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Explore Chestertown

Where to stay

Entire apartment · 2 beds
Rating 4.77 out of 5
The Bittersweet
Price:$113 CAD/night
SUPERHOST
Entire guest suite · 2 beds
Rating 5.0 out of 5
★Beautiful Waterfront Chestertown Getaway
Price:$131 CAD/night
SUPERHOST
Camper/RV · 2 beds
Rating 4.89 out of 5
Cozy Airstream on a beautiful horse farm
Price:$131 CAD/night
Private room · 2 beds
Rating 4.83 out of 5
Radcliffe Roost: Walk to College & Downtown
Price:$73 CAD/night
SUPERHOST
Private room · 1 bed
Rating 4.96 out of 5
1 Small Bedroom with private bath on Chester River
Price:$99 CAD/night
SUPERHOST
Entire apartment · 1 bed
Rating 4.50 out of 5
Charming 2nd Floor Apartment in Chestertown
Price:$105 CAD/night
SUPERHOST
Entire cottage · 3 beds
Rating 4.93 out of 5
Sunview Cottage on Chesapeake Bay
Price:$130 CAD/night
SUPERHOST
Entire house · 3 beds
Rating 4.95 out of 5
1880's Beauty in Historic District
Price:$130 CAD/night
SUPERHOST
Entire house · 4 beds
Rating 4.92 out of 5
Merry Manor Pet Friendly Home
Price:$166 CAD/night
SUPERHOST
Entire guesthouse · 1 bed
Rating 4.89 out of 5
Cozy Carriage House
Price:$113 CAD/night

Stay with a Superhost

Make yourself at home with these experienced hosts
SUPERHOST
Camper/RV · 2 beds
Rating 4.89 out of 5
Cozy Airstream on a beautiful horse farm
Price:$131 CAD/night
SUPERHOST
Entire guest suite · 2 beds
Rating 5.0 out of 5
★Beautiful Waterfront Chestertown Getaway
Price:$131 CAD/night
SUPERHOST
Private room · 1 bed
Rating 4.96 out of 5
1 Small Bedroom with private bath on Chester River
Price:$99 CAD/night
SUPERHOST
Entire apartment · 1 bed
Rating 4.50 out of 5
Charming 2nd Floor Apartment in Chestertown
Price:$105 CAD/night
SUPERHOST
Entire cottage · 3 beds
Rating 4.93 out of 5
Sunview Cottage on Chesapeake Bay
Price:$130 CAD/night
SUPERHOST
Entire house · 3 beds
Rating 4.95 out of 5
1880's Beauty in Historic District
Price:$130 CAD/night
SUPERHOST
Entire house · 4 beds
Rating 4.92 out of 5
Merry Manor Pet Friendly Home
Price:$166 CAD/night
SUPERHOST
Entire guesthouse · 1 bed
Rating 4.89 out of 5
Cozy Carriage House
Price:$113 CAD/night
SUPERHOST
Entire cottage · 4 beds
Rating 4.94 out of 5
Cottage with Modern Updates - Walk to Waterfront!
Price:$199 CAD/night
SUPERHOST
Private room · 1 bed
Rating 5.0 out of 5
A Simple Stay...next door to Washington College
Price:$91 CAD/night

Places to stay with a pool

22% of guests who visited Baltimore last year searched for a place to stay with a pool
SUPERHOST
Private room · 1 bed
Rating 4.91 out of 5
Pet Friendly Light House
Price:$60 CAD/night
SUPERHOST
Private room · 1 bed
Rating 4.91 out of 5
Chesapeake Mornings
Price:$66 CAD/night
Shared room · 1 bed
Quiet in the country stay
Price:$27 CAD/night