Search for Cheap Deals onKid-Friendly Hotels in Chestertown
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Featured Chestertown Family Hotels
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 ...
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 with Pools in Chestertown
Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
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 ...
8.4/10 Very Good! (822 reviews)
"Well received by front desk attendant. Room clean!"
Reviewed on Sep 28, 2025
Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
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 ...
7.2/10 Good! (399 reviews)
"Room temperature was good. Room was also very spacious and clean."
Reviewed on Sep 27, 2025
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 ...
5/10 (174 reviews)
"Rooms are clean, staf was helpful"
Reviewed on Aug 18, 2025
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
- Hotels with Free Parking in Chestertown
- Romantic Hotels in Chestertown
- Pet-friendly Hotels in Chestertown
- Beach Hotels in Chestertown
- Hotels with a Pool 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 River Arts Chestertown
- Hotels near Historical Society of Kent County Maryland
- Hotels near Wilmer Park
- Hotels near Garfield Center for the Arts at the Prince Theater
- Hotels near Crumpton Auction
- Hotels near Sumner Hall
- Hotels near Baltimore Cruise Terminal
- Hotels near U.S. Naval Academy
- Hotels near Ripken Stadium
- Hotels near Chesapeake Bay Bridge
- Hotels near Sandy Point State Park
- Hotels near Annapolis City Dock
- Hotels near Navy-Marine Corps Memorial Stadium
- Hotels near Susquehanna River
- Hotels near White Marsh Mall
- Hotels near Fort McHenry
Cities near Chestertown
- Annapolis Hotels (28.1 mi)
- Dover Hotels (29.45 mi)
- St. Michaels Hotels (30.99 mi)
- Easton Hotels (30.7 mi)
- Aberdeen Hotels (20.7 mi)
- Edgewood Hotels (18.31 mi)
- Delaware Beaches Hotels (43.94 mi)
- Havre De Grace Hotels (22.85 mi)
- Elkton Hotels (29.71 mi)
- Stevensville Hotels (21.06 mi)
- Glen Burnie Hotels (29.99 mi)
- Bel Air Hotels (26.49 mi)
- Middletown Hotels (24.66 mi)
- Grasonville Hotels (19.53 mi)
- White Marsh Hotels (21.43 mi)
- Chesapeake Bay Hotels (117.23 mi)
- Perryville Hotels (23.56 mi)
- North East Hotels (27.19 mi)
- Rock Hall Hotels (10.49 mi)
- Rosedale Hotels (24.31 mi)