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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.
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More Hotel Options in Chestertown
- Hotels with Free Parking in Chestertown
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- Pet-friendly Hotels in Chestertown
- Beach Hotels in Chestertown
- Apartment Hotels in Chestertown
- Historic Hotels in Chestertown
- Hotel Wedding Venues in Chestertown
- Hotels with an Indoor Pool in Chestertown
- Resorts & Hotels with Spas in Chestertown
Other Options
Top Points of Interests in Chestertown
- Hotels near Washington College
- Hotels near Rolphs Wharf Marina
- Hotels near River Arts Chestertown
- Hotels near Historical Society of Kent County Maryland
- Hotels near Garfield Center for the Arts at the Prince Theater
- Hotels near Crumpton Auction
- Hotels near Sumner Hall
- Hotels near Wilmer Park
- Hotels near Chestertown Farmers Market
- Hotels near Schooner Sultana
- Hotels near Chesapeake Bay
- Hotels near Northern Chesapeake Bay
Cities near Chestertown
- Annapolis Hotels (28.1 mi)
- Dover Hotels (29.45 mi)
- St. Michaels Hotels (30.99 mi)
- Easton Hotels (30.7 mi)
- Havre De Grace Hotels (22.85 mi)
- Aberdeen Hotels (20.7 mi)
- Elkton Hotels (29.71 mi)
- Middletown Hotels (24.66 mi)
- Glen Burnie Hotels (29.99 mi)
- Perryville Hotels (23.56 mi)
- Stevensville Hotels (21.06 mi)
- Edgewood Hotels (18.31 mi)
- Bel Air Hotels (26.49 mi)
- Delaware Beaches Hotels (43.94 mi)
- Grasonville Hotels (19.53 mi)
- White Marsh Hotels (21.43 mi)
- North East Hotels (27.19 mi)
- Parkville Hotels (27.43 mi)
- Rock Hall Hotels (10.49 mi)
- Pasadena Hotels (26.32 mi)
Most Booked Hotels in Chestertown
- Comfort Inn & Suites Chestertown
- La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
- Historic Inns of Annapolis
- Best Western Plus Hotel & Conference Center
- Hampton Inn Baltimore/White Marsh
- Pendry Baltimore
- La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
- Hampton Inn Baltimore/Glen Burnie
- The Inn at Chesapeake Bay Beach Club
- Quality Inn & Suites Bel Air I-95 Exit 77A
- Annapolis Waterfront Hotel, Autograph Collection
- Fairfield Inn & Suites by Marriott White Marsh
- Hampton Inn & Suites Edgewood/Aberdeen-South
- Hilton Garden Inn Baltimore/White Marsh