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 NZ$616 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
Chester Holiday
Our pick of the best Chester Hotel Deals
Historic Inns of Annapolis
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,881 reviews)
It was a clean room
Reviewed on 8 Nov 2025
Country Inn & Suites by Radisson, Annapolis, MD
2600 Housley Road, Annapolis, MD
Fully refundable
The price is NZ$187 per night from 7 Dec to 8 Dec
NZ$187
7 Dec - 8 Dec
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
Came in late at night and left early the Inn was quiet, safe, comfortable and clean. Ice maker on 1st floor was out of order but there is a second one. Staff was attentive and helpful when we came in and check in was quick and easy. Would stay here again for other local sporting events.
Reviewed on 8 Nov 2025
Sonesta ES Suites Annapolis
170 Admiral Cochrane Dr, Edgewater, MD
Fully refundableReserve now, pay when you stay
The price is NZ$168 per night from 7 Dec to 8 Dec
NZ$168
7 Dec - 8 Dec
includes taxes & fees
8.8/10 Excellent! (940 reviews)
All of the above and more. Spotless room and extraordinary staff!
Reviewed on 8 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.
More holiday ideas
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
