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Best Place to Stay in or Near Chestertown

  • Holiday Inn Express Hotel & Suites Chestertown
  • Quality Suites
  • Tallulah's on Main
  • Mariners Motel
  • Sleep Inn
  • Holiday Inn Express Kent Island
  • Best Western Kent Narrows Inn
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Holiday Inn Express Hotel & Suites Chestertown
Booking.com
US$103
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#1 Best Value of 2 hotels in Chestertown
  • Free Wifi
  • Free Parking
  • Queen Room with Two Queen Beds - Non-refundable
    US$103
    View Deal
  • 2 BED MOBIL ACCESSIBLE ROLL SHWR NOSMK
    US$103
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  • 2 QUEEN BEDS NONSMOKING
    US$103
    View Deal
  • Room, 2 Queen Beds, Non Smoking - Advance Purchase Offers
    US$103
    View Deal
  • Room, 2 Queen Beds, Non Smoking - Advance Purchase Offers
    US$103
    View Deal
  • Room, 2 Queen Beds, Non Smoking - Advance Purchase Offers (Free breakfast, Free WiFi)
    US$103
    View Deal
  • Room, 2 Queen Beds, Non Smoking - Advance Purchase Offers
    US$103
    View Deal
  • Room, 2 Queen Beds, Non Smoking - Advance Purchase Offers
    US$103
    View Deal
  • Room, 2 Queen Beds, Non Smoking - Advance Purchase Offers
    US$103
    View Deal
  • 2 BED MOBIL ACCESSIBLE ROLL SHWR NOSMK
    US$103
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Quality Suites
QualityInn
US$85
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#2 Best Value of 2 hotels in Chestertown
  • Free Wifi
  • Free Parking
  • 1 King Bed, Suite, No Smoking
    US$85
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  • 1 King Bed, Suite, No Smoking
    US$85
    View Deal
  • 1 King Bed, Suite, No Smoking, Accessible Room
    US$90
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  • 1 King Bed, Suite, No Smoking, Accessible Room
    US$90
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  • 2 Queen Beds, Suite, No Smoking
    US$95
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  • 2 Queen Beds, Suite, No Smoking
    US$95
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Still looking for a place to stay?
Chestertown has 11 B&Bs/inns with 1,429 reviews
Brampton Bed and Breakfast Inn
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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$12
US$111
Hotels.com
US$99
View Deal
30.9 km from Chestertown
  • Free Wifi
  • Free Parking
  • Standard Room, 1 Queen Bed, Non Smoking - Advance Purchase Rate (Free breakfast, Free parking, Free
    US$99
    View Deal
  • 1 Queen Bed, No Smoking
    US$99
    View Deal
  • Standard Room, 1 Queen Bed, Non Smoking - Advance Purchase Rate
    US$99
    View Deal
  • Standard Room, 1 Queen Bed, Non Smoking - Advance Purchase Rate
    US$99
    View Deal
  • Standard Room, 1 Queen Bed, Non Smoking - Advance Purchase Rate
    US$99
    View Deal
  • Standard Room, 1 Queen Bed, Non Smoking - Advance Purchase Rate
    US$99
    View Deal
  • Standard Room, 1 Queen Bed, Non Smoking - Advance Purchase Rate
    US$99
    View Deal
  • 1 Queen Bed Nonsmoking
    US$99
    View Deal
  • Standard Room, 1 King Bed, Non Smoking - Advance Purchase Rate (Free breakfast, Free parking, Free W
    US$108
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  • 1 King Bed, No Smoking
    US$108
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Holiday Inn Express Kent Island
Booking.com
US$253
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31.4 km from Chestertown
  • Free Wifi
  • Free Parking
  • King Room - Non-Smoking - Non-refundable
    US$253
    View Deal
  • Room, 1 King Bed, Non Smoking - Advance Purchase Offers
    US$253
    View Deal
  • Room, 1 King Bed, Non Smoking - Advance Purchase Offers
    US$253
    View Deal
  • Room, 1 King Bed, Non Smoking - Advance Purchase Offers
    US$253
    View Deal
  • Room, 1 King Bed, Non Smoking - Advance Purchase Offers (Free breakfast, Free WiFi)
    US$253
    View Deal
  • Room, 2 Queen Beds, Non Smoking - Advance Purchase Offers
    US$253
    View Deal
  • Room, 2 Queen Beds, Non Smoking - Advance Purchase Offers
    US$253
    View Deal
  • Room, 2 Queen Beds, Non Smoking - Advance Purchase Offers
    US$253
    View Deal
  • Room, 2 Queen Beds, Non Smoking - Advance Purchase Offers (Free breakfast, Free WiFi)
    US$253
    View Deal
  • Room, 1 King Bed, Non Smoking - Advance Purchase Offers
    US$253
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Best Western Kent Narrows Inn
SAVE US$23
US$212
Orbitz.com
US$189
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31.6 km from Chestertown
  • Free Wifi
  • Free Parking
  • Standard Room, 1 King Bed, Non Smoking, Refrigerator & Microwave
    US$189
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  • Standard Room, 1 Queen Bed, Accessible, Refrigerator & Microwave - Advanced Purchase
    US$189
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  • Standard Room, 1 Queen Bed, Non Smoking, Refrigerator & Microwave
    US$189
    View Deal
  • Standard Room, 2 Queen Beds, Non Smoking, Refrigerator & Microwave
    US$189
    View Deal
  • 0
    US$189
    View Deal
  • Standard Room, 1 King Bed, Non Smoking, Refrigerator & Microwave
    US$189
    View Deal
  • Standard Room, 1 King Bed, Non Smoking, Refrigerator & Microwave
    US$189
    View Deal
  • Standard Room, 1 King Bed, Non Smoking, Refrigerator & Microwave (Free breakfast, Free WiFi)
    US$189
    View Deal
  • Standard Room, 1 Queen Bed, Accessible, Refrigerator & Microwave - Advanced Purchase
    US$189
    View Deal
  • Standard Room, 1 Queen Bed, Accessible, Refrigerator & Microwave - Advanced Purchase
    US$189
    View Deal
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Mariners Motel
No availability for your dates from these sites
17.7 km from Chestertown
  • Free Wifi
  • Free Parking
Tallulah's on Main
17.0 km from Chestertown
  • Free Wifi
  • Free Parking
*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.