Chester Holidays
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- Plan, book, travel with confidence
- Better togetherSave up to NZ$616 when you book a flight and hotel together*
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Chester Holiday
Our pick of the best Chester Hotel Deals
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Chester MD
9.8/10 Exceptional! (94 reviews)
Perfect vacation home....large and comfortable.....relaxing, peaceful, close to bike trails, a great homebase for sightseeing many small towns...loved meeting the homeowner, very friendly..
Reviewed on 14 Sept 2025
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
The price is NZ$146 per night from 4 Jan to 5 Jan
NZ$146
4 Jan - 5 Jan 2026
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
did not dine in your hotel.
Reviewed on 24 Dec 2025
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,895 reviews)
Best place to stay is the main building
Reviewed on 22 Dec 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.
