Search for Cheap Deals onHotels in Chester
Check Last Minute Chester Hotel Deals
Choose from 1190 Chester Hotel Deals
Graduate by Hilton Annapolis
The hotel has cute and trendy decor. It’s located centrally nearby many restaurants and coffee shops around. Our room was clean and spacious. Check in was easy and on point. We had no issues with this hotel. This is my second Graduate hotel that I’m staying in and they are very efficient.
Reviewed on Mar 16, 2026
Crowne Plaza Annapolis by IHG
Clean room
Reviewed on Mar 16, 2026
Historic Inns of Annapolis
The elevator was not working the entire time.
Reviewed on Mar 13, 2026
Hilton Garden Inn Annapolis Downtown
The man working the front desk when I arrived was very friendly and helpful. He is a great part of your team. I only regret that I do not remember his name.
Reviewed on Mar 15, 2026
DoubleTree by Hilton Hotel Annapolis
Friendly staff
Reviewed on Mar 17, 2026
Sonesta ES Suites Annapolis
I have stayed here twice and this is a really great hotel to stay at. They also have breakfast which is great too.
Reviewed on Mar 16, 2026
Country Inn & Suites by Radisson, Annapolis, MD
outstanding customer service and business support! give everyone a raise!!
Reviewed on Mar 13, 2026
Courtyard by Marriott Annapolis
The room was clean and well stocked with towels. I liked being able to walk outside to the patio. On addition, having a restaurantwith good food on-site is great!
Reviewed on Mar 8, 2026
Annapolis Waterfront Hotel, Autograph Collection
Great waterfront room with roomy balcony. Gym was nice also. Can't wait for the var and restaurants to open.
Reviewed on Mar 15, 2026
The Westin Annapolis
Clean Room, quiet nights sleep in comfortable bed. Shower was awesome (Water Pressure A+). Friendly staff, and bar staff at night were very friendly and accommodating.
Reviewed on Mar 15, 2026
SpringHill Suites by Marriott Annapolis
We were surprised to find out upon our arrival that parking was not included in our stay. Apparently the lot is owned by an outside entity. Our room was fairly clean and comfortable. The breakfast left a lot to be desired.
Reviewed on Mar 14, 2026
Best Western Kent Narrows Inn
The first room had not been cleaned... The second room's heater did not work. We finally got into a decent room on the third try. The pool was murky. I didn't even let my kids go in the hot tub because it smelled so weird. The sauna was luke warm. The breakfast was good, and the staff were trying ...
Reviewed on Mar 15, 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 1,190 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 $104. 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 $104.
How many hotels are there in Chester?
With over 1,190 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 $104.
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 Annapolis City Dock
- Hotels near Chesapeake Bay Bridge
- Hotels near Westfield Annapolis Mall
- Hotels near Sandy Point State Park
- Hotels near Maryland State House
- Hotels near Navy-Marine Corps Memorial Stadium
- Hotels near Anne Arundel Medical Center
- Hotels near Annapolis Mall Shopping Center
- 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 Maryland Hall for Creative Arts
- Hotels near Queenstown Harbor Golf Club
- Hotels near William Paca House
- Hotels near Avalon Theatre
- Annapolis Hotels
- St. Michaels Hotels
- Easton Hotels
- Glen Burnie Hotels
- Stevensville Hotels
- Chesapeake Beach Hotels
- Eastern Shore Hotels
- Pasadena Hotels
- Grasonville Hotels
- Chestertown Hotels
- Severna Park Hotels
- Essex Hotels
- North Beach Hotels
- Edgewater Hotels
- Rock Hall Hotels
- Tilghman Hotels
- Gambrills Hotels
- Millersville Hotels
- Centreville Hotels
- Crownsville Hotels
