Charles Town Holidays from £773
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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
Price found within the past 48 hours. Click for updated prices.
The River Inn
Northwest
£773
per person
7 Dec - 14 Dec
found 1 day ago
Return direct flight included
London (LGW) to Baltimore (BWI)
9.4/10 Exceptional! (2,106 reviews)
Was greeted with an early check-in, which worked out perfectly since I arrived in D.C. early. The kitchenette in the room is great for anyone on a budget, with a Trader Joe’s just a 5-minute walk away. Be sure to scan the QR code in the room to see what extra amenities are available; I didn’t realize they had dish drying racks until I scanned it!
The walls are a bit on the thin side, so light sleepers might get woken up. During my first two nights, a loud group on my floor woke me around 1:00 AM, though I didn't hear them for the rest of my stay. The A/C unit can also be noisy, but I got used to it pretty quickly.
Overall, very good stay for my 5 day trip.
Reviewed on 20 Sept 2026
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
The Inn at Charles Town - Hollywood Casino
100 Hollywood Dr Charles Town WV
Fully refundableReserve now, pay when you stay
£97
22 Sept - 23 Sept
includes taxes & fees
8.6/10 Excellent! (632 reviews)
"The room was nice, except for the chair arms was filthy stains in the chair very nasty"
Reviewed on 20 Sept 2026
Holiday Inn Express Charles Town by IHG
681 Flowing Springs Rd Charles Town WV
Fully refundable
£84
19 Oct - 20 Oct
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
"Loved the shuttle to and from the Casino!"
Reviewed on 20 Sept 2026
Rodeway Inn & Suites Charles Town
741 E Washington St Charles Town WV
Fully refundable
£65
29 Sept - 30 Sept
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"Awesome bar. Friendly staff. One of a kind!"
Reviewed on 21 Sept 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.
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.
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.
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.
Frequently asked questions
Why should I book my Charles Town holiday with Expedia?
With exceptional-value airfares, hotel and car hire options all in one place, Expedia makes planning your Charles Town getaway a piece of cake. Moreover, we can help you bundle your bookings into a package holiday so you can save even more. Pick from wonderful stays, add your flights and/or a hire car (and maybe also some exciting activities!) and get incredible prices. Need to change plans? Expedia has a flexible cancellation policy for many bookings. To find out more, check out our Customer Service Portal link.
When is the best time of year to holiday in Charles Town?
If you love the buzz of peak season, visit Charles Town in April, August and October. Travelling during the quieter months of November, December and January will help you skip the crowds. To get an idea of what type of weather to expect, the average daytime temperature in January, the coolest time of year in Charles Town, is 0ºC. The warmest month here is July, when temperatures reach an average of 24ºC.
What is the top hotel for my holiday in Charles Town?
Put your feet up and relax in comfort in Charles Town by choosing Euro Suites Hotel as your home-away-from-home and gateway to exploration and adventure.
How do I get a cheap holiday to Charles Town?
Find flights that fit your schedule, add a hotel to your booking and see how much you save with a Charles Town holiday. It's that simple! From hotels and flights to hire cars and tours, Expedia makes travelling cheap and easy. And with more than 400 airlines and 321,000 properties across the globe to select from, you won't be short of choice. Learn more about how you can save money on your holiday when you combine your flight and hotel bookings with Expedia.
What should I do on my Charles Town holiday?
With must-visit attractions such as Hollywood Casino at Charles Town Races and Harpers Ferry National Historical Park, a holiday in Charles Town is full of exciting things to do and see. Summit Point Motorsports Park and Appalachian Trail Conservancy Headquarters are a couple of other sights worth discovering.
What is the best area to stay in when on holiday in Charles Town?
If you'll be visiting Hollywood Casino at Charles Town Races, maximise your time sightseeing and book a stay nearby. It's one of the best attractions in Charles Town.
Do I need a visa for my Charles Town holiday?
Official government websites have all the information you need on visa requirements, application procedures and any necessary documentation. Your nationality and purpose for visiting, whether it be for tourism or business, will determine if you'll need a visa for Charles Town. Also be sure that your passport is up to date and has at least six months validity remaining after the date of your return. Do all your travel planning ahead of time to avoid any nasty last-minute surprises.
What should I wear on my Charles Town holiday?
Though everyone's personal style is different, it can be useful to have some guidelines for what type of clothes to wear on your holiday in Charles Town. We recommend searching style blogs before leaving for inspiration on local dress codes or fashion trends. Pack with confidence by looking up the local weather conditions in Charles Town. July brings the warmest temperatures, with daytime averages of 24ºC, while January days average 0ºC, making it the coolest month.
What does an Expedia Charles Town holiday include?
Hotels, flights and a reliable car for all your road trip adventures. Simply choose your favourite bundle and get access to incredible deals. Once you've made your booking, add on some tours and activities and watch your savings stack up. When it comes to planning your Charles Town break, you're the one in control! Private holiday homes and apartments are a couple of the most popular property types in Charles Town. No matter your preference or size of your group, you can rely on Expedia for the freedom to personalise your next dream escape.
Does Expedia offer Book Now, Pay Later Charles Town holidays?
Your bank balance shouldn't get in the way of taking a holiday, so Expedia has devised a solution to help. Now that we've joined forces with online lender Klarna, it's easier than ever to book a fantastic getaway without using up all your savings. Klarna offers flexible payment options during the checkout process that take the worry out of budgeting for your escape. Consider one of these flexible payment options:
- Pay monthly holidays: Realise your holiday dreams sooner with Klarna's convenient instalment plans. If paying across multiple instalments sounds right for you, pick this option at checkout.
- No-deposit holidays: Clicking the "book now" button is easier with this option. With no deposit required for your holiday, you can Book Now, Pay Later and start working on your travel plans.
Can I choose my airline with a Charles Town Expedia holiday?
Yes, you sure can. Expedia has access to more than 400 airline partners globally, so go with the carrier that best fits your budget needs.
Explore a world of travel with Expedia
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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.
