Chester Holidays
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Chester Holiday
Our pick of the best Chester Hotel Deals
Waterfront Sunset Bayview: sleeps 6
Chester MD
10/10 Exceptional! (26 reviews)
We loved our stay at this gorgeous waterfront property in Chester! The home is clean and bright with many gathering spaces for our group of five. We really enjoyed spending time on the back porch on the comfy couches enjoying the beautiful view or sitting around the large dining table eating and ...
Reviewed on 21 Apr 2026
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
The price is NZ$286 per night from 31 May to 1 June
NZ$286
31 May - 1 June
includes taxes & fees
9/10 Wonderful! (1,848 reviews)
A very quaint and historic inn. This was my second stay at the Inns and the staff is very friendly and helpful. Our room was beautiful however, the bathroom needs a little work. Some new caulking and a little elbow grease in the bathtub would help.
Reviewed on 16 May 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.
