Your session will expire in 5 minutes, 0 seconds, due to inactivity. Stay Logged In
Create PIN
All fields are required
If you joined IHG® Rewards Club at a hotel, then you will need to create a 4-digit PIN in order to access your IHG® Rewards Club account.
Unexpected Server Error
Your session has expired. Please sign in to your profile
We are sorry, our system is temporarily unavailable. Please try again later or contact the IHG® Rewards Club Customer Care Center for assistance.
The 4-digit numbers entered must match.
Forgot PIN?
All fields are required
Unexpected Server Error
Your session has expired. Please sign in to your profile
We are sorry, our system is temporarily unavailable. Please try again later or contact the IHG® Rewards Club Customer Care Center for assistance.
Don't have an email address in your profile?

Contact your local IHG® Rewards Club Customer Care to source your PIN and to update your profile with your email address. When you receive your PIN you can also update your email address via www.ihg.com/updateemail.

Chestertown Hotels

Compare Hotels in Chestertown

(e.g. {0})
(e.g. {0})
Processing your request...
Close

Destination
Finding a hotel is easy. Your destination can be:

  • a city (San Francisco)
  • an address (123 Main St., Springfield, IL)
  • an airport (LAX)
  • a point of interest (Fenway Park)
  • Zip Code (30308)

Featured Chestertown Hotels

FROM
CHECK RATES
1
4.5/5

150 Scheeler Rd

Chestertown, MD 21620

United States


Reservations:
1-888-HOLIDAY

Front Desk:
1-410-7780778

FROM
CHECK RATES
2

1020 Kent Narrows Road

Grasonville, MD 21638

United States


Reservations:
1-888-HOLIDAY

Front Desk:
1-410-8274454

FROM
CHECK RATES
3

Holiday Inn Belcamp - Aberdeen Area

City Center, 21.02 mi

4.1/5

1326 Policy Drive

Belcamp, MD 21017

United States


Reservations:
1-888-HOLIDAY

Front Desk:
1-410-2722929

FROM
CHECK RATES
4
4.4/5

4216 Philadelphia Road

Bel Air, MD 21015

United States


Reservations:
1 877 CANDLEWOOD

Front Desk:
1-410-9143060

FROM
CHECK RATES
5

2118 Emmorton Park Road

Edgewood, MD 21040

United States


Reservations:
1-888-HOLIDAY

Front Desk:
1-410-6121200

FROM
CHECK RATES
6
4.5/5

1007 Beards Hill Rd

Aberdeen, MD 21001

United States


Reservations:
1-888-HOLIDAY

Front Desk:
1-410-2728100

FROM
CHECK RATES
7

315 Auto Park Dr

Middletown, DE 19709

United States


Reservations:
1-888-HOLIDAY

Front Desk:

