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: 86
$295/night
Rivershore Retreat
2 beds
1.5 baths
6 guests
Average Price:
$304
3% Cheaper
than normal
AirDNA Score: 84
$85/night
Cozy Carriage House
studio
1 bath
2 guests
Average Price:
$119
29% Cheaper
than normal
AirDNA Score: 80
$185/night
Classic Victorian in Chestertown
4 beds
2.5 baths
9 guests
Average Price:
$260
29% Cheaper
than normal
AirDNA Score: 77
$110/night
Cozy Airstream on a beautiful horse farm
1 bed
1 bath
3 guests
Average Price:
$145
24% Cheaper
than normal
AirDNA Score: 75
$425/night
Waterfront w/Pier &Walking Distance to Chestertown
4 beds
3 baths
8 guests
Average Price:
$563
25% Cheaper
than normal
AirDNA Score: 71
$275/night
Historic Chestertown
3 beds
2.5 baths
5 guests
Average Price:
$390
29% Cheaper
than normal
AirDNA Score: 71
$385/night
Duchess of Kent: Walk to downtown & College
5 beds
2.5 baths
12 guests
Average Price:
$522
26% Cheaper
than normal
AirDNA Score: 65
$750/night
Piney Grove Farm
5 beds
3 baths
12 guests
Average Price:
$799
6% Cheaper
than normal
AirDNA Score: 63
$300/night
3 BR Patriot House- UNIT ONE /Mid-Century Modern
3 beds
1 bath
6 guests
Average Price:
$424
29% Cheaper
than normal
AirDNA Score: 60
$414/night
Perfect & private gathering place
5 beds
4 baths
14 guests
Average Price:
$566
27% Cheaper
than normal
AirDNA Score: 60
$285/night
AirDNA Score: 57
$920/night
Stepne Manor
5 beds
3.5 baths
15 guests
Average Price:
$1027
10% Cheaper
than normal
AirDNA Score: 57
$750/night
GREAT OAK GUEST HOUSE BEST- GATED PROPERTY
3 beds
2 baths
8 guests
Average Price:
$825
9% Cheaper
than normal
AirDNA Score: 57
$638/night
AirDNA Score: 51
$119/night
Chestertown - Eastern Shore Getaway
1 bed
1 bath
4 guests
Average Price:
$121
2% Cheaper
than normal
AirDNA Score: 50
$325/night
Patriot House - Unit Two
3 beds
2 baths
7 guests
Average Price:
$452
28% Cheaper
than normal
AirDNA Score: 41
$350/night
The Patriot House-Chestertown, MD
6 beds
3 baths
13 guests
Average Price:
$603
42% Cheaper
than normal
AirDNA Score: 5
$2250/night
Brittland Manor
11 beds
8.5 baths
16 guests
Average Price:
$2597
13% Cheaper
than normal