Search for Cheap Deals onHotels in Chestertown
Check Last Minute Chestertown Hotel Deals
Choose from 1088 Chestertown Hotel Deals
Comfort Inn & Suites Chestertown
"Parking clean room"
Reviewed on Jun 5, 2026
Red Roof Inn & Suites Chestertown
"The staff,( if you want to call them that)don't greet you when you walk in to register, I had to initiate the conversation. The elevator floor was filthy nasty and it creaked and groaned. We got off of the elevator on our floor and was greeted by Marijuana smoke and smell. I went back down to inform ..."
Reviewed on Jun 7, 2026
The Lodge at Great Oak Landing
"We left 1 hour after arrival... Enough said! This is very much a buyer beware situation. It's no resort. There was absolutely no food available. Tiki bar is permanently closed. Small restaurant was also closed and our only option was food from the front desk. It's about a 30 minute drive to the closest ..."
Reviewed on Jun 10, 2026
Historic Inns of Annapolis
"The property is in a great location. Plenty to do in the area without having to drive. Unfortunately the staff are less than helpful. We checked out at 11am. At 12 noon, we realized we left a bag hanging from the bathroom door. Called, staff said they wou look into it. Took down my number and address. ..."
Reviewed on Jun 10, 2026
Hampton Inn Baltimore/Glen Burnie
"Never had any problems"
Reviewed on Jun 6, 2026
Pendry Baltimore
"Impeccable! Friendly, fun staff. Stunning location. We were so happy and grateful to be so well cared for."
Reviewed on Jun 8, 2026
Best Western Plus Hotel & Conference Center
"It was a clean ,friendly place , had a bar and prices very reasonable ,the complimentary breakfast was awesome , had a lot more food than other places ,did not have to get out till noon"
Reviewed on Jun 2, 2026
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
"Elevators were down when we stayed. Although originally we were booked a room on the 5th floor, front desk was able to get us a room on the 4th floor…one less flight of stairs to go up and down. With two kids, one being 14 months old, it was a lot to go up and down the stairs. Other than that everything ..."
Reviewed on Jun 9, 2026
Annapolis Waterfront Hotel, Autograph Collection
"Definitely the view of the harbor from our room and how all the stores and restaurants were in walking distance"
Reviewed on Jun 5, 2026
Hilton Garden Inn Baltimore/White Marsh
"Pool was disgusting. Room Smelled like mildew. Too overpriced for the outdated room."
Reviewed on Jun 4, 2026
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
"The room had plenty of space and the room was very clean. Plenty of parking available in th front and the breakfast had a pretty good selection. A couple of the items had to be heated up but a microwave is available."
Reviewed on Jun 11, 2026
Hampton Inn Baltimore/White Marsh
"Good breakfast, room was clean, plenty of places to eat in the area. The bath tub faucet did not entirely shutoff and dripped all night long."
Reviewed on Jun 8, 2026
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 1,088 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 1,088 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 River Arts Chestertown
- Hotels near Rolphs Wharf Marina
- 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 Sumner Hall
- Hotels near U.S. Naval Academy
- Hotels near Chesapeake Bay
- Hotels near Baltimore Cruise Terminal
- Hotels near Annapolis City Dock
- Hotels near Ripken Stadium
- Hotels near Chesapeake Bay Bridge
- Hotels near Sandy Point State Park
- Hotels near Susquehanna River
- Hotels near Fort McHenry
- 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
- Dover Hotels
- St. Michaels Hotels
- Delaware Beaches Hotels
- Aberdeen Hotels
- Easton Hotels
- Perryville Hotels
- Havre De Grace Hotels
- Elkton Hotels
- Glen Burnie Hotels
- Stevensville Hotels
- Edgewood Hotels
- Middletown Hotels
- Bel Air Hotels
- Grasonville Hotels
- North East Hotels
- White Marsh Hotels
- Eastern Shore Hotels
- Rosedale Hotels
- Rock Hall Hotels
