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

Hillbrook Inn

Hillbrook Inn

4 out of 5
4490 Summit Point Road Charles Town WV
The price is AU$260 per night from 20 July to 21 July
AU$260
20 July - 21 July
includes taxes & fees
8.6/10 Excellent! (683 reviews)
"The door to the room was stuck and the bottom was rotting, the door looked like it was about to break. The covers had stains, we slept on top of the covers because we were worried about their cleanliness. The shower had pink bacteria on the door and corners. The window in the shower had big white ..."

Reviewed on 8 July 2026

Hillbrook Inn
The Inn at Charles Town - Hollywood Casino

The Inn at Charles Town - Hollywood Casino

3 out of 5
100 Hollywood Dr Charles Town WV
Fully refundableReserve now, pay when you stay
The price is AU$200 per night from 13 July to 14 July
AU$200
13 July - 14 July
includes taxes & fees
8.6/10 Excellent! (591 reviews)
"It was clean and the staff was helpful. A shuttle bus is available to take you to the casino and back to the hotel every 20 minutes. That was very convenient."

Reviewed on 6 July 2026

The Inn at Charles Town - Hollywood Casino
Holiday Inn Express Charles Town by IHG

Holiday Inn Express Charles Town by IHG

2.5 out of 5
681 Flowing Springs Rd Charles Town WV
Fully refundable
The price is AU$161 per night from 26 July to 27 July
AU$161
26 July - 27 July
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
"The breakfast is not that good , did not eat it the second day was out of things around 9:15 did not get replenished supposed to be over at 10:00 am."

Reviewed on 8 July 2026

Holiday Inn Express Charles Town by IHG
See all 922 properties in Charles Town
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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.
See properties

What to do in Charles Town

Exclusive Virginia Wine Country Day Trip Tour

Private Virginia Wine Country Tour

AU$720
per traveller
Private Virginia Wine Country Tour
See all activities 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?

  1. Pick your dates: What you plan to do in Charles Town and your preferred season will help you decide when to get away.
  2. 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.
  3. 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.
  4. 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.

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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.