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: 84
$85/night
Cozy Carriage House
studio
1 bath
2 guests
Average Price:
$113
25% Cheaper
than normal
AirDNA Score: 83
$500/night
Entire River Front Home - 4 Bedrooms 4.5 Baths
4 beds
4.5 baths
10 guests
Average Price:
$550
9% Cheaper
than normal
AirDNA Score: 77
$109/night
Cozy Airstream on a beautiful horse farm
1 bed
1 bath
3 guests
Average Price:
$146
25% Cheaper
than normal
AirDNA Score: 71
$275/night
Historic Chestertown
3 beds
2.5 baths
5 guests
Average Price:
$357
23% Cheaper
than normal
AirDNA Score: 71
$550/night
Duchess of Kent: Walk to downtown & College
5 beds
2.5 baths
12 guests
Average Price:
$356
54% More
than normal
AirDNA Score: 65
$600/night
Piney Grove Farm
5 beds
3 baths
12 guests
Average Price:
$651
8% Cheaper
than normal
AirDNA Score: 58
$190/night
Quiet Cottage on Heron Pond
2 beds
1 bath
4 guests
Average Price:
$215
12% Cheaper
than normal
AirDNA Score: 58
$500/night
Private salt pool & spacious getaway Chestertown
4 beds
3 baths
8 guests
Average Price:
$482
4% More
than normal
AirDNA Score: 57
$750/night
GREAT OAK GUEST HOUSE BEST- GATED PROPERTY
3 beds
2 baths
8 guests
Average Price:
$792
5% Cheaper
than normal
AirDNA Score: 57
$960/night
AirDNA Score: 57
$600/night
AirDNA Score: 5
$1750/night
Brittland Manor
11 beds
8.5 baths
16 guests
Average Price:
$2499
30% Cheaper
than normal