Photo by Patricia Knorr
Plan, book, travel with confidence
Better together
Save up to NZ$545 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
Our pick of the best Chester Hotel Deals
Crowne Plaza Annapolis, an IHG Hotel
173 Jennifer Rd, Annapolis, MD
Fully refundable
The price is NZ$250 per night from 6 Jun to 7 Jun
NZ$250
per night
6 Jun - 7 Jun
8.6/10 Excellent! (1,005 reviews)
"Property was great. But for the price a complementry breakfast would have been nice."
Reviewed on 27 May 2024
Historic Inns of Annapolis
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is NZ$283 per night from 16 Jun to 17 Jun
NZ$283
per night
16 Jun - 17 Jun
8.8/10 Excellent! (1,614 reviews)
"Absolutely love these properties and the so-rounding area! Great places to eat and shop all within walking distance."
Reviewed on 27 May 2024
Graduate Annapolis
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is NZ$362 per night from 9 Jun to 10 Jun
NZ$362
per night
9 Jun - 10 Jun
9.2/10 Wonderful! (1,035 reviews)
"Spacious rooms"
Reviewed on 28 May 2024
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.
Frequently asked questions
Discover the most popular places to visit in Chester
Chesapeake Exploration Center
Learn about the events happening in Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants.
What to do in Chester
Chesapeake Region Wine Tour
NZ$277
Per adult
More holiday ideas
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.