Search for Cheap Deals onHotels in Chester
Choose from 1198 Chester Hotel Deals
Historic Inns of Annapolis
"My beef is with cancelation. I had to unexpectedly travel out of the country for a death on the family. So I called to let the hotel I was not coming and asked for a refund, after some discussion the hotel agreed not to charge. A couple days later I got an invoice copy from you guys, telling how ..."
Reviewed on Aug 28, 2026
Crowne Plaza Annapolis by IHG
"Large room"
Reviewed on Aug 28, 2026
DoubleTree by Hilton Hotel Annapolis
"My check-in went smoothly. I had a young lady assist me, and she was absolutely amazing! She was so sweet, funny, and welcoming. She was even kind enough to offer me two cookies and a bottle of water when I arrived at my room. I believe her name tag said Ms. Betty. She had beautiful red and orange ..."
Reviewed on Aug 27, 2026
Country Inn & Suites by Radisson, Annapolis, MD
Sonesta ES Suites Annapolis
"Spacious rooms, very good breakfast selection, even had tacos for breakfast!"
Reviewed on Aug 26, 2026
St Michaels Inn
"The rooms, though dated, are clean. I did bring to the attention of the manager that the towel bar in my bathroom was coming off. The handrail to walk down the steps into the pool was also loose, which I think is a safety hazard. The manager acknowledged he knew about it, but despite tons of cosmetic ..."
Reviewed on Aug 28, 2026
Graduate by Hilton Annapolis
Annapolis Waterfront Hotel, Autograph Collection
"Air conditioning did not work at the hotel, ended up having to leave and stay somewhere else for the night. Kept giving us the run around. They did comp the room for one night but should have been compensated for the inconvenience. Rooms were 90 degrees! Beautiful hotel, great location."
Reviewed on Aug 28, 2026
Hilton Garden Inn Annapolis Downtown
"Reception staff are very helpful, hassle free check in and out process.Good dining options within walking distance and very close to the marina and downtown area."
Reviewed on Aug 28, 2026
The Westin Annapolis
"Walking distance from the historic main street."
Reviewed on Aug 26, 2026
Courtyard by Marriott Annapolis
"Just ok"
Reviewed on Aug 24, 2026
Hampton Inn & Suites Annapolis
"Womack Rd, Annapolis, Maryland Hampton Inn Room 121 was not up to par with Hampton Inn standards. Bathroom door had no door knob. Just hole in door. Carpet was suspect. Room had “below average hotel room” smell. Owner is at the top and IS responsible for these items. Not necessarily Hampton Inn! ..."
Reviewed on Aug 28, 2026
Find cheap hotels in Chester
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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 $104. 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.
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Frequently Asked Questions About Chester hotels
Where can I find the best last-minute travel deals?
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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 $104.
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