| Business | Phone |
| Claddaugh Farm Bed & Breakfast 160 Claddaugh Ln, Chestertown 21620 | (410) 778-4894 |
| Driftwood Inn 609 Washington Ave, Chestertown 21620 | (410) 778-3200 |
| Great Oak Manor B & B 10568 Cliff Rd, Chestertown 21620 | (410) 778-5943 |
| Hill's Inn 114 Washington Ave, Chestertown 21620 | (410) 778-1926 |
| Inn At Mitchell House 8796 Maryland Pkwy, Chestertown 21620 | (410) 778-6500 |
| Lauretum Inn 954 High St, Chestertown 21620 | (410) 778-3236 |
| Mattie Dean Bed & Breakfast 206 Washington Ave, Chestertown 21620 | (410) 810-0900 |
| Parker House 108 Spring Ave, Chestertown 21620 | (410) 778-9041 |
| River Inn At Rolph's Wharf 1008 Rolphs Wharf Rd, Chestertown 21620 | (410) 778-6347 |
| White Swan Tavern 228 Cannon St, Chestertown 21620 | (410) 778-2300 |
| Widow's Walk Inn B & B 402 High St, Chestertown 21620 | (410) 778-6864 |
| Brampton Bed & Breakfast Inn 25227 Chestertown Road, Chestertown 21620 | (410) 778-1860 |