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
Holiday Inn Express Charles Town by IHG
681 Flowing Springs Rd Charles Town WV
Fully refundable
AU$207
31 Aug - 1 Sept
includes taxes & fees
9.2/10 Wonderful! (1,012 reviews)
"Great location, easy check in, and friendly staff They have the cheapest security deposit l have ever seen."
Reviewed on 24 Aug 2026
The Inn at Charles Town - Hollywood Casino
100 Hollywood Dr Charles Town WV
Fully refundableReserve now, pay when you stay
AU$170
26 Aug - 27 Aug
includes taxes & fees
Rodeway Inn & Suites Charles Town
741 E Washington St Charles Town WV
Fully refundable
AU$121
2 Sept - 3 Sept
includes taxes & fees
8.6/10 Excellent! (1,013 reviews)
"The motel had a nice bar and slot machines. The staff was very professional."
Reviewed on 24 Aug 2026
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.
Stay near popular Charles Town attractions
Jefferson County Courthouse
8.2/10 (30 reviews)
After visiting Jefferson County Courthouse, make a plan to see the other sights and activities in Charles Town. While in this family-friendly area, find time to visit its casinos.
Hollywood Casino at Charles Town Races
8.6/10 (678 reviews)
Why not roll the dice with a visit to Hollywood Casino at Charles Town Races during your time in Charles Town? While in this family-friendly area, find time to visit its casinos.
Charles Town Library
7.8/10 (36 reviews)
This historic library, established in 1927, houses both literary treasures and the Jefferson County Museum. Browse the diverse collection or explore local history in the appointment-only Perry Room.
Old Opera House
8.2/10 (27 reviews)
This historic theatre hosts Broadway-style musicals, plays, and concerts in an intimate setting. Arrive early to enjoy the cultural cornerstone of Charles Town before the curtain rises on your evening performance.
Gibson-Todd House
8.2/10 (16 reviews)
This striking red brick residence, built in 1891, features a three-story conical tower and intricate brickwork. Photograph the architectural details while exploring Charles Town's historic district.
Locust Hill Golf Course
8.0/10 (21 reviews)
This scenic 18-hole course challenges golfers with water hazards on 11 holes amid Blue Ridge Mountain views. Reserve your tee time seven days in advance to experience this well-rated West Virginia golf destination.
Zion Episcopal Church Cemetery
8.8/10 (25 reviews)
Step back in time and learn more about local history with a stop at Zion Episcopal Church Cemetery in Charles Town. While you're in the area, find time to visit its casinos.
Beall Air
7.6/10 (14 reviews)
This historic Washington family estate features a striking Ionic portico and stepped gable ends. Explore its significant role in John Brown's 1859 raid while admiring the early 19th-century architectural design.
What to do in Charles Town
Frequently asked questions
How much does a Charles Town holiday package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a holiday to Charles Town costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Charles Town?
You can generally find lower rates and better availability in December, January and February. Explore our cheap Charles Town holiday packages and you could land some great off-season discounts.
How many days is enough for Charles Town?
The ideal length for your Charles Town holiday depends on what you'd like to see. Usually, a few days to a week will give you time to visit all the top attractions and explore some hidden spots along the way.
Is it worth booking a holiday package to Charles Town?
Charles Town is a good holiday destination with attractions like Hollywood Casino at Charles Town Races among the many things to keep you entertained. Whether you're heading away with the family or planning a trip with friends, a Charles Town holiday promises fun for everyone.
How to find the best Charles Town package deals?
Use Expedia's filter tool to find some tempting Charles Town package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or browse for Charles Town package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your holiday package as early as possible.
Is it cheaper to book a Charles Town holiday as a package?
You can enjoy significant savings on your next Charles Town break by booking a customised holiday package. Check the "Package" heading, then enter your destination and travel dates to see the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Charles Town?
If you're planning an impromptu Charles Town trip, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land amazing deals on your flights and hotels by booking ahead.
How to plan a trip to Charles Town?
- Pick your dates: What you plan to do in Charles Town and your preferred season will help you decide when to get away.
- Budget wisely: In addition to the price of your accommodation, you'll need to factor in other expenses too. These include food, transportation and flights. Also, put aside a little extra for unexpected costs that could crop up during your trip to Charles Town.
- Decide how long to go for: Now that you know more about Charles Town, you can figure out the ideal length of your break. Put together a rough plan and give yourself enough time to get through everything on your must-do list.
- Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to find a Charles Town holiday package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
