Lodging in the Chestertown Area

With over 40 bed and breakfasts, motels, hotels, and vacation rentals, Kent County has lodging options for every taste and budget.
Crow Farm Stay B & B
Contact:  Judy Crow
12441 Vansants Corner Road
Kennedyville, MD  21645
Phone: 410-648-5687
Email: crowfarmmd@gmail.com
URL: www.crowfarmmd.com
Enjoy a unique farm experience. Walk the trails on our 365 acre farm, enjoy views of the vineyard and forever fields. We're located about an hour from Baltimore, Washington, Philadelphia, Wilmington and minutes from historic Chestertown on Maryland's Eastern Shore. Wine Tasting Room open weekends 12-6pm.
Great Oak Manor
Contact:  Jennifer Donisi
10568 Cliff Road
Chestertown, MD  21620
Phone: 410-778-5943
Email: info@greatoakmd.com
URL: www.greatoakmd.com
Elegant 12 room Waterfront Manor House with spectacular Chesapeake Bay sunsets off a private beach. Located 8.5 miles from Chestertown.
Inn at Mitchell House
Contact:  Jim and Tracy Stone
8796 Maryland Parkway
Chestertown, MD  21620
Phone: 410-778-6500
Email: innkeeper@innatmitchellhouse.com
URL: www.innatmitchellhouse.com
Beauty undisturbed. Historic manor offers a tranquil retreat. Approximately 10 miles outside of Chestertown.
Kitty Knight House
Contact:  Sandy
14028 Augustine Herman Highway
Georgetown, MD  21930
Phone: 410-648-5200
Email: restaurant@kittyknight.com
URL: www.kittyknight.com
18th Century Charm in the 21st Century. The Kitty Knight House & Deck feature traditional Eastern Shore cuisine with a historical touch. The Kitty Knight Inn features eleven beautifully appointed rooms.
Mears Great Oak Landing
Contact:  Mary McAllister
22170 Great Oak Landing Road
Chestertown, MD  21620
Phone: 410-778-5007
Email: info@mearsgreastoaklanding.com
URL: www.mearsgreatoaklanding.com
28 Modern Rooms, Casual Fine Dining, Swimming Pool and Golf Course. Located approximately 10 miles from Chestertown.
River Inn at Rolph's Wharf
Contact:  Innkeeper
1008 Rolph's Wharf Rd
Chestertown, MD  21620
Phone: 800-894-6347
Email: rolphs@aol.com
URL: www.rolphswharf.com
Victorian Farmhouse on the shores of the Chester River. Approximately 3 miles from Chestertown.
River Lodge
Contact:  Natalie Turner
219 Brittland Farm Lane
Chestertown, MD  21620
Phone: 410-810-7591
Email: info@BrittlandEstates.com
URL: www.brittlandestates.com/lodge.html
With its rustic, peaceful waterfront setting, the River Lodge is an excellent venue for a business retreat, private getaway, family reunion, or informal wedding; a four season destination. The Lodge is perched on the banks of the Chester River and includes a dock, front and back porches, a great room, sleeping for 9-11 people, and kitchen facilities.
Running Fox
Contact:  Natalie Turner
23791 Ricauds Branch Road
Chestertown, MD  21620
Phone: 410-810-7591
Email: info@BrittlandEstates.com
URL: www.brittlandestates.com/runningFox.html
This countryside property with wildlife pond and woodside fields, includes a two-story historic house and barn. Kitchen is fully equipped and modernized with adjacent dining. Upstairs houses 3 bedrooms and an interesting back wing bedroom perfect for children. Ideal for romantic get-a-ways, retreats, hunting parties or a country wedding.