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We have 6 hotels in Chestertown.

 
 
Comfort Suites Chestertown Star Rating 3        
160 Scheeler Rd.

This relaxed all-suite hotel is 2 miles from both the Chestertown Historic District and Wilmer Park, and 8 miles from Worton Creek Marina.Casual suites feature free Wi-Fi and flat-screen TVs, plus coffeemakers, microwaves and minifridges. Some add pull-out sofas and/or whirlpool tubs.
Holiday Inn Express Hotel & Suites Chestertown Star Rating 2        
150 Scheeler Road

Set in a suburban shopping area half a mile from Washington College, this modern hotel is 1 mile from Chestertown's town center and 2 miles from the Chester River.Classic rooms come with minifridges, microwaves, work desks, flat-screen TVs and free WiFi. Suites add pull-out sofas and kitchenettes, plus kids 19 and under stay free with an adult.
Driftwood Inn Star Rating 2        
609 Washington Avenue

Off Highway 291, this low-key hotel is 1 mile from the Historic District and Wilmer Park, and 5 miles from Thornton, an 18th-century farm.Modest rooms come with free Wi-Fi and TVs, plus microwaves, minifridges and coffeemakers; some have whirlpool tubs. Suites add sitting areas with pull-out sofas.
John L Stam House        
114 Washington Ave

John L Stam House is a great choice for a stay in Chestertown. Free perks include WiFi, self parking, and full breakfast daily between 7 AM and 9:30 AM..
Simply Bed & Bread        
208 Mt Vernon Ave

Simply Bed & Bread is set in Chestertown and is close to local landmarks, such as Washington College and Chestertown Railroad Station. It is ideally positioned for guests wanting to discover the area's attractions.There are 2 rooms at the hotel, each offering all the necessities to ensure a comfortable stay.
Brampton Bed and Breakfast Inn Star Rating 5        
25227 Chestertown Road

Set on a peach plantation that dates from 1860, this refined inn is 2.2 miles from Chestertown Historic District and 18.8 miles from the Eastern Neck National Wildlife Refuge.
 
 
More on Chestertown .
 
Chestertown is a town in Kent County, Maryland, United States. The population was 5,252 at the 2010 census. It is the county seat of Kent County.