FROM
CHECK RATES
8

Holiday Inn Express & Suites Dover

City Center, 27.53 mi

4.6/5

1780 North Dupont Hwy.

Dover, DE 19901

United States


Reservations:
1-888-HOLIDAY

Front Desk:
1-302-6780600

FROM
CHECK RATES
9

Holiday Inn Dover-Downtown

City Center, 29.18 mi

4.0/5

561 North Dupont Highway

Dover, DE 19901

United States


Reservations:
1-888-HOLIDAY

Front Desk:
1-302-7475050

FROM
CHECK RATES
10
4.4/5

101 Hotel Plaza

North East, MD 21901

United States


Reservations:
1-888-HOLIDAY

Front Desk:
1-410-2870008

FROM
CHECK RATES
11

Holiday Inn Express Easton

City Center, 29.4 mi

4.7/5

8561 Ocean Gateway

Route 50

Easton, MD 21601

United States


Reservations:
1-888-HOLIDAY

Front Desk:
1-410-8196500

FROM
CHECK RATES
12
4.4/5

221 North Gay Street

Baltimore, MD 21202

United States


Reservations:
1-888-HOLIDAY

Front Desk:
1-410-4008045

FROM
CHECK RATES
13
4.6/5

17 Commerce Street

Baltimore, MD 21202

United States


Reservations:
1 877 238 8889

Front Desk:
1-410-6247333

FROM
CHECK RATES
14

Crowne Plaza Annapolis

City Center, 29.83 mi

4.4/5

173 Jennifer Road

Annapolis, MD 21401

United States


Reservations:
1 877 2 CROWNE

Front Desk:
1-410-2663131

FROM
CHECK RATES

101 North Charles Street

Balltimore, MD 21201

United States


Reservations:
1 877 CANDLEWOOD

Front Desk:
1-410-2448181

FROM
CHECK RATES
16
4.3/5

2451 Riva Road

Annapolis, MD 21401

United States


Reservations:
1-888-HOLIDAY

Front Desk:
1-410-2244317

FROM
CHECK RATES
17

Kimpton Hotel Monaco Baltimore

City Center, 29.92 mi


2 N. Charles Street

Baltimore, MD 21201

United States


Reservations:
1 800 KIMPTON

Front Desk:
1-443-6926170

FROM
CHECK RATES

105 West Fayette Street

Baltimore, MD 21201

United States


Reservations:
1 877 2 CROWNE

Front Desk:
1-410-3475707

Whether it's your first visit or Chestertown is a favorite travel destination, get ready to explore all that Chestertown has to offer and find the perfect temporary home base with help from IHG. Our easy-to-navigate website allows you to compare the best hotels in Chestertown by reading through our honest 7488 reviews from verified hotel guests. When you book your room with IHG, you're assured a great deal and lowest rate with our Best Price Guarantee. We boast 18 hotels in Chestertown, MD, all with a distinctive flair and a variety of amenities, and you can conveniently narrow down your choices and book your room directly with us.

No matter if you're travelling to Chestertown to attend a conference, unwind on vacation, or enjoy a romantic weekend getaway, we have you covered. And if your travels take you to another part of the world, you'll find an IHG accommodation that meets your needs. From hotels in the heart of it all to luxury accommodations off the beaten path, IHG offers great hotel deals in Chestertown and throughout the world.

Enter your travel dates to view the best offers on hotel rooms, and use our advanced search features to find the hotels with the amenities you desire. When you stay as an IHG Rewards Club member, you also enjoy free in-hotel Internet access. Some of our hotels boast indoor swimming pools, while others offer hot breakfast, in-room kitchens, and spa services. We make it easy to book the perfect hotel for your trip.

Latest Chestertown Hotel Reviews


Great service
By buckles55
I have stayed at this Hotel several times now and the service has always been excellent with friendly staff. [Less]
First time
By Summer 2018
I would recommend hotel stay.Continental breakfast very nice, not just bagels and coffee. Slept very well altho I was on 2nd floor and heard movement above my floor. That was a downer they were [More] heavy footers. [Less]
Good Clean Property
By Dick
Convenient place to stay in upper Kent County. Good breakfas t b ar. [Less]
Very welcoming
By supermom4
All staff during the entire stay were all very welcoming and accommodating. Hotel property and rooms were very clean. Would definitely stay here again. [Less]
Very Pleased
By Satisfied
As indicated per question answers, we found this hotel to be very clean, near attractions and restaurants, with a pleasant and responsive staff. [Less]
Great stay
By Terry
Excellent accommodations, price and convenience. ................................................ [Less]
Beautiful
By Jojo
Great location - beautiful view from our room - loved the doc - could walk to many restaurants and was able to see a band [Less]
Beautiful view, waterfront setting and close to a variety of restaurants.
By Cherie
Came for a Birthday getaway overnight celebration and was very pleased with everything. Had a great time, the hotel was clean and pretty and the front desk staff very welcoming and friendly. [Less]
Kent Narrows
By Bobby
We love the location for us. Close walk to may great restaurants and nightlife Staff is always nice and is a good value We can walk to out marina too [Less]

Explore Destinations by Interest

Close
Select Check-In Date
Select Check-Out Date
Check Availability on RegentHotels.com

Visit our groups and meetings page  Link will open in new browser window. to find the perfect hotel for your upcoming meeting, event or group of 10 or more rooms. Ready to book 10 or more rooms now? Call 1-800-MEETING (Outside the US? Click here).  Link will open in new browser window.