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Enter dates and number of guests to see the total price per night. Tourism taxes may be added.

46 places to stay

Entire apartment
Rating 4.76 out of 534 reviews
The Bittersweet
4 guests · 1 bedroom · 2 beds · 1 bath
Free parking · Wi-Fi · Kitchen · Heating
Price:$112 CAD/night
Private room
Rating 4.83 out of 56 reviews
Radcliffe Roost: Walk to College & Downtown
4 guests · 2 bedrooms · 2 beds · 1 shared bath
Free parking · Wi-Fi · Kitchen · Heating
Price:$73 CAD/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
Free parking · Wi-Fi · Kitchen · Heating
Price:$104 CAD/night
SUPERHOST
Entire house
Rating 4.95 out of 544 reviews
1880's Beauty in Historic District
5 guests · 2 bedrooms · 3 beds · 2.5 baths
Wi-Fi · Kitchen · Heating
Price:$129 CAD/night
SUPERHOST
Entire guesthouse
Rating 4.89 out of 562 reviews
Cozy Carriage House
2 guests · Studio · 1 bed · 1 bath
Free parking · Wi-Fi · Kitchen · Heating
Price:$112 CAD/night
SUPERHOST
Entire house
Rating 4.92 out of 585 reviews
Merry Manor Pet Friendly Home
6 guests · 3 bedrooms · 4 beds · 1.5 baths
Free parking · Wi-Fi · Kitchen · Heating
Price:$165 CAD/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
Free parking · Wi-Fi · Heating
Price:$91 CAD/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
Free parking · Wi-Fi · Kitchen · Heating
Price:$79 CAD/night
SUPERHOST
Entire guest suite
Rating 5.0 out of 548 reviews
★Beautiful Waterfront Chestertown Getaway
2 guests · 1 bedroom · 2 beds · 1 bath
Free parking · Wi-Fi · Kitchen · Heating
Price:$131 CAD/night
Private room
Rating 5.0 out of 54 reviews
Historic Chestertown Getaway on the Eastern Shore
4 guests · 2 bedrooms · 3 beds · 1 shared bath
Wi-Fi · Heating
Price:$131 CAD/night
SUPERHOST
Entire house
Rating 4.96 out of 5103 reviews
Town House in the Heart of Chestown
4 guests · 2 bedrooms · 3 beds · 2.5 baths
Wi-Fi · Kitchen · Heating
Price:$264 CAD/night
SUPERHOST
Entire cabin
Rating 4.98 out of 554 reviews
Rivershore Retreat
6 guests · 2 bedrooms · 3 beds · 1.5 baths
Free parking · Wi-Fi · Kitchen · Heating
Price:$363 CAD/night
SUPERHOST
Camper/RV
Rating 4.89 out of 548 reviews
Cozy Airstream on a beautiful horse farm
3 guests · 1 bedroom · 2 beds · 1 bath
Free parking · Wi-Fi · Kitchen · Heating
Price:$131 CAD/night
Entire apartment
Rating 5.0 out of 513 reviews
RIVER WATCH
4 guests · 3 bedrooms · 4 beds · 1 bath
Free parking · Wi-Fi · Kitchen · Heating
Price:$277 CAD/night
Hotel room
Simone's Retreat - Brampton Bed and Breakfast Inn
2 guests · 1 bedroom · 1 bed · 1 bath
Free parking · Wi-Fi · Heating
Price:$197 CAD/night
SUPERHOST
Entire house
Rating 5.0 out of 527 reviews
Duchess of Kent: Walk to downtown & College
10 guests · 5 bedrooms · 4 beds · 2.5 baths
Free parking · Wi-Fi · Kitchen · Heating
Price:$264 CAD/night
Entire bungalow
Rating 4.86 out of 537 reviews
Allie's Bungalow
6 guests · 2 bedrooms · 4 beds · 1.5 baths
Wi-Fi · Kitchen · Heating
Price:$178 CAD/night
Entire house
Rating 5.0 out of 53 reviews
Upscale house in center of the town of Chestertown
10 guests · 4 bedrooms · 4 beds · 3.5 baths
Free parking · Wi-Fi · Kitchen · Heating
Price:$200 CAD/night
118 of 46 Rentals
Enter dates to see full pricing. Additional fees apply. Taxes may be added. Free cancellation only applicable within 48 hours from booking.