Skip to content
77 stays

Stays in Chestertown

Showing you results for "Chestertown, Maryland"
Review COVID-19 travel restrictions before you book.
Learn more
Entire apartment in Chestertown
The Bittersweet
4 guests1 bedroom2 beds1 bath
WifiFree parkingKitchenHeating
Rating 4.72 out of 5;53 reviews
Price:$85 / night
SUPERHOST
Entire guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
2 guests1 bedroom2 beds1 bath
WifiFree parkingKitchenHeating
Rating 4.99 out of 5;81 reviews
Price:$99 / night
SUPERHOST
Entire apartment in Chestertown
Carriage House Hideaway in Middle of Chestertown
2 guestsStudio1 bed1 bath
WifiFree parkingKitchenHeating
Rating 5.0 out of 5;16 reviews
Price:$90 / night
SUPERHOST
Entire cabin in Chestertown
Rivershore Retreat
6 guests2 bedrooms3 beds1.5 baths
WifiFree parkingKitchenHeating
Rating 4.99 out of 5;88 reviews
Price:$294 / night
Entire house in Chestertown
Simple Living on the Pond
4 guests2 bedrooms2 beds1 bath
WifiFree parkingKitchenHeating
Price:$90 / night
SUPERHOST
Entire apartment in Chestertown
Radcliffe Roost: Walk to College & Downtown
4 guests2 bedrooms2 beds1 bath
WifiFree parkingKitchenHeating
Rating 4.97 out of 5;32 reviews
Price:$99 / night
SUPERHOST
Entire guesthouse in Chestertown
Cozy Carriage House
2 guestsStudio1 bed1 bath
WifiFree parkingKitchenHeating
Rating 4.91 out of 5;80 reviews
Price:$89 / night
SUPERHOST
Entire house in Chestertown
Wren Retweet- Country Estate in Center of C’Town
10 guests5 bedrooms6 beds3.5 baths
WifiFree parkingKitchenHeating
Rating 5.0 out of 5;19 reviews
Price:$190 / night
Entire house in Chestertown
Merry Manor Pet Friendly Home
6 guests3 bedrooms4 beds1.5 baths
WifiFree parkingKitchenHeating
Rating 4.85 out of 5;110 reviews
Price:$125 / night
SUPERHOST
Entire house in Chestertown
Town House in the Heart of Chestertown
4 guests2 bedrooms3 beds2.5 baths
WifiKitchenHeating
Rating 4.97 out of 5;123 reviews
Price:$200 / night
SUPERHOST
Entire apartment in Chestertown
RIVER WATCH
4 guests3 bedrooms4 beds1 bath
WifiFree parkingKitchenHeating
Rating 5.0 out of 5;20 reviews
Price:$210 / night
SUPERHOST
Entire house in Chestertown
Duchess of Kent: Walk to downtown & College
12 guests5 bedrooms8 beds2.5 baths
WifiFree parkingKitchenHeating
Rating 5.0 out of 5;53 reviews
Price:$297 / night
Entire cottage in Chestertown
Sunview Cottage on Chesapeake Bay
4 guests2 bedrooms3 beds1 bath
WifiFree parkingKitchenHeating
Rating 4.90 out of 5;122 reviews
Price:$99 / night
Entire house in Chestertown
River cottage with private dock & water fun
10 guests5 bedrooms12 beds3 baths
WifiFree parkingKitchenHeating
Rating 5.0 out of 5;12 reviews
Price:$439 / night
SUPERHOST
Private room in Chestertown
Chestertown - Eastern Shore Getaway
4 guests2 bedrooms3 beds1 private bath
WifiFree parkingHeating
Rating 5.0 out of 5;19 reviews
Price:$99 / night
SUPERHOST
Entire house in Chestertown
Historic Chestertown
5 guests3 bedrooms3 beds2.5 baths
WifiFree parkingKitchenHeating
Rating 4.92 out of 5;121 reviews
Price:$200 / night
SUPERHOST
Entire house in Rock Hall
Bayside Beach House
4 guests2 bedrooms3 beds1.5 baths
WifiFree parkingKitchenHeating
Rating 5.0 out of 5;20 reviews
Price:$175 / night
Entire house in Centreville
very peaceful location (entire place to yourself!)
8 guests4 bedrooms5 beds4 baths
WifiFree parkingKitchenHeating
Rating 4.50 out of 5;46 reviews
Price:$105 / night
Entire house in Chestertown
Historic house on High Street, Chestertown, MD
4 guests2 bedrooms3 beds2.5 baths
WifiFree parkingKitchenHeating
Price:$211 / night
SUPERHOST
Entire house in Chestertown
Classic Victorian in Chestertown
9 guests3 bedrooms7 beds2.5 baths
WifiFree parkingKitchenHeating
Rating 4.96 out of 5;46 reviews
Price:$174 / night
1 20 of 77 places to stay
Enter dates to see full pricing. Additional fees apply. Taxes may be added.