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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! (772 reviews)
"Great hotel in a great community…. Easily accessible to anything nearby."
Reviewed on Jun 15, 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! (367 reviews)
"Great chain. The only issue is floors are not very clean. If you can't steam-wash carpets often best not to have them. Bathroom floor is sticky. But room is large and comfortable, staff very pleasant."
Reviewed on Jun 16, 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 (171 reviews)
"Mrs Mae is very friendly and helpful. Checks on you to make sure everything is ok. I’d recommend it - stayed 3 weeks for work. Loved my little room!! Mrs Mae was a bonus!!"
Reviewed on May 24, 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 Historical Society of Kent County Maryland
- Hotels near Wilmer Park
- Hotels near River Arts Chestertown
- 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 Annapolis City Dock
- Hotels near Sandy Point State Park
- Hotels near Ripken Stadium
- Hotels near Chesapeake Bay Bridge
- Hotels near Navy-Marine Corps Memorial Stadium
- Hotels near Susquehanna River
- Hotels near White Marsh Mall
- Hotels near Cedar Lane Regional Park
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)
- Edgewood Hotels (18.31 mi)
- Perryville Hotels (23.56 mi)
- Havre De Grace Hotels (22.85 mi)
- Bel Air Hotels (26.49 mi)
- Elkton Hotels (29.71 mi)
- Glen Burnie Hotels (29.99 mi)
- Chesapeake Bay Hotels (117.23 mi)
- Grasonville Hotels (19.53 mi)
- Stevensville Hotels (21.06 mi)
- White Marsh Hotels (21.43 mi)
- Middletown Hotels (24.66 mi)
- North East Hotels (27.19 mi)
- Eastern Shore Hotels (40.21 mi)
- Rock Hall Hotels (10.49 mi)
Car Rentals Near Chestertown
- Car rentals in Annapolis
- Car rentals in Dover
- Car rentals in St. Michaels
- Car rentals in Delaware Beaches
- Car rentals in Easton
- Car rentals in Aberdeen
- Car rentals in Edgewood
- Car rentals in Perryville
- Car rentals in Havre De Grace
- Car rentals in Bel Air
- Car rentals in Elkton
- Car rentals in Glen Burnie
- Car rentals in Chesapeake Bay
- Car rentals in Grasonville
- Car rentals in Stevensville
- Car rentals in White Marsh
Top Family Hotel Destinations
- Las Vegas Family Hotels
- Arcade Family Hotels
- Branson Family Hotels
- Biloxi Family Hotels
- Ocean City Family Hotels
- Orlando Family Hotels
- Buffalo Family Hotels
- Reno Family Hotels
- Colorado Springs Family Hotels
- Phoenix Family Hotels
- Niagara Falls Family Hotels
- New York Family Hotels
- Whistler Family Hotels
- Houston Family Hotels
- Fort Walton Beach Family Hotels
- Pensacola Beach Family Hotels
- Tampa Family Hotels
- Myrtle Beach Family Hotels
- Miami Beach Family Hotels
- Birmingham Family Hotels
Top Booked Hotels in Chestertown
- Comfort Inn & Suites Chestertown
- Historic Inns of Annapolis
- Sagamore Pendry Baltimore
- La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
- Hilton Garden Inn Baltimore/White Marsh
- Quality Inn & Suites Bel Air I-95 Exit 77A
- La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
- Hampton Inn Baltimore/Glen Burnie
- Best Western Plus Hotel & Conference Center
- Hampton Inn Baltimore/White Marsh
- Annapolis Waterfront Hotel, Autograph Collection
- La Quinta Inn & Suites by Wyndham Baltimore S. Glen Burnie