Search for Cheap Deals onHotels in Chester
Check Last Minute Chester Hotel Deals
Choose from 1177 Chester Hotel Deals
Historic Inns of Annapolis
The room really showed its age. The entire room was tilted.... so much so that a bottle rolled on the floor from the left to the right without any push. The bed was likewise tilted and really difficult to sleep comfortably. The elevator was out of order, and there were older guests on the 3rd floor ...
Reviewed on Feb 23, 2026
DoubleTree by Hilton Hotel Annapolis
Food and bar was excellent rooms were clean and average but entire stay quite comfortable
Reviewed on Feb 23, 2026
Graduate by Hilton Annapolis
Friendly, clean
Reviewed on Feb 22, 2026
Crowne Plaza Annapolis by IHG
clean room,
Reviewed on Feb 23, 2026
Hilton Garden Inn Annapolis Downtown
Clean room and excellent staff.
Reviewed on Feb 23, 2026
Annapolis Waterfront Hotel, Autograph Collection
Several years ago this hotel was one of the best in Annapolis...now it's a neglected dump. It's sad!
Reviewed on Feb 18, 2026
Country Inn & Suites by Radisson, Annapolis, MD
Nice large room, clean, and temperature controls worked as expected. Front deck personnel were pleasant. Breakfast was good, with a variety of options.
Reviewed on Feb 21, 2026
Sonesta ES Suites Annapolis
Room was as described. Nice area and friendly staff.
Reviewed on Feb 23, 2026
The Westin Annapolis
Staff was awesome, shout out to Elena for all the help .
Reviewed on Feb 17, 2026
Courtyard by Marriott Annapolis
The room was clean. All the staff was professional and courteous.
Reviewed on Feb 20, 2026
Hyatt Place Kent Narrows & Marina
Great spot
Reviewed on Feb 22, 2026
SpringHill Suites by Marriott Annapolis
Room was clean.
Reviewed on Feb 23, 2026
Find cheap hotels in Chester
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 Chester 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 Chester.
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 Chester’s 1,177 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 $86. 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 Chester 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 Chester. No matter your reason for visiting Chester, 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 Chester 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 Chester for as low as $86.
How many hotels are there in Chester?
With over 1,177 hotels in Chester, 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 $86.
How to find cheap car rentals in Chester?
Finding a cheap car rental deal in Chester is as easy as scoring cheap hotels in Chester. 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 Chesapeake Exploration Center
- Hotels near U.S. Naval Academy
- Hotels near Chesapeake Bay
- Hotels near Chesapeake Bay Bridge
- Hotels near Annapolis City Dock
- Hotels near Sandy Point State Park
- Hotels near Anne Arundel Medical Center
- Hotels near Maryland State House
- Hotels near Westfield Annapolis Mall
- Hotels near Navy-Marine Corps Memorial Stadium
- Hotels near Chesapeake Bay Maritime Museum
- Hotels near St. Michaels Winery
- Hotels near Annapolis Maritime Museum
- Hotels near Annapolis Harbor Center Shopping Center
- Hotels near Maryland Quiet Waters Park
- Hotels near Annapolis Mall Shopping Center
- Hotels near Maryland Hall for Creative Arts
- Hotels near Queenstown Premium Outlets
- Hotels near Queenstown Harbor Golf Club
- Hotels near William Paca House
- Annapolis Hotels
- St. Michaels Hotels
- Easton Hotels
- Glen Burnie Hotels
- Stevensville Hotels
- Chesapeake Beach Hotels
- Eastern Shore Hotels
- Pasadena Hotels
- Grasonville Hotels
- Chestertown Hotels
- Edgewater Hotels
- Severna Park Hotels
- North Beach Hotels
- Essex Hotels
- Rock Hall Hotels
- Tilghman Hotels
- Gambrills Hotels
- Crownsville Hotels
- Centreville Hotels
- Arnold Hotels
