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Compare Condo Rentals in Chestertown with updated reviews, rates, and availability.

Annapolis Condominium in the heart of the historic center
Annapolis Condominium in the heart of the historic center
9.8 out of 10, Exceptional, (269)

Kent Island Waterfront Cottage
Kent Island Waterfront Cottage
9.4 out of 10, Exceptional, (8)

BEACH WITHOUT THE BUSTLE
BEACH WITHOUT THE BUSTLE
10.0 out of 10, Exceptional, (26)

Delightful little Historic District gem - for the antique lover and history buff.
Delightful little Historic District gem - for the antique lover and history buff.
9.0 out of 10, Wonderful, (4)
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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Other property types in Chestertown

First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (79)
The price is SAR 368
SAR 592 total
includes taxes & fees
5 Mar - 6 Mar

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
9.4 out of 10, Exceptional, (22)

Captivating Chesapeake experience
Captivating Chesapeake experience
10.0 out of 10, Exceptional, (256)
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.
Recent reviews of Chestertown hotels
Recent reviews of Chestertown hotels

Hilton Garden Inn Baltimore/White Marsh
5/5 Excellent
Relaxed
"All was on point and appreciated the hour earlier check in so i could relax before first meeting.
Staff very nice and very helpful.
Loved the text asking if i was comfortable a few hours into the stay."
A verified traveler stayed at Hilton Garden Inn Baltimore/White Marsh
Posted 4 hours ago
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