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
$287/night

Rivershore Retreat

2 beds
1.5 baths
6 guests
Average Price:  
$305
6% Cheaper
than normal
AirDNA Score: 77
$113/night

Cozy Airstream on a beautiful horse farm

1 bed
1 bath
3 guests
Average Price:  
$142
20% Cheaper
than normal
AirDNA Score: 75
$490/night

Waterfront w/Pier &Walking Distance to Chestertown

4 beds
3 baths
8 guests
Average Price:  
$559
12% Cheaper
than normal
AirDNA Score: 71
$275/night

Historic Chestertown

3 beds
2.5 baths
5 guests
Average Price:  
$381
28% Cheaper
than normal
AirDNA Score: 71
$320/night

Duchess of Kent: Walk to downtown & College

5 beds
2.5 baths
12 guests
Average Price:  
$524
39% Cheaper
than normal
AirDNA Score: 70
$235/night

Chestertown''s Little Red Cottage, Pet-Friendly

2 beds
1 bath
4 guests
Average Price:  
$259
9% 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:  
$441
32% 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: 58
$500/night

Fall in Chestertown !

4 beds
3 baths
8 guests
Average Price:  
$609
18% Cheaper
than normal
AirDNA Score: 57
$890/night

Stepne Manor

5 beds
3.5 baths
15 guests
Average Price:  
$1016
12% Cheaper
than normal
AirDNA Score: 57
$675/night

River Lodge

4 beds
2 baths
11 guests
Average Price:  
$704
4% Cheaper
than normal
AirDNA Score: 50
$325/night

Patriot House - Unit Two

3 beds
2 baths
7 guests
Average Price:  
$463
30% Cheaper
than normal
AirDNA Score: 41
$625/night

The Patriot House-Chestertown, MD

6 beds
3 baths
13 guests
Average Price:  
$603
4% More
than normal
AirDNA Score: 5
$2200/night

Brittland Manor

11 beds
8.5 baths
16 guests
Average Price:  
$2583
15% Cheaper
than normal