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
The price is S$212 per night from 8 Jun to 9 Jun
S$212
8 Jun - 9 Jun
includes taxes & fees
9/10 Wonderful! (1,850 reviews)
"Great hotel..will definitely be back"
Reviewed on 29 May, 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
The price is S$166 per night from 10 Jun to 11 Jun
S$166
10 Jun - 11 Jun
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"This property is old and they are working on improving it; however, we paid a premium price for a good brand that was not up to the standards of its name. We will not be staying there again."
Reviewed on 28 May, 2026
Annapolis Waterfront Hotel, Autograph Collection
80 Compromise St Annapolis MD
Fully refundableReserve now, pay when you stay
The price is S$320 per night from 7 Jun to 8 Jun
S$320
7 Jun - 8 Jun
includes taxes & fees
8.8/10 Excellent! (931 reviews)
"Valet was full had to park garage pretty far away as well as a poor check in experience"
Reviewed on 29 May, 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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