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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 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! (739 reviews)
"No"
Reviewed on Jan 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! (323 reviews)
Nice but no breakfast
"Comfortable room and fair price for the room size. Very clean. Bathroom was nice but had a broken wall mounted hair dryer and the bathroom door did not latch closed so it stayed open about an inch. Front desk was businesslike but not the least bit friendly. There is no breakfast or even coffee offered. ..."
Reviewed on Nov 10, 2024
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 (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 Crumpton Auction
- Hotels near Garfield Center for the Arts at the Prince Theater
- Hotels near Historical Society of Kent County Maryland
- Hotels near Wilmer Park
- Hotels near Baltimore Cruise Terminal
- Hotels near U.S. Naval Academy
- Hotels near Navy-Marine Corps Memorial Stadium
- Hotels near Ripken Stadium
- Hotels near Annapolis City Dock
- Hotels near Chesapeake Bay Bridge
- Hotels near Sandy Point State Park
- Hotels near Susquehanna River
- Hotels near White Marsh Mall
- Hotels near Fort McHenry
- Hotels near Harford Community College
- Hotels near Maryland State House
Cities near Chestertown
- Annapolis Hotels (28.1 mi)
- Dover Hotels (29.45 mi)
- Havre De Grace Hotels (22.85 mi)
- St. Michaels Hotels (30.99 mi)
- Edgewood Hotels (18.31 mi)
- Grasonville Hotels (19.53 mi)
- Perryville Hotels (23.56 mi)
- Aberdeen Hotels (20.7 mi)
- Delaware Beaches Hotels (43.94 mi)
- Glen Burnie Hotels (29.99 mi)
- Easton Hotels (30.7 mi)
- Bel Air Hotels (26.49 mi)
- White Marsh Hotels (21.43 mi)
- Elkton Hotels (29.71 mi)
- Appalachian Mountains Hotels (181.58 mi)
- Middletown Hotels (24.66 mi)
- Stevensville Hotels (21.06 mi)
- Rosedale Hotels (24.31 mi)
- Chesapeake Bay Hotels (117.23 mi)
- North East Hotels (27.19 mi)
Car Rentals Near Chestertown
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- Car rentals in Dover
- Car rentals in Havre De Grace
- Car rentals in St. Michaels
- Car rentals in Edgewood
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- Car rentals in Perryville
- Car rentals in Aberdeen
- Car rentals in Delaware Beaches
- Car rentals in Glen Burnie
- Car rentals in Easton
- Car rentals in Bel Air
- Car rentals in White Marsh
- Car rentals in Elkton
- Car rentals in Appalachian Mountains
- Car rentals in Middletown
Top Family Hotel Destinations
- Las Vegas Family Hotels
- Arcade Family Hotels
- Branson Family Hotels
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- 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
- Sagamore Pendry Baltimore
- Best Western Plus Hotel & Conference Center
- Quality Inn & Suites Bel Air I-95 Exit 77A
- Historic Inns of Annapolis
- La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
- La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
- La Quinta Inn & Suites by Wyndham Baltimore S. Glen Burnie
- Hampton Inn Baltimore Bayview Campus
- Fairfield Inn & Suites by Marriott White Marsh
- Hilton Garden Inn Baltimore/White Marsh
- La Quinta Inn & Suites by Wyndham Aberdeen-APG
- Americas Best Value Inn Edgewood