Search for Cheap Deals onHotels in Chester
Choose from 1188 Chester Hotel Deals
Historic Inns of Annapolis
"We really enjoyed our stay, especially because of the convenient location and great amenities. When we experienced issues with the cable and shower, the staff promptly moved us to another room without causing any major inconvenience. My partner and I would absolutely stay here again."
Reviewed on Jun 28, 2026
DoubleTree by Hilton Hotel Annapolis
"Loved me room. Very nice hotel. I will stay there again when in the area!"
Reviewed on Jun 28, 2026
Crowne Plaza Annapolis by IHG
"Overall the hotel and my room was awesome. I was on the side of the highway. A little noisy but it was tolerable"
Reviewed on Jun 28, 2026
Annapolis Waterfront Hotel, Autograph Collection
"When we arrived people were still checking out because of the problem with the elevators. So we have to wait for the room to be cleaned. We booked a handicap room but was giving a standard room I called down to the desk and they did move us to a handicap room. The Restaurant was closed for remodeling. ..."
Reviewed on Jun 17, 2026
Graduate by Hilton Annapolis
"Convenient location. Beautiful property. Friendly staff!"
Reviewed on Jun 27, 2026
Country Inn & Suites by Radisson, Annapolis, MD
"This hotel was fine for our one-night stopover in Annapolis. Location was good with plenty of free parking. The room was spacious, although fairly basic. Beds were clean and comfortable. On the down side, the foyer of the hotel wasn't very clean when we visited. Perhaps someone had just been in with ..."
Reviewed on Jun 24, 2026
Hilton Garden Inn Annapolis Downtown
"Great stay in a prime location!!"
Reviewed on Jun 24, 2026
The Westin Annapolis
"Ed frames broken, heavenly bed experience was compromised. This was the worst Westin hotel I have ever experienced"
Reviewed on Jun 16, 2026
Courtyard by Marriott Annapolis
"Property was clean , staff very accommodating. Would stay here again."
Reviewed on Jun 27, 2026
St Michaels Inn
"Lovely staff interactions and a perfect two-night stay for us. I suggest you plan to drive to town as it’s not close by. Parking lots are easy to get to and are free in town."
Reviewed on Jun 27, 2026
Best Western Kent Narrows Inn
"Gentleman who checked me in was super-friendly and the room was clean and well maintained. Very good value. Low cost. High quality"
Reviewed on Jun 25, 2026
Best Western Annapolis
"From the very helpful reception staff to the clean and cool room, it was an ideal room for us on this trip."
Reviewed on Jun 26, 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 1,188 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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How many hotels are there in Chester?
With over 1,188 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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