Chester Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Patricia Knorr
- Plan, book, travel with confidence
Better together
Save up to NZ$616 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, 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! (1,853 reviews)
"Good"
Reviewed on 25 Sept 2025
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is NZ$209 per night from 30 Sept to 1 Oct
NZ$209
30 Sept - 1 Oct
includes taxes & fees
8.6/10 Excellent! (1,015 reviews)
McMullen Symposium
"Clean room, efficient staff and superb breakfast. Grateful thanks to the hotel staff."
Reviewed on 21 Sept 2025
Country Inn & Suites by Radisson, Annapolis, MD
2600 Housley Road, Annapolis, MD
Fully refundable
The price is NZ$200 per night from 14 Oct to 15 Oct
NZ$200
14 Oct - 15 Oct
includes taxes & fees
9/10 Wonderful! (1,022 reviews)
"This was a convenient property for visiting the Naval Academy and historic Annapolis. The property seemed to be well taken care of. The breakfast was the usual breakfast area with a waffle maker, oatmeal, a hot serving dish of an egg product, a meat, and a potato product. Nothing fancy. The room ..."
Reviewed on 22 Sept 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.
