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Quality Suites
SAVE US$3
US$93
QualityInn
US$90
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#1 Best Value of 2 hotels in Chestertown
  • Free Wifi
  • Free Parking
Holiday Inn Express Hotel & Suites Chestertown
SAVE US$98
US$203
HIExpress.com
US$105
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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 1,387 reviews
Brampton Bed and Breakfast Inn
Official Site
US$265
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2.4 km from Chestertown centre
  • Free Wifi
  • Free Parking
Great Oak Manor
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12.8 km from Chestertown centre
  • Free Wifi
  • Free Parking
Simply Bed and Bread
0.5 km from Chestertown centre
  • Free Wifi
  • Free Parking
See all 11 Chestertown B&Bs/inns
See all hotels in or near Chestertown
Sleep Inn
SAVE US$13
US$114
SleepInn
US$101
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30.9 km from Chestertown
  • Free Wifi
  • Free Parking
Holiday Inn Express Kent Island
SAVE US$187
US$365
TripAdvisor
US$178
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31.4 km from Chestertown
  • Free Wifi
  • Free Parking
Best Western Kent Narrows Inn
SAVE US$55
US$196
Booking.com
US$141
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31.6 km from Chestertown
  • Free Wifi
  • Free Parking
Mariners Motel
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17.7 km from Chestertown
  • Free Wifi
  • Free Parking
Tallulah's on Main
17.0 km from Chestertown
  • Free Parking
  • Free Internet
*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.