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
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 Historical Society of Kent County Maryland and ...
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! (748 reviews)
"It was fine and served our needs."
Reviewed on Mar 3, 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! (335 reviews)
"This property was def. Off season. It was very low key, the room was big and clean, hotel understaffed but I think it was just the time of year. Overall would for sure stay here again.Big value for the cost"
Reviewed on Jan 25, 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 Historical Society of Kent County Maryland and ...
5/10 (167 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 Crumpton Auction
- Hotels near Wilmer Park
- Hotels near Baltimore Cruise Terminal
- Hotels near U.S. Naval Academy
- Hotels near Chesapeake Bay Bridge
- Hotels near Ripken Stadium
- Hotels near Annapolis City Dock
- Hotels near Sandy Point State Park
- Hotels near White Marsh Mall
- Hotels near Fort McHenry
- Hotels near Navy-Marine Corps Memorial Stadium
- Hotels near Susquehanna River
- Hotels near Harford Community College
- 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)
- Grasonville Hotels (19.53 mi)
- Perryville Hotels (23.56 mi)
- Edgewood Hotels (18.31 mi)
- Havre De Grace Hotels (22.85 mi)
- Easton Hotels (30.7 mi)
- Aberdeen Hotels (20.7 mi)
- Bel Air Hotels (26.49 mi)
- Glen Burnie Hotels (29.99 mi)
- Rosedale Hotels (24.31 mi)
- Chesapeake Bay Hotels (117.23 mi)
- Elkton Hotels (29.71 mi)
- Stevensville Hotels (21.06 mi)
- White Marsh Hotels (21.43 mi)
- Eastern Shore Hotels (40.21 mi)
- Middletown Hotels (24.66 mi)
- North East Hotels (27.19 mi)
Car Rentals Near Chestertown
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- Car rentals in Dover
- Car rentals in St. Michaels
- Car rentals in Delaware Beaches
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- Car rentals in Edgewood
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- Car rentals in Aberdeen
- Car rentals in Bel Air
- Car rentals in Glen Burnie
- Car rentals in Rosedale
- Car rentals in Chesapeake Bay
- Car rentals in Elkton
- Car rentals in Stevensville
Top Family Hotel Destinations
- Las Vegas Family Hotels
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- Fort Walton Beach Family Hotels
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- 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
- Quality Inn & Suites Bel Air I-95 Exit 77A
- Hilton Garden Inn Baltimore/White Marsh
- Annapolis Waterfront Hotel, Autograph Collection
- Hampton Inn Baltimore Bayview Campus
- Best Western Plus Hotel & Conference Center
- La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
- La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
- Americas Best Value Inn Edgewood
- Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
- Hampton Inn & Suites Edgewood/Aberdeen-South