Chester Packages (Flight + Hotel)
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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 ฿3,764 per night from 8 Jun to 9 Jun
฿3,764
฿5,403 total
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 ฿3,738 per night from 31 May to 1 Jun
฿3,738
฿4,261 total
31 May - 1 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 ฿9,069 per night from 16 Jun to 17 Jun
฿9,069
฿10,338 total
16 Jun - 17 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.
What to do in Chester
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
