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Featured Chestertown Family Hotels
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 ...
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 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! (752 reviews)
"clean and comfy"
Reviewed on Mar 31, 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! (339 reviews)
"I loved the decor of my room. The king size bed was cozy."
Reviewed on Mar 22, 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 (168 reviews)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
Reviewed on Oct 16, 2024
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 Garfield Center for the Arts at the Prince Theater
- Hotels near Wilmer Park
- Hotels near Crumpton Auction
- Hotels near Baltimore Cruise Terminal
- Hotels near U.S. Naval Academy
- Hotels near Ripken Stadium
- Hotels near Chesapeake Bay Bridge
- Hotels near Annapolis City Dock
- Hotels near Sandy Point State Park
- Hotels near White Marsh Mall
- Hotels near Navy-Marine Corps Memorial Stadium
- Hotels near Susquehanna River
- Hotels near Fort McHenry
- Hotels near Harford Community College
- Hotels near Cedar Lane Regional Park
Cities near Chestertown
- Annapolis Hotels (28.1 mi)
- St. Michaels Hotels (30.99 mi)
- Dover Hotels (29.45 mi)
- Delaware Beaches Hotels (43.94 mi)
- Perryville Hotels (23.56 mi)
- Havre De Grace Hotels (22.85 mi)
- Grasonville Hotels (19.53 mi)
- Easton Hotels (30.7 mi)
- Edgewood Hotels (18.31 mi)
- Aberdeen Hotels (20.7 mi)
- Glen Burnie Hotels (29.99 mi)
- Bel Air Hotels (26.49 mi)
- Stevensville Hotels (21.06 mi)
- Chesapeake Bay Hotels (117.23 mi)
- Elkton Hotels (29.71 mi)
- Eastern Shore Hotels (40.21 mi)
- White Marsh Hotels (21.43 mi)
- Middletown Hotels (24.66 mi)
- Rosedale Hotels (24.31 mi)
- North East Hotels (27.19 mi)
Car Rentals Near Chestertown
- Car rentals in Annapolis
- Car rentals in St. Michaels
- Car rentals in Dover
- Car rentals in Delaware Beaches
- Car rentals in Perryville
- Car rentals in Havre De Grace
- Car rentals in Grasonville
- Car rentals in Easton
- Car rentals in Edgewood
- Car rentals in Aberdeen
- Car rentals in Glen Burnie
- Car rentals in Bel Air
- Car rentals in Stevensville
- Car rentals in Chesapeake Bay
- Car rentals in Elkton
- Car rentals in Eastern Shore
Top Family Hotel Destinations
- Las Vegas Family Hotels
- Arcade Family Hotels
- Branson Family Hotels
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- Ocean City Family Hotels
- Orlando Family Hotels
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- 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
- La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
- Sagamore Pendry Baltimore
- Quality Inn & Suites Bel Air I-95 Exit 77A
- Annapolis Waterfront Hotel, Autograph Collection
- Hampton Inn Baltimore Bayview Campus
- Best Western Plus Hotel & Conference Center
- Hilton Garden Inn Baltimore/White Marsh
- La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
- Fairfield Inn & Suites by Marriott White Marsh
- La Quinta Inn & Suites by Wyndham Aberdeen-APG
- Country Inn & Suites by Radisson, Baltimore North, MD