anne

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Comfortable room, friendly staff.
Stayed 2 nights in May 2025

8/10 Good

Christine

Liked: Cleanliness, property conditions & facilities
It was a clean comfortable spot to rest for the night.
Stayed 1 night in Jul 2025

8/10 Good

Barbara

It was just fine. Very clean and efficient. Just not in a super exciting spot
Stayed 2 nights in Sep 2025

10/10 Excellent

Verified traveler

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Service was great all the staff we came in contact with were kind and helpful from showing us how to work the TV to giving us bottled water when the drink vending machine was out. We enjoyed our stay and the location was very close to Chestertown and Rock Hall.
Stayed 2 nights in Jul 2025

8/10 Good

Mark

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Room was clean. Carpet seemed fairly new. Tub/shower could us an upgrade. Toilet only flushed by holding down the handle until completely empty. Could not adjust the AC unit. Overall it was a great place and felt safe.
Stayed 2 nights in Oct 2025

10/10 Excellent

Anita

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great stay. Sorry pool was closed
Stayed 2 nights in May 2025

6/10 Okay

Jeremy

Is an okay place. Relatively clean, people are nice. Coffee at breakfast is the worse I have ever tasted, anywhere ever.
Stayed 3 nights in Jul 2025

10/10 Excellent

Dianna

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Very clean comfortable room, friendly staff, nice breakfast. Would definitely stay again!
Stayed 2 nights in Oct 2024

10/10 Excellent

William

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Staff was efficient and very helpful. Clean room with microwave & fridge - well stocked linens in bathroom - great breakfast - thank you for a comfortable stay.
Stayed 1 night in Apr 2025

10/10 Excellent

Brenda L.

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Our stay was very quiet and relaxing.
Stayed 1 night in Feb 2024

10/10 Excellent

Lewis

clean and comfy
Stayed 1 night in Mar 2025

10/10 Excellent

Mary

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Check-in was quick & easy. The gentleman at the desk was wonderfully pleasant and very welcoming. Our room was clean and spacious. Beds were clean and comfortable.
Stayed 1 night in Apr 2025

10/10 Excellent

Veronica

Liked: Cleanliness, amenities, property conditions & facilities
We have stayed with this Comfort Inn, Chestertown, MD location in the past. Breakfast is handy, nearby grocery store and eateries are convenient. Farmers Market on Saturday and trendy Mom & Pop shops are close by. The staff are efficient and ice machines are abundant along with a washer/dryer (coins required) are an appreciated touch not to mention plenty of hot water for the shower. Best of all the pool has been scrubbed sparkling clean up and running beautifully...that was a real happy surprise.
Stayed 2 nights in Jul 2025

10/10 Excellent

Connie

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

Excellent stay in Chestertown Maryland

After a slight glitch with my reservation which was EXPERTLY RESOLVED BY the front desk professional Tracie Patrick, my stay was excellent. The room was clean, large, well appointed. The bed was comfortable. The temperature control was very efficient. The room had mini refrigerator, coffee service and microwave. The water in the sink and the shower became comfortably hot. Plenty of free parking. They offer free breakfast, but I did not partake. I think the room was a bit pricey, but it was Labor Day weekend so I suppose that explains it. I would readily stay here again.
Stayed 1 night in Aug 2025

10/10 Excellent

Deborah

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Friendly atmosphere and well stocked breakfast bar! Comfortable clean room!
Stayed 1 night in Jan 2025