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

  • Sort by:
  • Traveler 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
Top Deal
$132*
$97* /night
View Deal
Expedia.com
$97*
Booking.com
$97*
HotelQuickly
$132*
#2 of 2 Hotels in Chestertown by Best Value + Top Rated
Top Deal
$100*
$95* /night
View Deal
Priceline
$100*
TripAdvisor
$95*
Expedia.com
Still looking for a place to stay?
Chestertown has 11 B&Bs/inns with 1,374 reviews
0.3 miles from Chestertown center
#3 of 11 Chestertown B&B and Inns
1.5 miles from Chestertown center
#1 of 11 Chestertown B&B and Inns
Loading prices...
TripAdvisor
Booking.com
Priceline
7.9 miles from Chestertown center
#2 of 11 Chestertown B&B and Inns
No availability for your dates from these sites
Booking.com
Travelocity
Hotwire.com
See all 11 Chestertown B&Bs/inns
See all hotels in or near Chestertown
11.0 miles from Chestertown
$90* /night
View Deal
Orbitz.com
$90*
Travelocity
$90*
TripAdvisor
$90*
Top Deal
$102*
$90* /night
View Deal
Orbitz.com
$90*
SleepInn
$90*
getaroom.com
$102*
Top Deal
$166*
$131* /night
View Deal
Hotwire.com
$131*
Hotels.com
$131*
HotelQuickly
$166*
19.7 miles from Chestertown
Top Deal
$148*
$100* /night
View Deal
Booking.com
$112*
Expedia.com
$112*
HotelQuickly
$148*
10.6 miles from Chestertown
*Prices are the average nightly price provided by our partners and may not include all taxes and fees. Taxes and fees that are shown are estimates only. 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.