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Featured Chestertown Hotels with a Pool
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 ...
Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
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 ...
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 by Star Rating
More Hotel Options in Chestertown
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- 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 Wilmer Park
- Hotels near Garfield Center for the Arts at the Prince Theater
- Hotels near Crumpton Auction
- 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 White Marsh Mall
- Hotels near Sandy Point State Park
- 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)
- Dover Hotels (29.45 mi)
- St. Michaels Hotels (30.99 mi)
- Havre De Grace Hotels (22.85 mi)
- Delaware Beaches Hotels (43.94 mi)
- Grasonville Hotels (19.53 mi)
- Edgewood Hotels (18.31 mi)
- Perryville Hotels (23.56 mi)
- Aberdeen Hotels (20.7 mi)
- Easton Hotels (30.7 mi)
- Glen Burnie Hotels (29.99 mi)
- Bel Air Hotels (26.49 mi)
- Chesapeake Bay Hotels (117.23 mi)
- White Marsh Hotels (21.43 mi)
- Elkton Hotels (29.71 mi)
- Stevensville Hotels (21.06 mi)
- Galena Hotels (13.19 mi)
- Rosedale Hotels (24.31 mi)
- Eastern Shore Hotels (40.21 mi)
- Appalachian Mountains Hotels (181.58 mi)
Car Rentals Near Chestertown
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- Car rentals in Bel Air
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- Car rentals in White Marsh
- Car rentals in Elkton
- Car rentals in Stevensville
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