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Holiday Inn Express Hotel & Suites Chestertown
HIExpress.com
USD 114*
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#1 Best Value of 2 hotels in Chestertown
  • Free Wifi
  • Free Parking
  • 2 BED MOBIL ACCESSIBLE ROLL SHWR NOSMK
    USD 114
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  • 2 QUEEN BEDS NONSMOKING
    USD 114
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  • Queen Room with Two Queen Beds - Non-refundable
    USD 114
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  • Room, 2 Queen Beds, Non Smoking - Advance Purchase Offers
    USD 114
    View Deal
  • Queen Room with Two Queen Beds - Non-refundable
    USD 114
    View Deal
  • Room, 2 Queen Beds, Non Smoking - Advance Purchase Offers
    USD 115
    View Deal
  • Room, 2 Queen Beds, Non Smoking - Advance Purchase Offers (Free breakfast, Free WiFi)
    USD 115
    View Deal
  • Room, 2 Queen Beds, Non Smoking - Advance Purchase Offers
    USD 115
    View Deal
  • Room, 2 Queen Beds, Non Smoking - Advance Purchase Offers
    USD 115
    View Deal
  • Room, 2 Queen Beds, Non Smoking - Advance Purchase Offers
    USD 115
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Quality Suites
QualityInn
USD 95*
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#2 Best Value of 2 hotels in Chestertown
  • Free Wifi
  • Free Parking
  • 1 King Bed, Suite, No Smoking
    USD 95
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  • 1 King Bed, Suite, No Smoking
    USD 95
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  • 1 King Bed, Suite, No Smoking, Accessible Room
    USD 100
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  • 1 King Bed, Suite, No Smoking, Accessible Room
    USD 100
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  • 2 Queen Beds, Suite, No Smoking
    USD 105
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  • 2 Queen Beds, Suite, No Smoking
    USD 105
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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
No availability for your dates from these sites
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
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Sleep Inn
SAVE USD 14
USD 124*
Hotels.com
USD 110*
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30.9 km from Chestertown
  • Free Wifi
  • Free Parking
  • Standard Room, 1 Queen Bed, Non Smoking - Advance Purchase Rate (Free breakfast, Free parking, Free
    USD 110
    View Deal
  • Standard Room, 1 Queen Bed, Non Smoking - Advance Purchase Rate
    USD 110
    View Deal
  • Standard Room, 1 Queen Bed, Non Smoking - Advance Purchase Rate
    USD 110
    View Deal
  • Standard Room, 1 Queen Bed, Non Smoking - Advance Purchase Rate
    USD 110
    View Deal
  • Standard Room, 1 Queen Bed, Non Smoking - Advance Purchase Rate
    USD 110
    View Deal
  • Standard Room, 1 Queen Bed, Non Smoking - Advance Purchase Rate
    USD 110
    View Deal
  • Standard Room, 1 Queen Bed, Non Smoking - Advance Purchase Rate
    USD 110
    View Deal
  • 1 Queen Bed, No Smoking
    USD 111
    View Deal
  • Standard Room, 1 King Bed, Non Smoking - Advance Purchase Rate (Free breakfast, Free parking, Free W
    USD 120
    View Deal
  • Standard Room, 1 King Bed, Non Smoking - Advance Purchase Rate
    USD 120
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Holiday Inn Express Kent Island
SAVE USD 11
USD 292*
Booking.com
USD 281*
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31.4 km from Chestertown
  • Free Wifi
  • Free Parking
  • King Room - Non-Smoking - Non-refundable
    USD 281
    View Deal
  • King Room - Non-Smoking - Non-refundable
    USD 281
    View Deal
  • Room, 1 King Bed, Non Smoking - Advance Purchase Offers
    USD 282
    View Deal
  • Room, 1 King Bed, Non Smoking - Advance Purchase Offers
    USD 282
    View Deal
  • Room, 1 King Bed, Non Smoking - Advance Purchase Offers
    USD 282
    View Deal
  • Room, 1 King Bed, Non Smoking - Advance Purchase Offers (Free breakfast, Free WiFi)
    USD 282
    View Deal
  • Room, 2 Queen Beds, Non Smoking - Advance Purchase Offers
    USD 282
    View Deal
  • Room, 2 Queen Beds, Non Smoking - Advance Purchase Offers
    USD 282
    View Deal
  • Room, 2 Queen Beds, Non Smoking - Advance Purchase Offers
    USD 282
    View Deal
  • Room, 2 Queen Beds, Non Smoking - Advance Purchase Offers (Free breakfast, Free WiFi)
    USD 282
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Best Western Kent Narrows Inn
SAVE USD 47
USD 257*
Orbitz.com
USD 210*
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31.6 km from Chestertown
  • Free Wifi
  • Free Parking
  • 0
    USD 209
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  • 1 King Bed
    USD 209
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  • 0
    USD 209
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  • Standard Room, 1 King Bed, Non Smoking, Refrigerator & Microwave
    USD 210
    View Deal
  • Standard Room, 1 Queen Bed, Accessible, Refrigerator & Microwave - Advanced Purchase
    USD 210
    View Deal
  • Standard Room, 1 Queen Bed, Non Smoking, Refrigerator & Microwave
    USD 210
    View Deal
  • Standard Room, 2 Queen Beds, Non Smoking, Refrigerator & Microwave
    USD 210
    View Deal
  • Standard Room, 1 King Bed, Non Smoking, Refrigerator & Microwave
    USD 210
    View Deal
  • Standard Room, 1 Queen Bed, Accessible, Refrigerator & Microwave - Advanced Purchase
    USD 210
    View Deal
  • Standard Room, 1 Queen Bed, Non Smoking, Refrigerator & Microwave
    USD 210
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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 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.