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. Mac: Safari.

Chestertown

Refine search

3 of 11

Price range

 
 
 

Traveller rating

 
 
 

Hotel class

 

Amenity type

 

Hotel brand

Show all brands
Major Brands
Individual Chains
Show only major brands
 

Name contains

Reset
 

Recommended for

 
Free Newsletter

Interested in Chestertown?

We'll send you updates with the latest deals, reviews and articles for Chestertown each week.

Explore the world! TripAdvisor has reviews and information on over 400,000 locations, including:
Vacation Specials
Travel Destinations

Explore other Chestertown resources:

Map of Chestertown Hotels

You are zoomed out too far to see location pins. Please zoom back in.
Search hotels
Search
Your recent searches
  • No recent searches
Map showing X-Y of Z
Clear filter(s)

Chestertown weather essentials

Monthly Averages
Month
High
Low
Dec
43°F 6°C
33°F 0°C
Jan
37°F 2°C
28°F -2°C
Feb
40°F 4°C
31°F 0°C
Mar
46°F 7°C
34°F 1°C
Apr
59°F 15°C
44°F 6°C
May
68°F 20°C
54°F 12°C

Extended Forecast
Friday
25 Dec
Hi:
43°F 6°C
Lo:
40°F 4°C
Saturday
26 Dec
Hi:
49°F 9°C
Lo:
31°F 0°C
Sunday
27 Dec
Hi:
38°F 3°C
Lo:
23°F -5°C
More weather for Chestertown
 | 
Powered by
Weather Underground
Other Destinations
Popular Maryland Destinations
Aberdeen
Annapolis
Baltimore
Cumberland
Easton
Frederick
Ocean City
Saint Michaels

Hotels Travellers Trust

Sort by [ Popularity ] [ Price ]
Comfort Suites 2.5 of 5
160 Scheeler Rd., Chestertown, MD 21620
Comfort Suites
Check Rates ABS:HotelCheckRates-d93725?src=LocalMapsRedesign&fromServlet=LocalMapsRedesign&Action=QC_Button
£93 ($148) Avg. price*
4.5 of 5 stars 50 reviews
#1 of 3 hotels in Chestertown
  • “ Great place to stay! ”
  • We stayed here for a weekend in order to attend an event at the college... more
  • 15 October 2009
Hotel photos | Details
Business Centre Free High-Speed Internet Free Parking Swimming Pool
Holiday Inn Express Hotel & Suites Chestertown 2.5 of 5
150 Scheeler Road, Chestertown, MD 21620
Holiday Inn Express Hotel & Suites Chestertown
Check Rates ABS:HotelCheckRates-d672957?src=LocalMapsRedesign&fromServlet=LocalMapsRedesign&Action=QC_Button
£75 ($120) Avg. price*
4 of 5 stars 8 reviews
#2 of 3 hotels in Chestertown
Hotel photos | Details
Business Centre Fitness Centre Swimming Pool
The Imperial Hotel and Restaurant
208 High Street, Chestertown, MD 21620
The Imperial Hotel and Restaurant
£108 ($172) Avg. price*
3.5 of 5 stars 14 reviews
#3 of 3 hotels in Chestertown