Chester Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Patricia Knorr
- Plan, book, travel with confidence
- Better togetherSave up to Rp173.195 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Chester
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,889 reviews)
Every aspect of my stay was excellent. The staff was exceptional.
Reviewed on 14 Nov 2025
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
The price is Rp1.134.579 per night from 25 Nov to 26 Nov
Rp1.134.579
Rp1.293.421 total
25 Nov - 26 Nov
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
Everything
Reviewed on 12 Nov 2025
Graduate by Hilton Annapolis
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
The price is Rp2.363.566 per night from 15 Dec to 16 Dec
Rp2.363.566
Rp2.694.466 total
15 Dec - 16 Dec
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
Nice big rooms, comfortable beds. Well maintained.
Reviewed on 11 Nov 2025
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
