Chester Holidays
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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
10/10 Exceptional! (126 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
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (1,886 reviews)
THis is the second time in a row staying here bith times they placed my room on the court yard while I had to listen to loud music form a wedding being heald to late in the evening. AAlso both times our room was not cleaned with new towls etc. When I noticed after 5:00 PM the hotel just asid sorry ...
Reviewed on 9 Feb 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
The price is NZ$156 per night from 22 Feb to 23 Feb
NZ$156
22 Feb - 23 Feb
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
The staff were so nice and helpful and the amenities were great. The restaurant and bar were great especially the breakfast and of course the cookies. The shuttle was so convenient, fast, and super polite. Great stay. I recommend and will stay again next time I'm in town.
Reviewed on 11 Feb 2026
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.
