Charles Town Holidays
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Your Charles Town Holiday
When you choose a Charles Town holiday package, you can really enjoy your escape to the fullest. Delve into the best things about this fascinating city knowing that everything has been looked after before you go. Fill your days with visits to Hollywood Casino at Charles Town Races, Sleepy Hollow Country Club and Bolivar Heights Scenic Overlook, some of the things you shouldn't miss during your trip to Charles Town. A few quick clicks is all it takes to create your dream Charles Town holiday on Expedia.
Charles Town Holiday
Charles Town Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Hagerstown Regional Airport (HGR) |
Population | 5,900 |
Max Temp Winter | 4ºC |
Max Temp Summer | 29ºC |
Top Sights | Bolivar Heights Scenic Overlook, Old Opera House and Twin Oaks Tavern Winery |
Our pick of the best Charles Town Hotel Deals
The Inn at Charles Town - Hollywood Casino
"Clean room"
Reviewed on 1 June 2026
Holiday Inn Express Charles Town by IHG
"Great, leisurely breakfast. Quiet hallways, courteous front desk."
Reviewed on 9 June 2026
Hillbrook Inn
"We had an amazing long weekend at Hillbrook. It was like being transported to an English Countryside. The Winter Cottage where we stayed was so comfortable and charming. Their chefs are absolutely amazing, we are still talking about how good our breakfasts and the tasting dinner was."
Reviewed on 26 May 2026
Discover the most popular places to visit in Charles Town
Beall Air
You can find out about the history of Charles Town with a stop at Beall Air. While you're in the area, find time to visit its casinos.
Gibson-Todd House
You can find out about the history of Charles Town with a trip to Gibson-Todd House. While in this family-friendly area, find time to visit its casinos.
