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
$290/night

Rivershore Retreat

2 beds
1.5 baths
6 guests
Average Price:  
$322
10% Cheaper
than normal
AirDNA Score: 84
$140/night

Cozy Carriage House

studio
1 bath
2 guests
Average Price:  
$120
17% More
than normal
AirDNA Score: 84
$99/night

Beautiful Waterfront Chestertown Getaway

1 bed
1 bath
2 guests
Average Price:  
$123
20% Cheaper
than normal
AirDNA Score: 80
$218/night

Classic Victorian in Chestertown

3 beds
2.5 baths
9 guests
Average Price:  
$253
14% Cheaper
than normal
AirDNA Score: 77
$124/night

Cozy Airstream on a beautiful horse farm

1 bed
1 bath
3 guests
Average Price:  
$142
13% Cheaper
than normal
AirDNA Score: 75
$425/night

Waterfront w/Pier &Walking Distance to Chestertown

4 beds
3 baths
8 guests
Average Price:  
$537
21% Cheaper
than normal
AirDNA Score: 71
$108/night

Sunview Cottage on Chesapeake Bay

2 beds
1 bath
4 guests
Average Price:  
$153
29% Cheaper
than normal
AirDNA Score: 71
$363/night

Historic Chestertown

3 beds
2.5 baths
5 guests
Average Price:  
$358
1% More
than normal
AirDNA Score: 71
$435/night

Duchess of Kent: Walk to downtown & College

5 beds
2.5 baths
12 guests
Average Price:  
$422
3% More
than normal
AirDNA Score: 65
$750/night

Piney Grove Farm

5 beds
3 baths
12 guests
Average Price:  
$771
3% Cheaper
than normal
AirDNA Score: 63
$350/night

3 BR Patriot House- UNIT ONE /Mid-Century Modern

3 beds
1 bath
6 guests
Average Price:  
$385
9% Cheaper
than normal
AirDNA Score: 60
$285/night

RIVER WATCH

3 beds
1 bath
4 guests
Average Price:  
$282
1% More
than normal
AirDNA Score: 58
$190/night

Quiet Cottage on Heron Pond

2 beds
1 bath
4 guests
Average Price:  
$211
10% Cheaper
than normal
AirDNA Score: 58
$85/night

The Bittersweet

1 bed
1 bath
4 guests
Average Price:  
$85
0% Cheaper
than normal
AirDNA Score: 58
$500/night

Private salt pool & spacious getaway Chestertown

4 beds
3 baths
8 guests
Average Price:  
$544
8% Cheaper
than normal
AirDNA Score: 57
$960/night

Stepne Manor

5 beds
3.5 baths
15 guests
Average Price:  
$992
3% Cheaper
than normal
AirDNA Score: 57
$750/night

GREAT OAK GUEST HOUSE BEST- GATED PROPERTY

3 beds
2 baths
8 guests
Average Price:  
$784
4% Cheaper
than normal
AirDNA Score: 57
$638/night

River Lodge

4 beds
2 baths
10 guests
Average Price:  
$662
4% Cheaper
than normal
AirDNA Score: 50
$388/night

Patriot House - Unit Two

3 beds
2 baths
7 guests
Average Price:  
$434
11% Cheaper
than normal
AirDNA Score: 41
$425/night

The Patriot House-Chestertown, MD

6 beds
3 baths
13 guests
Average Price:  
$592
28% Cheaper
than normal
AirDNA Score: 5
$2655/night

Brittland Manor

11 beds
8.5 baths
16 guests
Average Price:  
$2577
3% More
than normal