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Choose from 1189 Chester Hotel Deals
Historic Inns of Annapolis
"Small bathroom and toilet"
Reviewed on Jun 8, 2026
DoubleTree by Hilton Hotel Annapolis
"Staff was great After traveling for 8 hours we were able to check in early and relax"
Reviewed on Jun 7, 2026
Crowne Plaza Annapolis by IHG
"Great place to stay for a short visit to Annapolis."
Reviewed on Jun 4, 2026
Graduate by Hilton Annapolis
"It was a great place to stay."
Reviewed on Jun 7, 2026
Hilton Garden Inn Annapolis Downtown
"Day and Evening front desk staff were friendly, courteous and helpful. The room itself as well as the general condition of the hotel, luggage carts, ice dispensers, carpet condition, especially in room were torn, worn and in need of repair or replacement. The bathroom has peeling wall paper, the ..."
Reviewed on Jun 6, 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
Courtyard by Marriott Annapolis
"Bed was lumpy and room smelled Like stale cigarettes and marijuana filled the second floor. Kept the balcony door open for fresh air that made it difficult to sleep because of feeling unsafe. The staff were friendly at check in and check out. We only needed one night. Will definitely use a different ..."
Reviewed on Jun 2, 2026
Country Inn & Suites by Radisson, Annapolis, MD
"Hot tub was nice, but room reeked of smoke"
Reviewed on Jun 8, 2026
The Westin Annapolis
"Good location, nice hotel"
Reviewed on Jun 1, 2026
St Michaels Inn
"This was a nice, tidy and simple option close to St. Michaels. Not fancy, but nice with everything you need including a summer pool."
Reviewed on Jun 8, 2026
Hampton Inn & Suites Annapolis
"Pool was closed. I was charged for parking that I was unaware of. Ridiculous as this hotel is stand alone and not in a major city. That was surprising. Hotel is run down. Lots of damage. The one chair in the room was broke. Staff was nice."
Reviewed on Jun 8, 2026
Sonesta ES Suites Annapolis
"The staff is the best part of staying here!! They are very helpful. Making you feel at home away from home!!"
Reviewed on Jun 7, 2026
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 1,189 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 $110. 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 $110.
How many hotels are there in Chester?
With over 1,189 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 $110.
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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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