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56 places to stay

Private room
Rating 5.0 out of 55 reviews
Radcliffe Roost: Walk to College & Downtown
4 guests · 2 bedrooms · 2 beds · 1 shared bath
Wifi · Kitchen · Free parking
Price:$49 / night
Entire apartment
Rating 4.76 out of 533 reviews
The Bittersweet
4 guests · 1 bedroom · 2 beds · 1 bath
Wifi · Kitchen · Free parking
Price:$85 / night
SUPERHOST
Entire guest suite
Rating 5.0 out of 548 reviews
★Beautiful Waterfront Chestertown Getaway
2 guests · 1 bedroom · 2 beds · 1 bath
Wifi · Kitchen · Free parking
Price:$99 / night
SUPERHOST
Camper/RV
Rating 4.89 out of 547 reviews
Cozy Airstream on a beautiful horse farm
3 guests · 1 bedroom · 2 beds · 1 bath
Wifi · Kitchen · Free parking
Price:$99 / night
SUPERHOST
Private room
Rating 4.96 out of 550 reviews
1 Small Bedroom with private bath on Chester River
2 guests · 1 bedroom · 1 bed · 1.5 baths
Wifi · Kitchen · Free parking
Price:$75 / night
SUPERHOST
Private room
Rating 5.0 out of 521 reviews
A Simple Stay...next door to Washington College
2 guests · 1 bedroom · 1 bed · 1 shared bath
Wifi · Free parking
Price:$69 / night
Private room
Rating 5.0 out of 53 reviews
Private Room w/bath: Walk to Washington College
3 guests · 2 bedrooms · 2 beds · 1 private bath
Wifi · Kitchen · Free parking
Price:$60 / night
SUPERHOST
Entire house
Rating 4.95 out of 542 reviews
1880's Beauty in Historic District
5 guests · 2 bedrooms · 3 beds · 2.5 baths
Wifi · Kitchen
Price:$130 / night
Private room
Rating 4.88 out of 578 reviews
Private Bedroom and bath in Chestertown, MD
2 guests · 1 bedroom · 1 bed · 1 private bath
Wifi · Free parking
Price:$55 / night
SUPERHOST
Entire apartment
Rating 4.63 out of 567 reviews
Cozy 1st Floor Apartment in Chestertown
2 guests · 1 bedroom · 1 bed · 1 bath
Wifi · Kitchen · Free parking
Price:$75 / night
SUPERHOST
Entire house
Rating 4.92 out of 584 reviews
Merry Manor Pet Friendly Home
6 guests · 3 bedrooms · 4 beds · 1.5 baths
Wifi · Kitchen · Free parking
Price:$125 / night
Entire cottage
Rating 4.92 out of 514 reviews
Yellow Door Cottage
4 guests · 2 bedrooms · 2 beds · 1 bath
Wifi · Kitchen · Free parking
Price:$100 / night
Entire apartment
Rating 5.0 out of 513 reviews
RIVER WATCH
4 guests · 3 bedrooms · 4 beds · 1 bath
Wifi · Kitchen · Free parking
Price:$210 / night
SUPERHOST
Entire apartment
Rating 4.50 out of 5107 reviews
Charming 2nd Floor Apartment in Chestertown
2 guests · 1 bedroom · 1 bed · 1 bath
Wifi · Kitchen · Free parking
Price:$79 / night
Private room
Rating 5.0 out of 53 reviews
Historic Chestertown Getaway on the Eastern Shore
4 guests · 2 bedrooms · 3 beds · 1 shared bath
Wifi
Price:$99 / night
Hotel room
Simone's Retreat - Brampton Bed and Breakfast Inn
2 guests · 1 bedroom · 1 bed · 1 bath
Wifi · Free parking
Price:$149 / night
SUPERHOST
Entire guesthouse
Rating 4.89 out of 561 reviews
Cozy Carriage House
2 guests · Studio · 1 bed · 1 bath
Wifi · Kitchen · Free parking
Price:$85 / night
SUPERHOST
Private room
Rating 4.96 out of 526 reviews
2 Bedroom Suite-Private Bath on Chester River
4 guests · 2 bedrooms · 3 beds · 1 private bath
Wifi · Kitchen · Free parking
Price:$155 / night
1 18 of 56 Rentals
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