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Comfort Inn & Suites Chestertown

Property class: 2.5

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Photo gallery for Comfort Inn & Suites Chestertown

A modern dining area with a central island, multiple tables, and chairs. There are signs for 'RISP' and 'SILVER' on the wall, and an 'EXIT' sign above a door. - Comfort Inn & Suites Chestertown (Chestertown)
A hotel reception area with a modern design, featuring a reception desk, a seating area, and a hallway leading to other rooms. - Comfort Inn & Suites Chestertown (Chestertown)
A hotel room with two beds, a desk, a TV, and a window with curtains. - Comfort Inn & Suites Chestertown (Chestertown)
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it. - Comfort Inn & Suites Chestertown (Chestertown)
A modern lounge area with seating, a fireplace, and a television. - Comfort Inn & Suites Chestertown (Chestertown)
Located close to Washington College and River Arts Chestertown, Comfort Inn & Suites Chestertown provides free full breakfast, laundry facilities, and a fireplace in the lobby. Free in-room WiFi is available to all guests, along with a gym and a business center.

Reviews

8.6 out of 10
Excellent

Popular amenities

  • Pool
  • Pet friendly
  • Free WiFi
  • Air conditioning

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Skip the crowds, keep the savings. AARP members save more after Labor Day. Book by Oct 7, 2026.

Room options

Available filters for rooms
Showing 11 of 11 rooms

View all photos for 1 King Bed, Nonsmoking

A hotel room with a large bed, bedside lamps, a desk, a TV, and a window with curtains.

1 King Bed, Nonsmoking

  • Sleeps 2
  • 1 King Bed

View all photos for 1 King Bed, Nonsmoking, Accessible

A hotel room with a large bed, a desk, a chair, a lamp, and a window with curtains.

1 King Bed, Nonsmoking, Accessible

  • Sleeps 2
  • 1 King Bed

View all photos for 1 King Bed, Suite, Nonsmoking

A hotel room with a large bed, bedside lamps, a desk, a TV, and a window with curtains.

1 King Bed, Suite, Nonsmoking

  • Sleeps 2
  • 1 King Bed

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

A hotel room with a large bed, two bedside lamps, a chair, a nightstand, and a window with curtains.

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

8.8 out of 10
Excellent
(5 reviews)
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed

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

A hotel room with two beds, a large window with curtains, and a wall-mounted heater.

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

8.8 out of 10
Excellent
(3 reviews)
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds

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

A hotel room with two beds, a large window with curtains, and a wall-mounted heater.

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

10.0 out of 10
Exceptional
(1 review)
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds

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

A hotel room with a large bed, two bedside lamps, a chair, a nightstand, and a window with curtains.

Standard Room, 1 King Bed, Non Smoking

8.4 out of 10
Very good
(18 reviews)
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed

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

A hotel room with two beds, a large window with curtains, and a wall-mounted heater.

Standard Room, 2 Queen Beds, Non Smoking

8.8 out of 10
Excellent
(53 reviews)
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds

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

A hotel room with two beds, a desk, and a kitchenette.

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

10.0 out of 10
Exceptional
(1 review)
  • 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

A hotel room with a large bed, a chair, a nightstand, and a dresser.

Suite, 1 King Bed with Sofa bed, Non Smoking

7.6 out of 10
Good
(7 reviews)
  • 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 two beds, a desk, and a kitchenette.

Suite, Multiple Beds, Non Smoking

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

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
150 Scheeler Road, Chestertown, MD, 21620

What's nearby

  • A field of soybeans with a barn and silos in the background.
    Washington College
    8 min walk - 0.4 miles
  • Rolling Road Park
    16 min walk - 0.9 miles
  • Larrabee Arts Center
    18 min walk - 1.0 mile
  • Chestertown Dog Park
    2 min drive - 0.9 miles
  • Chestertown Farmers Market
    2 min drive - 1.7 miles

Getting around

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

Restaurants

  • McDonald's
    11 min walk
  • Royal Farms
    5 min drive
  • Dunkin
    5 min walk
  • Procolino's
    10 min walk
  • Royal Farms
    2 min drive

Similar properties

Exterior
Red Roof Inn & Suites Chestertown
Chestertown
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
7.2 out of 10, 491, 491 reviews
Red Roof Inn & Suites Chestertown
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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 on-site 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 pet, 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 pet, 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 fire extinguisher, 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)

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.

Is Comfort Inn & Suites Chestertown pet-friendly?

Yes, pets are allowed at this property. There's a fee of USD 25 per pet, 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).

