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Featured Chestertown Hotels with a Pool
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
Fully refundable
Book a stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
Fully refundableReserve now, pay when you stay
Stay at this hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
Driftwood Inn
609 Washington Avenue Chestertown MD
Fully refundableReserve now, pay when you stay
Stay at this motel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Larrabee Arts Center and Rolling Road Park are ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Hotels by Star Rating
More Hotel Options in Chestertown
- Hotels with Free Parking in Chestertown
- Romantic Hotels in Chestertown
- Family Hotels in Chestertown
- Pet-friendly Hotels in Chestertown
- Beach Hotels in Chestertown
- Apartment Hotel in Chestertown
- Historic Hotels in Chestertown
- Hotel Wedding Venues in Chestertown
- Hotels with an Indoor Pool in Chestertown
- Resorts & Hotels with Spas in Chestertown
Top Points of Interests in Chestertown
- Hotels near Washington College
- Hotels near Rolphs Wharf Marina
- Hotels near Historical Society of Kent County Maryland
- Hotels near River Arts Chestertown
- Hotels near Garfield Center for the Arts at the Prince Theater
- Hotels near Wilmer Park
- Hotels near Crumpton Auction
- Hotels near Sumner Hall
- Hotels near Baltimore Cruise Terminal
- Hotels near U.S. Naval Academy
- Hotels near Chesapeake Bay
- Hotels near Annapolis City Dock
- Hotels near Chesapeake Bay Bridge
- Hotels near Sandy Point State Park
- Hotels near Ripken Stadium
- Hotels near Fort McHenry
- Hotels near Susquehanna River
Cities near Chestertown
- Annapolis Hotels (28.1 mi)
- Dover Hotels (29.45 mi)
- St. Michaels Hotels (30.99 mi)
- Delaware Beaches Hotels (43.94 mi)
- Easton Hotels (30.7 mi)
- Aberdeen Hotels (20.7 mi)
- Glen Burnie Hotels (29.99 mi)
- Elkton Hotels (29.71 mi)
- Perryville Hotels (23.56 mi)
- Stevensville Hotels (21.06 mi)
- Middletown Hotels (24.66 mi)
- Edgewood Hotels (18.31 mi)
- Bel Air Hotels (26.49 mi)
- Havre De Grace Hotels (22.85 mi)
- White Marsh Hotels (21.43 mi)
- North East Hotels (27.19 mi)
- Grasonville Hotels (19.53 mi)
- Eastern Shore Hotels (40.21 mi)
- Pasadena Hotels (26.32 mi)
- Parkville Hotels (27.43 mi)
Most Booked Hotels in Chestertown
- Comfort Inn & Suites Chestertown
- Historic Inns of Annapolis
- Hampton Inn Baltimore/Glen Burnie
- La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
- Best Western Plus Hotel & Conference Center
- Pendry Baltimore
- Hilton Garden Inn Baltimore/White Marsh
- Hampton Inn Baltimore Bayview Campus
- Hampton Inn Baltimore/White Marsh
- Fairfield Inn & Suites by Marriott White Marsh
- La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
- Americas Best Value Inn Edgewood
- Hampton Inn & Suites Edgewood/Aberdeen-South
- Annapolis Waterfront Hotel, Autograph Collection