Search for Cheap Deals onHotels in Chester
Choose from 1201 Chester Hotel Deals
Historic Inns of Annapolis
"Loved the old style of the property. Dehumidifiers were great to have!"
Reviewed on May 24, 2026
DoubleTree by Hilton Hotel Annapolis
"It was one of the nicest places we've stayed in our travels."
Reviewed on May 22, 2026
Sonesta ES Suites Annapolis
"great"
Reviewed on May 20, 2026
Courtyard by Marriott Annapolis
"A good stay"
Reviewed on May 23, 2026
Crowne Plaza Annapolis by IHG
"Great mid range hotel. The staff was friendly and helpful and the rooms were comfortable and quiet."
Reviewed on May 21, 2026
The Westin Annapolis
"The bar staff and cleaning staff were very kind. The front desk attendants seemed to be unhappy, though I did have one attendant in particular who was very helpful. The hotel rooms themselves were not as nice as most Westins. They were akin to a Hampton Inn which- for the price per night- seems rather ..."
Reviewed on May 19, 2026
Country Inn & Suites by Radisson, Annapolis, MD
"Front desk staff were wonderful in addition to hysterical. Early check in didn’t turn out the way I’d hoped but the room was ready in enough time, thanks to the staff, we were able to get dressed in the room, freshen up and leave on time for a wedding"
Reviewed on May 22, 2026
Graduate by Hilton Annapolis
"The Graduate is an amazing hotel. My favorite part was the attentiveness of the staff, the nostalgic USNA decor, and the greeting of hot chocolate during an unexpected cold and rainy day in May!"
Reviewed on May 23, 2026
Hilton Garden Inn Annapolis Downtown
"Parking is awful! The tiniest cramped parking garage I’ve ever seen. I parked in their lot, paid for parking upon check in and they still somehow gave me a parking citation. When I called the hotel to ask why I received the parking citation they said not to worry about it. Regardless worry about ..."
Reviewed on May 22, 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
Best Western Annapolis
"Great breakfast. Staff was very helpful in answering my questions"
Reviewed on May 21, 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 1,201 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 $96. 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 $96.
How many hotels are there in Chester?
With over 1,201 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 $96.
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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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