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Choose from 1214 Chester Hotel Deals
DoubleTree by Hilton Hotel Annapolis
"Excellent location, clean and comfortable room. It's our second time staying here and looking forward to returning."
Reviewed on Sep 20, 2026
Historic Inns of Annapolis
"Very nice. Room was unique, due to the restored old building. Large, comfortable. Nicely furnished. Staff were great."
Reviewed on Sep 21, 2026
Crowne Plaza Annapolis by IHG
"Very nice property, toilet needs upgrade."
Reviewed on Sep 19, 2026
Graduate by Hilton Annapolis
St Michaels Inn
"I would say that the motel is a “retro style motel” (don’t let the word “Inn” color your expectations) It is a MOTE. It is not in walking distance to the town, parking is plentiful and the premises are nice, just clean &basic. The stellar part of the stay was the friendly staff and particularly the ..."
Reviewed on Sep 20, 2026
Hilton Garden Inn Annapolis Downtown
"Nice room. Quiet. Helpful staff."
Reviewed on Sep 20, 2026
Sonesta ES Suites Annapolis
"The stay was great. The room had an odd smell but other than that it was good"
Reviewed on Sep 20, 2026
Courtyard by Marriott Annapolis
"Rooms aren’t upgraded, just the facade of the building. It smells like mildew in the room. The air-conditioning is too loud. Looks like unit from the 1990s. It’s a shame that this hotel is charging 400 08 dollars donate for such a pool quality of sleeping. Please refound half of the expanse since ..."
Reviewed on Sep 20, 2026
The Westin Annapolis
"Mieldred at front desk is world class. She should lead this chain. The Chef is not customer friendly and his food sucks. Manager tried her level best but she compromises with some staff there who are screwing it. You should investigate and improve. The valley parking staff are not bad."
Reviewed on Sep 20, 2026
Annapolis Waterfront Hotel, Autograph Collection
"Sadly worst hotel ever in the world. Double booked the room so we caught another couple entering. Elevators often didn’t work. Rubbish would be laying around while front desk staff gossiped the day away. Rooms had faulty or no air con. Ours had temp air con piped through a window …. This simply made ..."
Reviewed on Sep 20, 2026
The Tidewater Inn
"For an older hotel, this venue was very nicely maintained. The staff was wonderful, with the only drawback being the parking situation on the weekends. While normally adequate, there was a large wedding at the hotel while we were there, and all of the parking spaces were taken. Fortunately however, ..."
Reviewed on Sep 20, 2026
Best Western Annapolis
"Good hotel but kinda overpriced"
Reviewed on Sep 20, 2026
Find cheap hotels in Chester
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Frequently Asked Questions About Chester hotels
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