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Featured Chestertown Hotels with a Pool
Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
Fully refundableReserve now, pay when you stay
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
Stay at this motel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Rolling Road Park and Historical Society of Kent ...
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 Wilmer Park
- Hotels near Crumpton Auction
- Hotels near Garfield Center for the Arts at the Prince Theater
- Hotels near Sumner Hall
- Hotels near Baltimore Cruise Terminal
- Hotels near U.S. Naval Academy
- Hotels near Navy-Marine Corps Memorial Stadium
- Hotels near Ripken Stadium
- Hotels near Chesapeake Bay Bridge
- Hotels near Annapolis City Dock
- Hotels near Chesapeake Bay
- Hotels near Sandy Point State Park
- Hotels near Susquehanna River
- Hotels near White Marsh Mall
Cities near Chestertown
- Annapolis Hotels (28.1 mi)
- Dover Hotels (29.45 mi)
- St. Michaels Hotels (30.99 mi)
- Aberdeen Hotels (20.7 mi)
- Easton Hotels (30.7 mi)
- Elkton Hotels (29.71 mi)
- Edgewood Hotels (18.31 mi)
- Perryville Hotels (23.56 mi)
- Bel Air Hotels (26.49 mi)
- Middletown Hotels (24.66 mi)
- White Marsh Hotels (21.43 mi)
- Glen Burnie Hotels (29.99 mi)
- Havre De Grace Hotels (22.85 mi)
- Stevensville Hotels (21.06 mi)
- Delaware Beaches Hotels (43.94 mi)
- Grasonville Hotels (19.53 mi)
- North East Hotels (27.19 mi)
- Rosedale Hotels (24.31 mi)
- Parkville Hotels (27.43 mi)
- Eastern Shore Hotels (40.21 mi)
Most Booked Hotels in Chestertown
- Comfort Inn & Suites Chestertown
- Historic Inns of Annapolis
- Pendry Baltimore
- Hilton Garden Inn Baltimore/White Marsh
- Quality Inn & Suites Bel Air I-95 Exit 77A
- Best Western Plus Hotel & Conference Center
- Hampton Inn Baltimore Bayview Campus
- Annapolis Waterfront Hotel, Autograph Collection
- La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
- La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
- Garner Hotel Glen Burnie BWI Airport Area by IHG
- Americas Best Value Inn Edgewood