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Vacation Rentals in Chestertown, Maryland

about Chestertown

This section features the following homes, villas, cabins, cottages or condos listed below. Please click on the description to view any of the Chestertown rentals you see listed for more information. Vacation rentals in Chestertown, Maryland are added and updated every week, so please bookmark us and visit again.

Chestertown, Maryland Vacation Rentals and Tourism

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Check out more areas which feature homes, villas, cabins, cottages, or condos.

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* Nightly rates and average rates per bedroom are based on actual rates in this area. Learn More .

Cottage on the Sassafras
Chestertown House Rental Picture
  • bedrooms 2
  • sleeps 5
  • community Kentmore Park
  • baths 1
  • rental type House
  • rates (USD) $850 - $900 /wk