Chestertown Lodging Options

There are quite a few lodging options in the Chestertown area. Two chain hotels are located near town as well as several bed and breakfast establishments. Vacation home rentals area also available in the Chestertown area.

Chestertown Hotels

Holiday Inn Express Hotel & Suites Chestertown – Located convenient to downtown and Washington College. Free high-speed internet.  Complementary buffet breakfast. Fitness center, indoor pool.  

Quality Suites Chestertown – Located one mile from historic downtown. Heated indoor pool.  Suites with refrigerator, microwave, and coffee maker. Convenient to Washington College. This property was formerly a Comfort Suites.

Chestertown Bed & Breakfasts

• Brampton Bed & Breakfast Inn – Located on 20 wooded acres, just one mile outside of Chestertown, Maryland.   25227 Chestertown Road, Chestertown, MD  21620. TripAdvisor Reviews.
• Great Oak Manor Inn –  Waterfront bed and breakfast on the outskirts of Chestertown. TripAdvisor Reviews 
• The Inn at Mitchell House –  Located between Chestertown and Rock Hall in Kent County.  An 18th Century manor house on 12 manicured acres. TripAdvisor Reviews 
• John Stam House – Four guest rooms in historic downtown Chestertown. 114 Washington Street, Chestertown, MD. TripAdvior Reviews 
• Simply Bed and Bread–  Located 100 yards from the Washington College campus and a 10 minute walk to downtown Chestertown. TripAdvisor Reviews 
• Widow’s Walk Inn –  In Chestertown’s historic district.  Within walking distance of the Chester River, Washington College, shops and restaurants. TripAdvisor Reviews 
• White Swan Tavern–  A restored historic inn.  TripAdvisor Reviews 

Chestertown Vacation Rentals

Get away for a while with a vacation home rental.  Whether you stay for a weekend or a week these home-away-from homes make a wonderful retreat. Choose a large home with lots of bedrooms and recreation area for a family reunion or gathering with friends or a cozy one bedroom cottage for a romantic weekend escape.

• Traditional Home with Midcentury Modern Interior – Three bedrooms, 1 bath. Downtown location, two blocks from High Street restaurants and shops.
• Historic Downtown Chestertown Home with Modern Amenities – Four bedrooms, 2 baths. Within walking distance of shops, restaurants, and waterfront. A short walk to Chestertown Marina.
• Historic Stepne Manor – Five bedroom, 4.5 baths. Adjacent to Wilmer Park, which was originally part of the Stepne Manor property.
• Historic District Home with Large Garden – Five bedrooms, 2 full & 2 half baths. Located two blocks from Washington College and two blocks from the Chestertown waterfront.
• More Chestertown Vacation Rentals – More available Chestertown rental homes to choose from.