The Imperial Hotel
208 high street, (http://www.imperialcheste...). popular with the locals as well as tourists. built in 1903, the imperial hotel has become a significant landmark in chestertown and a must-see for many tourists. the front room restaurant serves lunch and dinner tuesday through saturday and brunch on sunday. the hotel has 11 rooms and 2 suites. something unique about the imperial hotel is that each room has its own individual interior, furnished with authentic period furnishings and antiques.
Brampton Bed & Breakfast Inn
25227 chestertown road, (http://www.bramptoninn.com/) a quiet yet modernly equipped 19'th century luxury estate settled on 25 landscaped acres. located just outside of chestertown. ranked #1 by trip advisor and on national geographic's stay list for north america.
Holiday Inn Express
150 scheeler road, [www.hiexpress.com] comfortable accommodations for families, couples, business travlers, etc. amenities include and indoor swimming pool, fitness center and complimentary continental breakfast.
Great Oak Manor
10568 cliff road, [1] this bed and breakfast is ideal for secluded getaways to the chesapeake bay area. far from any highway or large towns, our inn will relax you with the sounds of nature, the aura of yesteryear, and the comforts of modern society.