Hotels, Motels, Inns, B&B's, Resorts And Extended Stay in Chestertown, Maryland
There are 15 properties listed under Hotels, Motels and Extended Stay Suites in Chestertown available. All distances are from the center of Chestertown, so actual travel times may vary.
Hotel
Located 2 miles from the center of Chestertown. Red Roof Inn & Suites Chestertown is one of the best budget hotels in Chestertown, MD that is conveniently located near the crossroads of MD 213 and MD 291.
We offer our guests free Wi-Fi, a guest coin laundry facility and free coffee in the lobby.
160 Scheeler Road
Chestertown, Maryland
Hotel
★★
Located 2 miles from the center of Chestertown. Whether you're looking for a hotel with convenient access to the Great Outdoors, or you're just passing through on your way to D.C.
150 Scheeler Road
Chestertown, Maryland
Bed & Breakfast
Located 6 miles from the center of Chestertown. A Place for all Seasons - Any time can be a memorable one at Great Oak.
10568 Cliff Road
Chestertown, Maryland
Bed & Breakfast
Located 1 mile from the center of Chestertown. The White Swan Tavern has been a familiar landmark in Chestertown since pre-Revolutionary War days.
231 High Street
Chestertown, Maryland
Bed & Breakfast
Located 6 miles from the center of Chestertown. Conveniently located on Maryland's Eastern Shore between Chestertown and Rock Hall in Kent County, this lovely 18th century manor home sits like a jewel on 12 manicured acres.
8796 Maryland Parkway
Chestertown, Maryland
Located 6 miles from the center of Chestertown. Come for the boating – stay for the fun!
With 350 boat slips, a 28-room lodge and 70 acres on Fairlee Creek, Mears Great Oak Landing has everything you need to get away from it all.
22170 Great Oak Landing Road
Chestertown, Maryland
Bed & Breakfast
Located 1 mile from the center of Chestertown. Two bright, spacious, allergy-friendly rooms in a cozy 1947 Cape Cod on MD's Eastern Shore near the Chesapeake Bay..
208 Mount Vernon Avenue
Chestertown, Maryland
Bed & Breakfast
★★★
Located 2 miles from the center of Chestertown. The award-winning Brampton Bed & Breakfast Inn, offers large rooms with luxurious bath rooms and fireplaces and is decorated with antiques and period pieces without compromising the comfort of our guests.
Located less than a mile from historic .....
25227 Chestertown Road
Chestertown, Maryland
Bed & Breakfast
Located 1 mile from the center of Chestertown. The John L. Stam House was built in the late 185os by John and Louise Stam on property owned by Washington College. John Stam was a wealthy entrepreneur who envisioned a “grand colonnade” lined with fine homes which would connect Washington College to downtown Chestertown.
114 Washington Avenue
Chestertown, Maryland
Hotel
6336 Church Hill Road
Chestertown, Maryland
Bed & Breakfast
Located 2 miles from the center of Chestertown. Claddaugh Farm Bed & Breakfast is located 12 miles north of Centerville, Maryland and just 2 miles south of Historic Chestertown, Maryland.
Claddaugh Farm Bed and Breakfast is just one hour by car from Annapolis, Maryland, Easton, Maryland and Dover Delaware.
160 Claddaugh Lane
Chestertown, Maryland
Hotel
★★★
Located 1 mile from the center of Chestertown. Escape from the busy hustles and stress of life and let us pamper you at Driftwood Inn.
609 Washington Avenue
Chestertown, Maryland
Located 1 mile from the center of Chestertown. For over a century The Imperial Hotel has been a gathering place for travelers and local patrons in Chestertown.
208 High Street
Chestertown, Maryland
Bed & Breakfast
Located 2 miles from the center of Chestertown. With views of the Chester River and the adjoining farm, the River Inn at Rolph’s Wharf offers you the opportunity to spend a relaxing night or two away from the everyday. Each of the rooms has its own charming atmosphere that ensures you’ll get a restful night.
1008 Rolph's Wharf Road
Chestertown, Maryland
Bed & Breakfast
Located 1 mile from the center of Chestertown. At the Inn, you will find comfortable lodging with the atmosphere and warmth of a family home. The Inn is furnished with an eclectic collection of antiques and family treasures.
402 High Street
Chestertown, Maryland
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