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Choose from 1192 Chester Hotel Deals
DoubleTree by Hilton Hotel Annapolis
Room was ok other than being in the basement, the staff was awesome and friendly
Reviewed on Dec 20, 2025
Historic Inns of Annapolis
Great customer service!
Reviewed on Dec 21, 2025
Crowne Plaza Annapolis by IHG
Spotless room, fantastic pillows and comfortable bed. Keurig coffee machine was a boost! Staff was professional and friendly at check-in and checkout.
Reviewed on Dec 22, 2025
Graduate by Hilton Annapolis
Room was spotless. The staff was helpful
Reviewed on Dec 16, 2025
Hilton Garden Inn Annapolis Downtown
The room was very clean and comfortable, the staff was super friendly in helping make suggestions, i really appreciated their willingness to engage and help
Reviewed on Dec 19, 2025
Country Inn & Suites by Radisson, Annapolis, MD
It was clean, quiet and comfortable. Will definitely come back if in the area again.
Reviewed on Dec 17, 2025
Annapolis Waterfront Hotel, Autograph Collection
Brittnay was very helpful during our check-in.
Reviewed on Dec 13, 2025
Hampton Inn & Suites Annapolis
Loved the option to have a one bedroom suite for the weekend. However, the walls or adjoining door allowed us to hear every word spoken in the room next door.
Reviewed on Dec 14, 2025
The Westin Annapolis
Beautiful and perfect location
Reviewed on Dec 22, 2025
Sonesta ES Suites Annapolis
The room was very clean and everything needed for housekeeping was provided.
Reviewed on Dec 20, 2025
Candlewood Suites Annapolis by IHG
The staff was extremely pleasant and enjoyable to work with!!
Reviewed on Dec 14, 2025
Fairfield Inn & Suites By Marriott Annapolis
Beautiful hotel, clean, very comfortable bed, delicious breakfast. The only negative thing is the $30 parking- not even valet- it’s kind of ridiculous when they have their own dedicated lot. It’s kind of a racket. Everything else was top notch, though!
Reviewed on Dec 21, 2025
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 1,192 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 $85. 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?
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How many hotels are there in Chester?
With over 1,192 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 $85.
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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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