| Business | Phone |
| Comfort Suites 160 Scheeler Rd, Chestertown 21620 | (410) 810-0555 |
| Courtyard Inn Motel 6336 Church Hill Rd, Chestertown 21620 | (410) 778-2755 |
| Great Oak Landing Lodge 22170 Great Oak Landing Rd, Chestertown 21620 | (410) 778-2100 |
| Imperial Hotel 208 High St, Chestertown 21620 | (410) 778-5000 |
| Brampton Bed & Breakfast Inn 25227 Chestertown Road, Chestertown 21620 | (410) 778-1860 |