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  • Carla Massoni Gallery203 High St, Chestertown, Maryland
  • Historical Society of Kent County101 Church Aly, Chestertown, Maryland
  • Pam Foss Sculpture Gallery200 High St, Chestertown, Maryland
  • Art on High200 High St, Chestertown, Maryland
  • Emmanuel Chester Parish101 N Cross St, Chestertown, Maryland
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Booking.com
US$100
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#1 Best Value of 13 places to stay in Chestertown
  • Free Wifi
  • Free Parking
Special offer
Savings alert! 10% below average rates

The price you found is 10% lower than this hotel's average rate of US$111/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

SAVE US$4
US$89
QualityInn
US$85
View Deal
#2 Best Value of 13 places to stay in Chestertown
  • Free Wifi
  • Free Parking
Savings alert! 11% below average rates

The price you found is 11% lower than this hotel's average rate of US$95/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

Booking.com
US$59
View Deal
Bed and Breakfast
#3 Best Value of 13 places to stay in Chestertown
  • Free Wifi
  • Free Parking
Official Site
US$355
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Bed and Breakfast
#4 Best Value of 13 places to stay in Chestertown
  • Free Wifi
  • Free Parking
Special offer
Offers & Announcements🍷 Spring Winery Special
Booking.com
US$179
View Deal
Bed and Breakfast
#5 Best Value of 13 places to stay in Chestertown
  • Free Wifi
  • Free Parking
Special offer
Special Price25% off room rate
Travelocity
US$195
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Bed and Breakfast
#6 Best Value of 13 places to stay in Chestertown
  • Free Wifi
  • Free Parking
Other places to stay near Chestertown (24)
Orbitz.com
US$97
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17.7 km from Chestertown
  • Free Wifi
  • Free Parking
SAVE US$4
US$86
Booking.com
US$82
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30.9 km from Chestertown
  • Free Wifi
  • Free Parking
Savings alert! 15% below average rates

The price you found is 15% lower than this hotel's average rate of US$97/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

Booking.com
US$135
View Deal
31.4 km from Chestertown
  • Free Wifi
  • Free Parking
Savings alert! 10% below average rates

The price you found is 10% lower than this hotel's average rate of US$150/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

Booking.com
US$60
View Deal
31.6 km from Chestertown
  • Free Wifi
  • Free Parking
SAVE US$6
US$105
Booking.com
US$99
View Deal
31.6 km from Chestertown
  • Free Wifi
  • Free Parking
Special offer
Special OfferBOOK DIRECT & SAVE
Savings alert! 17% below average rates

The price you found is 17% lower than this hotel's average rate of US$119/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

SAVE US$14
US$173
Booking.com
US$159
View Deal
31.8 km from Chestertown
  • Free Wifi
  • Free Parking
Special offer
SAVE US$11
US$64
Booking.com
US$53
View Deal
32.1 km from Chestertown
  • Free Wifi
  • Free Parking
Savings alert! 25% below average rates

The price you found is 25% lower than this hotel's average rate of US$71/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

Home2.com
US$110
View Deal
32.1 km from Chestertown
  • Free Wifi
  • Free Parking
Special offer
Savings alert! 19% below average rates

The price you found is 19% lower than this hotel's average rate of US$135/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

Expedia.com
US$95
View Deal
32.8 km from Chestertown
  • Free Wifi
  • Free Parking
Special offer
SAVE US$3
US$65
Expedia.com
US$62
View Deal
32.8 km from Chestertown
  • Free Wifi
  • Free Parking
Booking.com
US$67
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32.9 km from Chestertown
  • Free Wifi
  • Free Parking
Booking.com
US$57
View Deal
33.0 km from Chestertown
  • Free Wifi
  • Free Parking
Special offer
Booking.com
US$53
View Deal
33.0 km from Chestertown
  • Free Wifi
  • Free Parking
Booking.com
US$72
View Deal
33.2 km from Chestertown
  • Free Wifi
  • Free Parking
Special offer
Booking.com
US$101
View Deal
33.2 km from Chestertown
  • Free Wifi
  • Free Parking
Special offer
SAVE US$12
US$119
HIExpress.com
US$107
View Deal
33.2 km from Chestertown
  • Free Wifi
  • Free Parking
Special offer
Booking.com
US$76
View Deal
33.2 km from Chestertown
  • Free Wifi
  • Free Parking
Special offer
Savings alert! 11% below average rates

The price you found is 11% lower than this hotel's average rate of US$85/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

Hotels.com
US$109
View Deal
33.3 km from Chestertown
    SAVE US$10
    US$129
    Homewood
    US$119
    View Deal
    33.3 km from Chestertown
    • Free Wifi
    • Free Parking
    Special offer
    Expedia.com
    US$61
    View Deal
    33.3 km from Chestertown
    • Free Wifi
    • Free Parking
    SpringHill Suites
    US$109
    View Deal
    33.3 km from Chestertown
    • Free Wifi
    • Free Parking
    Special offer
    Special OfferMember Rates
    Savings alert! 31% below average rates

    The price you found is 31% lower than this hotel's average rate of US$157/night.

    We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

    ComfortInn
    US$72
    View Deal
    33.3 km from Chestertown
    • Free Wifi
    • Free Parking
    Booking.com
    US$80
    View Deal
    33.4 km from Chestertown
    • Free Wifi
    • Free Parking
    Special offer
    Special OfferSave up to 20%
    Savings alert! 13% below average rates

    The price you found is 13% lower than this hotel's average rate of US$92/night.

    We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

    Booking.com
    US$86
    View Deal
    33.4 km from Chestertown
    • Free Wifi
    • Free Parking
    Special offer
    Savings alert! 18% below average rates

    The price you found is 18% lower than this hotel's average rate of US$105/night.

    We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

    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.
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