
Charles Town Holidays from £617
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Find the right fit
Rest easy
Your Charles Town Holiday
The adventure-packed city of Charles Town is calling. Discover all its secrets with a Charles Town holiday package that's custom made for you. You'll want to sightsee during your trip to Charles Town. Make time for popular attractions like Hollywood Casino at Charles Town Races, Sleepy Hollow Country Club and Bolivar Heights Scenic Overlook. Whoever you're heading away with and whatever your budget, your ultimate Charles Town holiday is just a few clicks away with Expedia.
Top Charles Town Flight + Hotel Deals

The St. Gregory Hotel
Reviewed on 21 Jul 2025


Kellogg Conference Hotel at Gallaudet University
Reviewed on 21 Jul 2025

InterContinental Washington D.C. - The Wharf by IHG
Reviewed on 22 Jul 2025

Global Luxury Suites at The White House
Reviewed on 22 Jul 2025
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, Twin Oaks Tavern Winery and Shepherdstown Museum |
Top hotels in Charles Town

Days Inn by Wyndham Charles Town/Harpers Ferry
Reviewed on 16 Jul 2025

Holiday Inn Express Charles Town by IHG
Reviewed on 14 Jul 2025

Hampton Inn & Suites Charles Town
Reviewed on 20 Jul 2025
Popular places to visit
Sleepy Hollow Country Club
Enjoy a round of golf in Charles Town at Sleepy Hollow Country Club. While in this family-friendly area, find time to visit its casinos.
What to do in Charles Town
Frequently asked questions
More trip options
Expedia's Latest Trends
- Cheap Flights to California
- Cheap Flights to Palestine
- Cheap Flights to Syria
- Cheap Flights to Christmas
- Cheap Flights to Saint Helena Island
- Cheap Flights to Deposit
- Cheap Flights to Transfer
- Cheap Flights to Charleston
- Cheap Flights to Honolulu
- Cheap Flights to Covington
- Cheap Flights to San Jose
- Cheap Flights to Havana
- Cheap Flights to Beach
- Cheap Flights to North Pole
- Cheap Flights to Patagonia
- Cheap Flights to San Diego
* 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.