Name: Historic Inns of Annapolis
Price range: AU$232
Rating: 9

Photo by Patricia Knorr

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Your Chester Holiday

When a city getaway is calling, answer it with a holiday package to Chester. The neighbourhood of Kent Narrows, which is good for cycling, views and nature, makes a great base for your adventures. You'll want to do a little exploring during your trip to Chester. Drop by popular attractions like Chesapeake Bay Environmental Centre, Eastern Neck National Wildlife Refuge and Matapeake State Park. Check out Expedia's extensive range of travel options and start planning your perfect holiday to Chester today.

Chester Holiday

Chester Essential Information

Language	English
Currency	U.S dollars
Closest Airport	Baltimore Washington Intl. Thurgood Marshall Airport (BWI)
Population	4,200
Max Temp Winter	7ºC
Max Temp Summer	27ºC
Top Sights	Sandy Point State Park, Sandy Point Beach and Matapeake State Park

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

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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

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Historic Inns of Annapolis

58 State Circle Annapolis MD

Fully refundableReserve now, pay when you stay

AU$232

31 May - 1 June

includes taxes & fees

9/10 Wonderful! (1,837 reviews)

"This was a beautiful historic hotel directly across from the state capitol building. We had excellent service and the valet parking was fast and friendly. Highly recommend this place!"

Reviewed on 22 May 2026

See all 1,201 properties in Chester

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.