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Quality Suites
SAVE USD 3
USD 93*
QualityInn
USD 90*
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#1 Best Value of 2 hotels in Chestertown
  • Free Wifi
  • Free Parking
Holiday Inn Express Hotel & Suites Chestertown
SAVE USD 5
USD 110*
HIExpress.com
USD 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 1,391 reviews
Brampton Bed and Breakfast Inn
Official Site
USD 287*
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2.4 km from Chestertown centre
  • Free Wifi
  • Free Parking
Great Oak Manor
SAVE USD 41
USD 315*
Orbitz.com
USD 274*
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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 USD 13
USD 114*
Booking.com
USD 101*
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30.9 km from Chestertown
  • Free Wifi
  • Free Parking
Holiday Inn Express Kent Island
SAVE USD 21
USD 157*
Booking.com
USD 136*
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31.4 km from Chestertown
  • Free Wifi
  • Free Parking
Best Western Kent Narrows Inn
SAVE USD 48
USD 170*
Booking.com
USD 122*
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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.