Can I cancel my reservation for free and receive a full refund?

Yes, this property offers free cancellation on select room rates, because flexibility matters! Please refer to the property cancellation policy on our site for more details about any exclusions or requirements.

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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. 501 out of 978 reviews
Rating 8 - Good. 295 out of 978 reviews
Rating 6 - Okay. 104 out of 978 reviews
Rating 4 - Poor. 50 out of 978 reviews
Rating 2 - Terrible. 28 out of 978 reviews

Reviews

Verified review

10/10 Excellent

Amy

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This was a very well maintained place and the breakfast was really good.
Stayed 1 night in Aug 2026
Verified review

10/10 Excellent

Deanna

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Clean and affordable amenities and a decent breakfast!
Stayed 1 night in Jul 2026
Verified review

10/10 Excellent

Anna

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The entire hotel smelled so fresh and clean…beds very comfortable and our room was spotless. Would recommend and stay there again
Stayed 1 night in Aug 2026
Verified review

10/10 Excellent

Brandon

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Our room was clean, staff was friendly and a fair amount to choose from for breakfast. Would absolutely stay here again
Stayed 2 nights in Jul 2026
Verified review

4/10 Poor

Anna

Liked: Cleanliness, amenities
Disliked: Staff & service
Nice breakfast! However they had a planned hot water outage and never informed the guests. If I had known that we would have stayed somewhere else. We missed church because of that.Otherwise the hotel met all of our needs. The lady who made the breakfast was very sweet and so was housekeeping.
Stayed 2 nights in Aug 2026
Verified review

10/10 Excellent

E Gaill

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Our receptionist was very friendly and helpful. The room was clean and modern. Cooling system was good. Nice bathroom. The outdoor pool was clean and quiet and well maintained. Breakfast was standard travel fare but it was very fresh.
Stayed 1 night in Aug 2026
Verified review

10/10 Excellent

Jennifer

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The hotel was beautifully maintained. The rooms were clean and updated. Very good location!
Stayed 1 night in May 2026
Verified review

10/10 Excellent

Rebecca

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Room was clean, comfortable & spacious. Good value for cost. Good breakfast. Vending only on first floor w/no diet sodas offered.
Stayed 1 night in Jul 2026
Verified review

10/10 Excellent

Robert

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Clean rooms, environment and best place to stay.
Stayed 4 nights in Mar 2026
Verified review

6/10 Okay

Sara

Liked: Staff & service
Disliked: Amenities, property conditions & facilities
Room was clean. Breakfast space and options were good. Trash can full of dog poop? out back was overflowing and unsightly. Pool area looked like either there was a storm or wild party. Furniture and towels thrown inside pool, which looked like it hadn’t been cleaned in a while. Patio furniture tossed and turned over. So, we didn’t use the pool.
Stayed 1 night in Aug 2026
Verified review

10/10 Excellent

Robert

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Staying is peaceful and the rooms clean.
Stayed 3 nights in Mar 2026
Verified review

10/10 Excellent

Ruth Ann

Liked: Cleanliness
Clean and courteous staff.
Stayed 1 night in Mar 2026
Verified review

8/10 Good

Caroline

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Comfortable beds. Breakfast was decent, with hot and cold options. Shower did not have pressure. Pool was small but nice. Unfortunately we were there Wednesday -Sunday and never were given new towels or a room cleaning. And the last morning we found ants in the room.
Stayed 1 night in Jun 2026
Verified review

10/10 Excellent

ROMMEL HOSMIN

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Clean room, friendly staff, shops nearby Everything was good
Stayed 1 night in Mar 2026
Verified review

10/10 Excellent

Ruth Ann

Liked: Cleanliness
Nice clean facility for the money and staff very cordial
Stayed 1 night in Mar 2026
Verified review

10/10 Excellent

Ruth Ann

Liked: Cleanliness
Clean and helpful
Stayed 3 nights in Mar 2026
Verified review

10/10 Excellent

Robert

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Room was clean and ready for use. Staff was friendly.
Stayed 1 night in Mar 2026
Verified review

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
Verified review

10/10 Excellent

Matthew

Liked: Cleanliness, staff & service, property conditions & facilities
Frindly staff. Slight noise but not bad. Rooms clean and comfortable.
Stayed 1 night in Mar 2026
Verified review

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
Verified review

8/10 Good

Gillian

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

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
Verified review

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
Verified review

10/10 Excellent

jason

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Good location. Very pricey but not much competition
Stayed 2 nights in Nov 2025
Verified review

10/10 Excellent

Anne

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