Search for Cheap Deals onHotels in Chestertown
Choose from 1095 Chestertown Hotel Deals
Comfort Inn & Suites Chestertown
The Lodge at Great Oak Landing
"Great place to stay. Beautiful area."
Reviewed on Aug 19, 2026
Red Roof Inn & Suites Chestertown
"Hotel, rooms, bathrooms dirty and old. Smelly. Will try another hotel next time"
Reviewed on Aug 20, 2026
Historic Inns of Annapolis
Annapolis Waterfront Hotel, Autograph Collection
"Top notch staff from the front desk, housekeeping and valet. My only real complaint was the early AM construction in the hallway. But all the workers were friendly and courteous to me passing by to get to the elevator."
Reviewed on Aug 20, 2026
Pendry Baltimore
Best Western Plus Hotel & Conference Center
"Breakfast was excellent, pool was fine, hot tub jets didn’t work and I had to bog the front desk to unlock the pool although it was past time for it to be open. Room was fine. I slipped on the bathroom floor going from the shower tub to the sink, since the bathroom was much bigger than the skimpy ..."
Reviewed on Aug 21, 2026
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Quality Inn & Suites Bel Air I-95 Exit 77A
"Room was clean and staff was friendly. Breakfast was good. Close to exit. Felt safe at the location. Parking was easy."
Reviewed on Aug 21, 2026
Hyatt Place Kent Narrows & Marina
"The regular staff was ok. only on the last day of 5 did the maids say hi. after a shower we had some water on the bathroom floor, the white towel was black from the dirt on the floor. they only came once for room service and even then they gave us towels and removed the garbage. they never refilled ..."
Reviewed on Aug 20, 2026
Hampton Inn & Suites Edgewood/Aberdeen-South
Hampton Inn Baltimore/White Marsh
Find cheap hotels in Chestertown
You’re not an average traveler—and Hotwire knows it. Your wanderlust takes you off the beaten path to discover unique adventures and every travel destination’s lesser-known tourist scenes. Hotwire has the hookup! Book your Chestertown hotel with Hotwire to complete your one-of-a-kind travel checklist.
For you, intrepid voyager, Hotwire has a large selection of the best hotels in Chestertown.
Choosing the right hotel in Maryland has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Chestertown’s 1,095 hotels. Choose the one that best catches your trip’s tourist drift.
If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $67. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get great Chestertown hotel deals at the last minute.
While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Chestertown. No matter your reason for visiting Chestertown, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.
Frequently Asked Questions About Chestertown hotels
Where can I find the best last-minute travel deals?
If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can unlock great deals on your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Chestertown for as low as $67.
How many hotels are there in Chestertown?
With over 1,095 hotels in Chestertown, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $67.
How to find cheap car rentals in Chestertown?
Finding a cheap car rental deal in Chestertown is as easy as scoring cheap hotels in Chestertown. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.
- Hotels near Washington College
- Hotels near Garfield Center for the Arts at the Prince Theater
- Hotels near River Arts Chestertown
- Hotels near Rolphs Wharf Marina
- Hotels near Historical Society of Kent County Maryland
- Hotels near Wilmer Park
- Hotels near Crumpton Auction
- Hotels near Sumner Hall
- Hotels near Baltimore Cruise Terminal
- Hotels near U.S. Naval Academy
- Hotels near Sandy Point State Park
- Hotels near Annapolis City Dock
- Hotels near Chesapeake Bay
- Hotels near Ripken Stadium
- Hotels near Chesapeake Bay Bridge
- Hotels near Maryland State House
- Hotels near Navy-Marine Corps Memorial Stadium
- Hotels with Free Parking in Chestertown
- Romantic Hotels in Chestertown
- Family 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
- Oceanfront Hotels in Chestertown
- Hotels with smoking rooms in Chestertown
- Luxury Hotels in Chestertown
- Annapolis Hotels
- St. Michaels Hotels
- Dover Hotels
- Delaware Beaches Hotels
- Perryville Hotels
- Easton Hotels
- Aberdeen Hotels
- Havre De Grace Hotels
- Glen Burnie Hotels
- Stevensville Hotels
- Grasonville Hotels
- Middletown Hotels
- Elkton Hotels
- Edgewood Hotels
- Bel Air Hotels
- North East Hotels
- White Marsh Hotels
- Eastern Shore Hotels
- Rock Hall Hotels
- Pasadena Hotels
