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.
View map
Sponsored by:
Clear all
Your Selections
  Free Wifi Budget Breakfast included Pool Mid-range Free Parking Suites Fitness centre Business Business Centre & up & up & up Non-Smoking Hotel Meeting Rooms Internet £ ££ £££ ££££ Family-friendly Nature Lover Quiet Pets Allowed Foodie Accessible rooms Quality Inn Holiday Inn Express Within 25 mi
Price per night
Enter dates & see best prices
to
Amenities
More
Amenities
Location
Any Distance
from
Traveller Rating
Hotel class
Style
More
Style
Hotel brand
  • Sort by:
  • Traveller Ranked
  • Best Value
  • Lowest Price
  • Distance
TripAdvisor members only.
Login for exclusive access to hotel deals up to 40% off
Login to get best prices
Holiday Inn Express Hotel & Suites Chestertown
HIExpress.com
US$114
View Deal
#1 Best Value of 2 hotels in Chestertown
  • Free Wifi
  • Free Parking
Quality Suites
QualityInn
US$95
View Deal
#2 Best Value of 2 hotels in Chestertown
  • Free Wifi
  • Free Parking
Still looking for a place to stay?
Chestertown has 11 B&Bs/inns with 1,429 reviews
Brampton Bed and Breakfast Inn
No availability for your dates from these sites
1.5 miles from Chestertown centre
  • Free Wifi
  • Free Parking
Great Oak Manor
No availability for your dates from these sites
7.9 miles from Chestertown centre
  • Free Wifi
  • Free Parking
Simply Bed and Bread
0.3 miles from Chestertown centre
  • Free Wifi
  • Free Parking
See all 11 Chestertown B&Bs/inns
See all hotels in or near Chestertown
Sleep Inn
SleepInn
US$111
View Deal
19.2 miles from Chestertown
  • Free Wifi
  • Free Parking
Holiday Inn Express Kent Island
SAVE US$14
US$282
Booking.com
US$268
View Deal
19.5 miles from Chestertown
  • Free Wifi
  • Free Parking
Best Western Kent Narrows Inn
Orbitz.com
US$210
View Deal
19.7 miles from Chestertown
  • Free Wifi
  • Free Parking
Mariners Motel
No availability for your dates from these sites
11.0 miles from Chestertown
  • Free Wifi
  • Free Parking
Tallulah's on Main
10.6 miles from Chestertown
  • Free Wifi
  • Free Parking
*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. Other miscellaneous taxes and hotel fees which are not fixed or due at time of booking may be payable at the property at time of stay. Please see our partners for more details.