An aerial view of a town with a river, buildings, and surrounding greenery.

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Chestertown cottages

House (3 Bedrooms) | Interior

1. Idyllic Pasadena Retreat With Garden + Hot Tub!

Idyllic Pasadena Retreat With Garden + Hot Tub!
3.0 star property
Green Haven
The price is AU$687
includes taxes & fees
12 Aug - 13 Aug
Idyllic Pasadena Retreat With Garden + Hot Tub!
House (3 Bedrooms) | Interior

2. Waterfront Home on Marley Creek!

Waterfront Home on Marley Creek!
3.0 star property
Marley
The price is AU$647
includes taxes & fees
12 Aug - 13 Aug
Waterfront Home on Marley Creek!
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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Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Hotel staff were great as well as valet! Very convenient to downtown Annapolis!"
Colleen 1-night trip
Posted 7 hours ago
Historic Inns of Annapolis

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
Accommodation
61 Cottages
Lowest Price
AU$647
Highest Price
AU$687

Frequently asked questions

What is there to do in Chestertown near my cottage?
The ideal travel accessory is a well-planned itinerary. Historical Society of Kent County Maryland is an excellent place to start your exploration of Chestertown.