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Historic Inns of Annapolis
"Very helpful staff, nice ambiance"
Reviewed on May 18, 2026
DoubleTree by Hilton Hotel Annapolis
Sonesta ES Suites Annapolis
Courtyard by Marriott Annapolis
Crowne Plaza Annapolis by IHG
"Can only get ice on the first floor, no smart tv, and mattress was hard."
Reviewed on May 18, 2026
The Westin Annapolis
"The staff is attentive and the hotel is clean and modern."
Reviewed on May 15, 2026
Country Inn & Suites by Radisson, Annapolis, MD
"Good"
Reviewed on May 18, 2026
Graduate by Hilton Annapolis
"Facilities are old"
Reviewed on May 17, 2026
Hilton Garden Inn Annapolis Downtown
"The hotel is in a good location, walkable to restaurants, nightlife. The room was worn, but clean. The lobby coffee carafe was empty at 7 am on a Sunday morning, very surprising. Did not have time to wait for a new carafe to brew, as Uber was waiting. There was a dog wandering around the lobby, unleashed, ..."
Reviewed on May 17, 2026
Annapolis Waterfront Hotel, Autograph Collection
"It's"
Reviewed on May 18, 2026
Hampton Inn & Suites Annapolis
"Going through renovations, few power issues with kitchenette but other than that fine locationn"
Reviewed on May 18, 2026
Inn at Perry Cabin
"Wonderful location with great views and amenities such as a fire pit"
Reviewed on May 18, 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 1,198 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 $112. 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 $112.
How many hotels are there in Chester?
With over 1,198 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 $112.
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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