Charles Town Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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Top hotels in Charles Town

Days Inn by Wyndham Charles Town/Harpers Ferry
Days Inn by Wyndham Charles Town/Harpers Ferry
2 out of 5
642 E Washington Street, Charles Town, WV
Fully refundableReserve now, pay when you stay
The price is S$95 per night from 4 Aug to 5 Aug
S$95
4 Aug - 5 Aug
includes taxes & fees
8/10 Very Good! (1,002 reviews)
"Very much appreciated the free shuttle service to the casino. All the staff were friendly and helpful."

Reviewed on 4 Jul, 2025

Days Inn by Wyndham Charles Town/Harpers Ferry
Hampton Inn & Suites Charles Town
Hampton Inn & Suites Charles Town
2.5 out of 5
157 Pimlico Dr, Charles Town, WV
Fully refundableReserve now, pay when you stay
The price is S$194 per night from 16 Jul to 17 Jul
S$194
16 Jul - 17 Jul
includes taxes & fees
9.4/10 Exceptional! (1,004 reviews)
"Everything was perfect!"

Reviewed on 6 Jul, 2025

Hampton Inn & Suites 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 S$155 per night from 4 Aug to 5 Aug
S$155
4 Aug - 5 Aug
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
I'll stay again
"Awesome! Clean, great complimentary breakfast!"

Reviewed on 6 Jul, 2025

Holiday Inn Express Charles Town by IHG
See all 878 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.

What to do in Charles Town

Exclusive Virginia Wine Country Day Trip Tour

Exclusive Virginia Wine Country Day Trip Tour

S$641
per traveller
Exclusive Virginia Wine Country Day Trip 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.