Search for Cheap Deals onHotels in Chester
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Choose from 1210 Chester Hotel Deals
Historic Inns of Annapolis
Crowne Plaza Annapolis by IHG
Sonesta ES Suites Annapolis
"Great"
Reviewed on Nov 4, 2026
DoubleTree by Hilton Hotel Annapolis
Graduate by Hilton Annapolis
"Nice size rooms. Convenient location. Logan at the front desk was super helpful. Lady in coffee shop not helpful and coffee was very bitter. Overall a good choice."
Reviewed on Nov 3, 2026
Annapolis Waterfront Hotel, Autograph Collection
Hilton Garden Inn Annapolis Downtown
"Shower did not work. Shower drain flooded bathroom floor. Sink didn’t drain, and room not made up or towels refreshed as they were used to mop up the flooded floor. Not exactly Hilton Honors standards."
Reviewed on Nov 4, 2026
Country Inn & Suites by Radisson, Annapolis, MD
"A once-nice property but quite run down. Carpets need cleaning or replacing. Duct tape on the carpet in my room (425). Hallway carpets not vacuumed, lot of waste on them."
Reviewed on Nov 4, 2026
Best Western Annapolis
St Michaels Inn
"Check-in staff gave us a handicap room which was not necessary. Walked in the room and the toilet was filthy! When I told the staff they gave us a room which was not required they stated we asked for it. This was not true. Also stated they didn’t have time to clean the room. Gave us another room ..."
Reviewed on Nov 1, 2026
Courtyard by Marriott Annapolis
"It took over one hour to check in at 1 o'clock in the morning. After traveling for 15 hours, One is very tired at that hour.. three days prior and each consecutive day thereafter, I called to confirm that we would be arriving at midnight, and they said everything would be OK. When we got to the hotel, ..."
Reviewed on Nov 4, 2026
The Westin Annapolis
Find cheap hotels in Chester
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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 1,210 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 $77. 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 $77.
How many hotels are there in Chester?
With over 1,210 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 $77.
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.
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