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Chestertown Cottages

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Featured Cottages in Chestertown

Estimated price for 1 night/2 adults

Waterfront 3 Br/1 ba Country Cottage w/ Gameroomdeep Water,dock, 2 mi From Town
Waterfront 3 Br/1 ba Country Cottage w/ Gameroomdeep Water,dock, 2 mi From Town
Chestertown, MD
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4.7/5 (7 reviews)

We had a great time. The house was very clean and comfortable. The grandkids had a lot of room inside and out. Already want to return. Thank you for a great vacation spot.

Reviewed on Aug 7, 2018
Located in Chestertown, this family-friendly cottage is 2.3 mi (3.6 km) from Washington College, and within 16 mi (25 km) of The Mainstay and Tilmon's Island ...
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Estimated price for 1 night/2 adults

Holiday Inn Express Hotel & Suites Chestertown

Holiday Inn Express Hotel & Suites Chestertown

150 Scheeler Road, Chestertown, MD
    2.5 out of 5.0
     
     
    4.3 out of 5 (327 reviews)

    Holiday Inn Express Hotel & Suites Chestertown$91

    Aug 29 - Aug 30

    Holiday Inn Express Hotel & Suites Chestertown$91
    Driftwood Inn

    Driftwood Inn

    609 Washington Avenue, Chestertown, MD
      2.0 out of 5.0
       
       
      2.1 out of 5 (102 reviews)

      Driftwood Inn$56

      Aug 25 - Aug 26

      Driftwood Inn$56

      Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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