Lodging in Chestertown, Maryland

With over 40 bed and breakfasts, motels, hotels, and vacation rentals, Kent County has lodging options for every taste and budget.
Bittersweet Guest Suites
Contact: Mary Maisel
231 High Street
Chestertown, MD 21620
Phone: 410-778-2300
Email: info@whiteswantavern.com
URL: www.whiteswantavern.com
Upstairs over the store in downtown Chestertown
Brampton Bed and Breakfast Inn
Contact: Mike & Danielle Hanscom
25227 Chestertown Road
Chestertown, MD 21620
Phone: 410-778-1860
Email: innkeeper@bramptoninn.com
URL: www.bramptoninn.com
Magnificent national register plantation house on 35 acres.Located just south of the town limits.
Comfort Suites
Contact: Manager
160 Scheeler Road
Chestertown, MD 21620
Phone: 410-810-0555
Email: n/a
URL: www.comfortsuites.com/Maryland
Modern conveniences with 53 rooms. Close to Chestertown's Historic District.
Holiday Inn Express
Contact: Manager
150 Scheeler Road
Chestertown, MD 21620
Phone: 410-778-0778
Email: n/a
URL: www.hiexchestertown.com
Modern convience with 81 rooms. Close to Chestertown's Historic District. Breakfast is complimentary.
John L. Stam House
Contact: Marta Girone
114 Washington Ave
Chestertown, MD 21620
Phone: 410-778-1926
Email: n/a
URL: na
Gothic Revival Victorian, fully restored. Full breakfast and afternoon tea. Within blocks of the Historic District of Chestertown.
Lauretum Bed & Breakfast Inn
Contact: James and Kelly Anthony
954 High Street
Chestertown, MD 21620
Phone: 410-778-3236
Email: innkeeper@lauretuminn.com
URL: www.lauretuminn.com
A long winding lane invites you to Lauretum (1881), sitting splendidly atop a tree graced knoll on six acres in Chestertown, MD. The complex form and massing of the house reflect the eclecticism of the late Victorian period.
Simply Bed & Bread
Contact: Cheryl Hoopes
208 Mt. Vernon Ave.
Chestertown, MD 21620
Phone: 410-778-4359
Email: hbs.hoopes@yahoo.com
URL: simplybedandbread.com/
Two allergy-friendly rooms in a cozy 1947 Cape Cod - a minute's walk from Washington College. "The soul should always stand ajar," [ready to welcome] - Emily Dickinson
Stepne Manor
Contact: Natalie Turner
406 South Cross Street
Chestertown, MD 21620
Phone: 410-810-7591
Email: info@BrittlandEstates.com
URL: www.brittlandestates.com/stepne.html
This historic circa 1690 manor house with wide covered porch is within walking distance to downtown Chestertown. An ideal location for small retreats, meetings and town charm weddings.
White Swan Tavern
Contact: Mary Maisel
231 High Street
Chestertown, MD 21620
Phone: 410-778-2300
Email: info@whiteswantavern.com
URL: www.whiteswantavern.com
Impeccably restored 18th century tavern. "Afternoon tea served daily.
Widow's Walk Inn
Contact: Bob & Susan Lathroum
402 High Street
Chestertown, MD 21620
Phone: 410-778-6455
Email: widwalk@gmail.com
URL: www.widowswalkinn.com
Victorian gem located in Chestertown's Historic District