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

RIVER WATCH

3 beds
1 bath
4 guests
Average Price:  
$283
1% More
than normal
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

River Lodge

4 beds
2 baths
10 guests
Average Price:  
$696
8% Cheaper
than normal
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