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.
The latest reviews. The lowest prices. The perfect place to shop for hotels.

Chestertown Hotels

View map
  • Sort by:
  • Traveller Ranked
  • Lowest Price
  • Distance
TripAdvisor members only.
Login for exclusive access to hotel deals up to 40% off
Login to get best prices
#1 of 2 Hotels in Chestertown by Best Value + Top Rated
US$ 108* /night
View Deal
TripAdvisor
US$ 108*
Hotels.com
US$ 108*
HIExpress.com
US$ 108*
View all 10 deals 
#2 of 2 Hotels in Chestertown by Best Value + Top Rated
Top Deal
US$ 111*
US$ 105* /night
View Deal
TripAdvisor
US$ 105*
Priceline
US$ 111*
Hotels.com
View all 8 deals 
Still looking for a place to stay?
Chestertown has 11 Guest Houses with 1,371 reviews
2.4 km from Chestertown centre
#1 of 11 Chestertown B&B and Inns
Loading prices...
TripAdvisor
Booking.com
Expedia.com
View all 9 deals 
12.8 km from Chestertown centre
#2 of 11 Chestertown B&B and Inns
No availability for your dates from these sites
Booking.com
Expedia.com
Travelocity
View all 8 deals 
0.5 km from Chestertown centre
#3 of 11 Chestertown B&B and Inns
See all 11 Chestertown Guest Houses
See all hotels in or near Chestertown
17.7 km from Chestertown
US$ 100* /night
View Deal
TripAdvisor
US$ 100*
Hotels.com
US$ 100*
Hotwire.com
US$ 100*
View all 7 deals 
Top Deal
US$ 114*
US$ 100* /night
View Deal
TripAdvisor
US$ 100*
Hotels.com
US$ 100*
getaroom.com
US$ 114*
View all 11 deals 
Top Deal
US$ 183*
US$ 131* /night
View Deal
TripAdvisor
US$ 131*
Orbitz.com
US$ 146*
HotelQuickly
US$ 183*
View all 10 deals 
31.6 km from Chestertown
Top Deal
US$ 163*
US$ 124* /night
View Deal
TripAdvisor
US$ 124*
Booking.com
US$ 124*
HotelQuickly
US$ 163*
View all 13 deals 
17.0 km from Chestertown
*Prices are provided by our partners, and reflect average nightly room rates, including taxes and fees that are fixed, known to our partners, and due at time of booking. Please see our partners for more details.
Chestertown Travel Forum Need specific advice visiting Chestertown, Maryland? Visit the TripAdvisor Travel Forum for Chestertown and ask our Destination Experts and the travel community.