Charles Town Trips (flight + hotel)

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Top hotels in Charles Town

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 P6,441 per night from Jul 7 to Jul 8
P6,441
P7,278 total
Jul 7 - Jul 8
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"The customer service was excellent."

Reviewed on Jun 28, 2026

Holiday Inn Express Charles Town by IHG
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 P7,176 per night from Jul 6 to Jul 7
P7,176
P8,651 total
Jul 6 - Jul 7
includes taxes & fees
8.6/10 Excellent! (588 reviews)
"Stayed the night to see a concert. The shuttle was very convenient, the staff was friendly and the room was clean and comfortable."

Reviewed on Jun 21, 2026

The Inn at Charles Town - Hollywood Casino
Hillbrook Inn

Hillbrook Inn

4 out of 5
4490 Summit Point Road Charles Town WV
The price is P9,115 per night from Jul 13 to Jul 14
P9,115
P11,738 total
Jul 13 - Jul 14
includes taxes & fees
8.6/10 Excellent! (679 reviews)
"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 May 26, 2026

Hillbrook Inn
See all 921 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.

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

P30,275
per traveler
Private Virginia Wine Country Tour
See all activities in Charles Town

Frequently asked questions

How much does a Charles Town vacation package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a vacation 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 vacation 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 vacation 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 vacation package to Charles Town?
Charles Town is a good vacation 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 vacation 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 vacation package as early as possible.
Is it cheaper to book a Charles Town vacation as a package?
You can enjoy significant savings on your next Charles Town break by booking a customized vacation 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 vacation 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 accommodations, 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 vacation 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.