We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
New! Find and book your ideal hotel on TripAdvisor — and get the lowest prices

Holiday Inn Express Hotel & Suites Chestertown

Show Prices
Certificate of Excellence
Book on TripAdvisor
Trusted partner. We work with to make your booking as easy as possible.
Secure payments. We use industry-leading practices to keep your information secure.
Enter dates for best prices
powered by PriceFinder
1 room
Check In Check Out
Please enter your travel dates to continue
Check Availability
Compare best prices from top travel sites
and 4 more sites!
Professional photos
Holiday Inn Express Hotel & Suites Chestertown
View Map
{"widget":{"name":"ibex_photo_carousel","template":"ibex_photo_carousel__widget","dust":{"nav_controls":"ibex_photo_carousel__nav_controls"},"divClasses":"prw_rup prw_ibex_photo_carousel","moduleList":["handlers"],"js":{"handlers":"(ta.prwidgets.getjs(this,'handlers'))"}},"scriptFlags":null,"containerClass":null}
Add Photo Write a Review

135 Reviews from our TripAdvisor Community

Traveller rating
Traveller type
Time of year
Language
There are newer reviews for Holiday Inn Express Hotel & Suites Chestertown
See the most recent reviews
Showing 135: English reviews
Wellesley Island
Reviewed 6 June 2016

We shared a room with two queens and a climate control system that was persnickety. Room was adequate. There is a gym and a pool but we did not explore. Humidity was a problem in the elevator. Breakfast room was spacious and updated. Good selection of breakfast offerings included with lodging.

 Report
Helpful?
Thank lettrix
IHGService, Guest Relations Manager at Holiday Inn Express Hotel & Suites Chestertown, responded to this review

Dear lettrix, Thank you for your feedback regarding your stay at Holiday Inn Express Hotel & Suites Chestertown, MD. We take our guest comments very seriously and always strive to provide comfortable and friendly accommodations. We appreciate your nice comment about the room and breakfast. However, we’re sorry we fell below your expectation regarding the elevator. We will address this...

Wells, Maine
Reviewed 30 May 2016

We were looking for a hotel in the Dover, Delaware area in mid-May on short notice and were having little success due to a big racing event at the Dover raceway. Everything in Dover was booked solid or was costing over $250/night. After searching towns close to Dover, finally found a room available at the Holiday Inn Express in Chestertown,...

 Report
Helpful?
Thank kedavis4
SaraHIEX, Manager at Holiday Inn Express Hotel & Suites Chestertown, responded to this review

Thank you for your wonderful review. We are happy to hear that you enjoyed your stay with us. We hope you will visit us again soon.

Arlington, Virginia
Reviewed 24 May 2016

We asked for a quite area of the hotel and we were very happy to be given a suite on the third floor at the end of the hall away from any noise. Managers were very accommodating and offered advice about places to eat and things to see. The hotel is kept very clean and is one that offers to...

 Report
Helpful?
Thank Brotherdickdca1981
SaraHIEX, Manager at Holiday Inn Express Hotel & Suites Chestertown, responded to this review

Thank you very much for your great review. We are so happy to hear that you enjoyed your stay with us and that our staff was able to accommodate your requests. We hope you will visit us again, the next time you are in the area!

Tampa, Florida
Reviewed 21 May 2016 via mobile

Lodged here this week on a business trip. This is an upgraded Holiday Inn Express. Lovely landscaping and less than a mile from historic downtown. Personnel very hospitable. My room was very clean and well appointed. I would highly recommend a stay.

 Report
Helpful?
Thank Stephanie C
SaraHIEX, Manager at Holiday Inn Express Hotel & Suites Chestertown, responded to this review

Thank you for your fabulous review. I am super excited to hear that you enjoyed your stay with us. Come visit us again soon!

Alexandria, Virginia
Reviewed 11 May 2016

For a short stay in Chesterton, would recommend. Staff especially courteous and helpful with local places to visit. Breakfast offers need improvement, too few choices. Parking free, and extensive. Room was large and comfortable.

 Report
Helpful?
Thank Christine G
Reviewed 26 April 2016

Stayed one night. Nice hotel. Very clean. We had our dog with us and this hotel is very pet friendly. The breakfast in the morning was very nice. I loved the coffee. We would stay here again if we were in the area.

 Report
Helpful?
Thank Stephanie S
Monroe, Tennessee
Reviewed 23 March 2016 via mobile

Very clean, affordable and in a very quiet area, definitely would stay there again....beds were updated and comfy! Staff was kind and helpful and breakfast was better than your typical continental and very good coffee! Only stayed one night but for a weary traveler it was exactly what we needed.

 Report
Helpful?
Thank jleannditto
Reviewed 13 March 2016 via mobile

A bit far from 301 and route 50 still a charming town with nice little hotel Room is big I had 1st floor I got in late but no troubles Location across from shopping plaza but down side road very convient

 Report
Helpful?
Thank Boatfriend
IHGService, Guest Relations Manager at Holiday Inn Express Hotel & Suites Chestertown, responded to this review

Dear Boatfriend, Thank you for taking the time to post a candid review. We are elated by the fact that you were able to commend our location close to the shopping plaza and highway and found our beds to be big. We hope that you get the opportunity to visit us again so that we can serve you once more....

Elkins, West Virginia
Reviewed 8 February 2016

We stayed in a first floor room by request and were situated close to the back door and the pool. Initially I was concerned the pool smell would spread into our room. It did not; nor was the proximity to the rear door a noise factor. My only concern was their lack of forgotten amenities, specifically shower caps and Emory...

