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Holiday Inn Express Hotel & Suites Chestertown
HIExpress.com
$94
View Deal
#1 Best Value of 2 hotels in Chestertown
  • Free Wifi
  • Free Parking
Quality Suites
QualityInn
$71
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#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 1,409 reviews
Great Oak Manor
Booking.com
$239
View Deal
7.9 miles from Chestertown center
  • Free Wifi
  • Free Parking
Brampton Bed and Breakfast Inn
No availability for your dates from these sites
1.5 miles from Chestertown center
  • Free Wifi
  • Free Parking
Simply Bed and Bread
0.3 miles from Chestertown center
  • Free Wifi
  • Free Parking
See all 11 Chestertown B&Bs/inns
See all hotels in or near Chestertown
Sleep Inn
SAVE $10
$96
Booking.com
$86
View Deal
19.2 miles from Chestertown
  • Free Wifi
  • Free Parking
Holiday Inn Express Kent Island
Hotels.com
$144
View Deal
19.5 miles from Chestertown
  • Free Wifi
  • Free Parking
Best Western Kent Narrows Inn
Booking.com
$105
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 Parking
  • Free Internet
*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.