Chester Holidays from £981
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Your Chester Holiday
Reserve a Chester holiday package and get set to experience the best of this city. Consider basing yourself in the neighbourhood 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 Centre, 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 holiday plans into gear!
Top Chester Flight + Hotel Deals
Kimpton Hotel Monaco Washington DC by IHG
Reviewed on 21 Mar 2026
Sofitel Washington DC Lafayette Square
Reviewed on 28 Mar 2026
Eurostars Saint Gregory Dupont Circle Georgetown
Reviewed on 20 Mar 2026
Landing at Bridge District
Reviewed on 24 Jan 2026
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 |
Top hotels in Chester
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
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
Graduate by Hilton Annapolis
Unique hotel in the heart of Annapolis. The room was lovely, comfortable and well equipped. Parking was a bit expensive $32 one day and strange, couldnt actually park in the covered garrage that was only for vallette patrons. Would have been nice to have a regular coffee maker in the room, only instant ...
Reviewed on 27 Mar 2026
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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. Flight-inclusive packages are ATOL protected.