 Report
Helpful?
Thank Juanita S
Washington DC, District of Columbia
Reviewed 24 November 2015

The HIE in Chestertown proved to be an excellent choice for an overnight trip we planned to see the legendary Chesapeake winter waterfowl. The oldtown section of Chestertown is lovely, with lots of shops and restaurants and even a park on the Chester River. The HIE is located a couple miles away from that charming oldtown, but it was a...

 Report
Helpful?
Thank Michael B

29 photos of this hotel

Traveller photos: See what travellers like you saw

Viewed
All Traveller Photos (5)
Viewed
Room/Suite (4)
Viewed
Other (1)

Management photos: Courtesy of the property manager

Viewed
All Management Photos (24)
Viewed
Hotel & Grounds (3)
Viewed
Room/Suite (10)
Viewed
Dining (5)
Viewed
Pool/Beach Area (2)
Viewed
Business Centre/Function Rooms (1)
Viewed
Other (3)
Check In Check Out
Hotels you might also like...
Also consider these accommodations in or near Chestertown
0.1 km away
Quality Suites
Quality Suites
#2 of 2 in Chestertown
108 reviews
32.2 km away
Holiday Inn Express Kent Island
32.6 km away
Hilton Garden Inn Kent Island
Show Prices
Show Prices
Show Prices
32.4 km away
BEST WESTERN Kent Narrows Inn
18.1 km away
Inn at Haven Harbour
Inn at Haven Harbour
#1 of 3 in Rock Hall
89 reviews
2.8 km away
Brampton Bed and Breakfast Inn
Show Prices
Show Prices
Show Prices

Amenities

Highlights
  • Free High Speed Internet ( WiFi )
  • Free Parking
  • Pool
  • Fitness Centre with Gym / Workout Room
  • Free Breakfast
  • Restaurant
About the property
  • Wheelchair Access
  • Non-Smoking Hotel
  • Pets Allowed ( Dog / Pet Friendly )
Things to do
  • Pool
  • Fitness Centre with Gym / Workout Room
  • Restaurant
Room types
  • Suites
  • Family Rooms
  • Kitchenette
  • Non-Smoking Rooms
Internet
  • Free Internet
  • Free High Speed Internet ( WiFi )
Services
  • Free Parking
  • Business Centre with Internet Access
  • Free Breakfast
  • Meeting Rooms
  • Self-Serve Laundry
Official Description (provided by the hotel)
Welcome to the Holiday Inn Express Hotel in Chestertown, Maryland near Washington College. Our new Chestertown hotel near Washington College provides comfortable hotel rooms in Chestertown, Maryland. Our Chestertown hotel is located near several Chestertown attractions including the Hopkins Game Farm, Goose Valley Farms, Crimson Staples, Crumpton Auctions and the Waterman's Museum. Guests can further enjoy their Chestertown vacation by taking advantage of the one-of-a-kind shopping experience historical downtown Chestertown offers. Downtown Chestertown, just minutes from our hotel, houses several locally owned and operated stores. Conveniently located near the Chester River, guests of our hotel in Chestertown, Maryland, can enjoy Maryland's picturesque New England scenery while paddling or riding down the Chester River. Visitors can also take walking tours of historical Chestertown, MD, discover Chestertown's rich maritime history or take daytime or sunset sailing tours. Unlike other Chestertown hotels, the Holiday Inn Express Hotel in Chestertown, Maryland, offers comfortable rooms and is conveniently located near Washington College. During your Chestertown visit, enjoy our hotel's signature hot breakfast bar along with other amenities such as high-speed, wireless Internet access and an indoor pool. Make your reservations at our Chestertown, MD, hotel today and enjoy our excellent hotel rates. ... more   less 

Additional Information about Holiday Inn Express Hotel & Suites Chestertown

Address: 150 Scheeler Rd, Chestertown, MD 21620-1031
Region: United States > Maryland > Chestertown
Price Range: $120 - $201 (Based on Average Rates for a Standard Room)
Hotel Class:2.5 star — Holiday Inn Express Hotel & Suites Chestertown 2.5*
Number of rooms: 81
Reservation Options:
TripAdvisor is proud to partner with Hotels.com, IHG, Booking.com, Expedia, Odigeo, Travelocity and Priceline so you can book your Holiday Inn Express Hotel & Suites Chestertown reservations with confidence. We help millions of travellers each month to find the perfect hotel for both holiday and business trips, always with the best discounts and special offers.
Also Known As:
Holiday Inn Express Hotel And Suites Chestertown
Holiday Inn Chestertown
Chestertown Holiday Inn
Is This Your TripAdvisor Listing?
Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more.
Claim Your Listing

Questions & Answers

Here's what travellers have asked, with answers from Holiday Inn Express Hotel & Suites Chestertown staff and other travellers.
2 questions
Ask a question
Brick, New Jersey
1 month ago

See all questions (2)

Questions? Get answers from Holiday Inn Express Hotel & Suites Chestertown staff and past guests.
Posting guidelines
Typical questions asked:
  • Can tickets for local attractions be purchased at the front desk?
  • Do you have to pay extra for a mini-fridge?
  • At what time does the pool open each day?

See which rooms travellers prefer

“We've never had a "bad" room.”
 of 5 bubbles 704michaela, 27 Nov 2016 | Read review
“avoid room 216”
 of 5 bubbles E7639CMjenc, 1 Nov 2016 | Read review
“We stay in upper floors away from elevators and ice machines for quieter stay.”
 of 5 bubbles admiralm2015, 28 Sep 2016 | Read review
“Room discount for Crumpton auction attendees.”
 of 5 bubbles FranF762, 28 Sep 2016 | Read review
“They had an elevator.”
 of 5 bubbles SurfingTurkIslands, 27 Jun 2016 | Read review
5 of 5
Enter dates for best prices
Check In Check Out
Price Your Stay