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Check prices for these dates

Next weekend
26 Dec - 28 Dec
In two weeks
2 Jan - 4 Jan
In one month
16 Jan - 18 Jan
In two months
13 Feb - 15 Feb

Our top choices for Chestertown condo rentals

Fridge, microwave, oven, stovetop
Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
Historic Row Home in Downtown Annapolis
Dining
Luxury Baltimore Escape

Luxury Baltimore Escape

Luxury Baltimore Escape
2.0 star property
Canton
The price is AED 2,020
AED 3,428 total
includes taxes & fees
14 Jan - 15 January 2026
Luxury Baltimore Escape
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

Holiday Inn Express White Marsh by IHG

Holiday Inn Express White Marsh by IHG

10/10 Excellent
"Clean and confortable"
Alberto 1-night trip
Posted 2 days ago
Holiday Inn Express White Marsh by IHG

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