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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! (857 reviews)
Excellent hotel. Will stay there anytime I travel to the area.
Reviewed on Nov 26, 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! (418 reviews)
room was clean but the shower curtain was in tatters. multiple rings torn off
Reviewed on Nov 20, 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 (175 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 Crumpton Auction
- Hotels near Historical Society of Kent County Maryland
- Hotels near River Arts Chestertown
- Hotels near Wilmer Park
- 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
- Hotels near Annapolis City Dock
- Hotels near Chesapeake Bay Bridge
- Hotels near Sandy Point State Park
- 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)
- Aberdeen Hotels (20.7 mi)
- Easton Hotels (30.7 mi)
- Elkton Hotels (29.71 mi)
- Perryville Hotels (23.56 mi)
- Edgewood Hotels (18.31 mi)
- Bel Air Hotels (26.49 mi)
- Glen Burnie Hotels (29.99 mi)
- White Marsh Hotels (21.43 mi)
- Middletown Hotels (24.66 mi)
- Stevensville Hotels (21.06 mi)
- Havre De Grace Hotels (22.85 mi)
- Delaware Beaches Hotels (43.94 mi)
- Grasonville Hotels (19.53 mi)
- North East Hotels (27.19 mi)
- Rosedale Hotels (24.31 mi)
- Eastern Shore Hotels (40.21 mi)
- Parkville Hotels (27.43 mi)