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

Stepne Manor

5 beds
3.5 baths
15 guests
Average Price:  
$987
3% Cheaper
than normal
AirDNA Score: 57
$600/night

River Lodge

4 beds
2 baths
10 guests
Average Price:  
$642
7% Cheaper
than normal
AirDNA Score: 5
$1750/night

Brittland Manor

11 beds
8.5 baths
16 guests
Average Price:  
$2499
30% Cheaper
than normal