Bittersweet Guest Suites 
239 High Street
Chestertown, MD 21620

Brampton Inn 
25227 Chestertown Road
Chestertown, MD 21620

Carrousel Horse Bed & Breakfast 
145 North Main Street
Chestertown, MD 21635

Claddaugh Farm Bed & Breakfast 
160 Claddaugh Lane
Chestertown, MD 21620

Comfort Suites Chestertown 
160 Scheeler Road
Chestertown, MD 21620

Great Oak Landing Lodge 
22170 Great Oak Landing Road
Chestertown, MD 21620

Great Oak Manor Inn 
10568 Cliff Road
Chestertown, MD 21620

Hill's Inn Bed & Breakfast 
114 Washington Avenue
Chestertown, MD 21620

Imperial Hotel & Restaurant 
208 High Street
Chestertown, MD 21620

Inn at Mitchell House, The 
8796 Maryland Parkway
Chestertown, MD 21620

Lauretum Inn Bed & Breakfast 
954 High Street
Chestertown, MD 21620

River Inn at Rolph's Wharf 
1008 Rolph's Wharf Road
Chestertown, MD 21620

White Swan Tavern 
231 High Street
Chestertown, MD 21620

Widow's Walk Inn Bed & Breakfast 
402 High Street
Chestertown, MD 21620