Search for Cheap Deals onHotels in Chester
Choose from 1189 Chester Hotel Deals
DoubleTree by Hilton Hotel Annapolis
"Great staff"
Reviewed on Aug 7, 2026
Historic Inns of Annapolis
"Nice very well location"
Reviewed on Aug 6, 2026
Crowne Plaza Annapolis by IHG
"Nice stay. No complaints."
Reviewed on Aug 7, 2026
Graduate by Hilton Annapolis
St Michaels Inn
"it was ok"
Reviewed on Aug 7, 2026
Annapolis Waterfront Hotel, Autograph Collection
"It was ok, for $300 a night it didn’t seem like it was worth it. The AC broke so we slept in an 80 degree room. But the staff was accommodating and comped us."
Reviewed on Aug 7, 2026
Country Inn & Suites by Radisson, Annapolis, MD
"The air conditioning wasn't working...it completely died the 3rd night. The first 2 nights at least the loud fan was working enough to keep the air circulating. They did offer for us to change rooms on the 3rd night but we had had enough and just wanted to leave. We are in our 70s and my husband ..."
Reviewed on Aug 5, 2026
Hilton Garden Inn Annapolis Downtown
"Good place to stay within walking distance to everything"
Reviewed on Aug 7, 2026
Hyatt Place Kent Narrows & Marina
"Perfect stay in Kent Narrows!!"
Reviewed on Aug 4, 2026
Courtyard by Marriott Annapolis
"I don’t really have anything except just know when breakfast time is so you can plan ahead."
Reviewed on Aug 7, 2026
The Westin Annapolis
"Nice clean hotel rooms very nice comfortable bed, loved the pillows close to everything Miss Shirley’s restaurant was very good food"
Reviewed on Aug 7, 2026
Holiday Inn Express & Suites Annapolis by IHG
"I enjoyed my stay here. The staff was actually very friendly. There was a mishap with the elevator and it was down. The hotel is being maintained but it is dated and a bit shabby. There were stains on the carpets and on the bathroom fixtures. I know the pricing is because of the location but it’s ..."
Reviewed on Aug 8, 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 1,189 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 1,189 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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