
Chester Vacations from $237
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Your Chester Vacation
Reserve a Chester vacation package and get set to experience the best of this city. Consider basing yourself in the neighborhood of Kent Narrows, which is good for cycling, views and nature. If your trip to Chester includes some sightseeing, check out renowned attractions like Chesapeake Bay Environmental Center, Eastern Neck National Wildlife Refuge and Love Point State Park. Stop daydreaming and start doing. Browse the multitude of options on Expedia today and finally put your Chester vacation plans into gear!
The Latest Chester vacation packages


Sofitel Washington DC Lafayette Square
Reviewed on Oct 28, 2025

Hilton Washington DC Capitol Hill
Reviewed on Nov 7, 2025

Kellogg Conference Hotel at Gallaudet University
Reviewed on Nov 4, 2025

Embassy Suites by Hilton Washington D.C. – Convention Center
Reviewed on Nov 9, 2025
Discover the most popular places to visit in Chester
Chesapeake Exploration Center
Learn about the events happening at Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants.
Chester Hotel Deals

Historic Inns of Annapolis
Beautiful
Reviewed on Nov 5, 2025

Country Inn & Suites by Radisson, Annapolis, MD
Came in late at night and left early the Inn was quiet, safe, comfortable and clean. Ice maker on 1st floor was out of order but there is a second one. Staff was attentive and helpful when we came in and check in was quick and easy. Would stay here again for other local sporting events.
Reviewed on Nov 8, 2025

Sonesta ES Suites Annapolis
All of the above and more. Spotless room and extraordinary staff!
Reviewed on Nov 8, 2025
Find the Best Chester Vacation Packages
Chester Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Baltimore Washington Intl. Thurgood Marshall Airport (BWI) |
Population | 4,200 |
Top Sights | Sandy Point State Park, Sandy Point Beach and Matapeake State Park |
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