Chester Holidays
Photo by Patricia Knorr
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Top hotels in Chester
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (1,877 reviews)
Such a cool place to stay! Water pressure wasn’t great but it’s a very old building.
Reviewed on 26 Feb, 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
The price is S$122 per night from 3 Mar to 4 Mar
S$122
3 Mar - 4 Mar
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
The staff was very helpful. The room was nice and there were shops & restaurants nearby.
Reviewed on 27 Feb, 2026
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
Fully refundable
The price is S$158 per night from 4 Mar to 5 Mar
S$158
4 Mar - 5 Mar
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
The guy with the bad comb over and poor hair transplant is rude. I handed my id and card and he sat both on the counter if i hand something to you hand it back to me common sense and its respect. This ain't a 5 star hotel and even if it was you don't treat anyone different regardless of ...
Reviewed on 27 Feb, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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