The Best Airbnb Deals in
Chestertown, Maryland

Save money on your trip by finding the biggest discounts for top-rated Airbnb rentals in Chestertown, Maryland. Enter your travel dates to find the best deals!

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AirDNA Score: 71
$326/night

Historic Chestertown

3 beds
2.5 baths
5 guests
Average Price:  
$360
9% Cheaper
than normal
AirDNA Score: 65
$751/night

Piney Grove Farm

5 beds
3 baths
12 guests
Average Price:  
$810
7% Cheaper
than normal
AirDNA Score: 59
$632/night

Chestertown Watson Family Farm

5 beds
3 baths
9 guests
Average Price:  
$593
7% More
than normal
AirDNA Score: 50
$374/night

Patriot House - Unit Two

3 beds
2 baths
7 guests
Average Price:  
$413
9% Cheaper
than normal
AirDNA Score: 41
$350/night

The Patriot House-Chestertown, MD

6 beds
3 baths
13 guests
Average Price:  
$519
33% Cheaper
than normal
AirDNA Score: 5
$2722/night

Celebrate Memorial Weekend at a Beautiful Estate

11 beds
8.5 baths
16 guests
Average Price:  
$2795
3% Cheaper
than normal
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