Charles Town Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Charles Town Vacation

The adventure-packed city of Charles Town is calling. Discover all its secrets with a Charles Town vacation 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 vacation is just a few clicks away with Expedia.

Top Charles Town Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was CA $1,551, price is now CA $1,033 per person
CA $1,033
per person
Jan 31 - Feb 4
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
9/10 Wonderful! (1,285 reviews)

Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Price was CA $1,578, price is now CA $1,053 per person
CA $1,053
per person
Dec 24 - Dec 31
found 12 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Baltimore (BWI)
8.6/10 Excellent! (1,007 reviews)
I really enjoyed my stay at this hotel. It was an easy place to navigate from they had restaurants in a bar on the property. The staff was very kind and I love my room in the space we were in. I would absolutely stay here again.

Reviewed on Nov 11, 2026

Pendry Baltimore

Pendry Baltimore

5 out of 5
Fells Point
Price was CA $3,189, price is now CA $2,187 per person
CA $2,187
per person
Jan 24 - Jan 30
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Baltimore (BWI)
9.4/10 Exceptional! (1,001 reviews)

InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
The Wharf
Save 100% on your flight
Price was CA $2,211, price is now CA $1,527 per person
CA $1,527
per person
Jan 24 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Baltimore (BWI)
9.4/10 Exceptional! (1,229 reviews)
Great hotel and exelent service

Reviewed on Nov 11, 2026

The Potomac Hotel, Autograph Collection

The Potomac Hotel, Autograph Collection

5 out of 5
Southwest
Save 100% on your flight
Price was CA $2,038, price is now CA $1,446 per person
CA $1,446
per person
Jan 31 - Feb 4
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
9.4/10 Exceptional! (1,072 reviews)

Ready to book your vacation to Charles Town?

 

Choose your dates

Charles Town Hotel Deals

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 CA $140 per night from Nov 30 to Dec 1
CA $140
CA $171 total
Nov 30 - Dec 1
includes taxes & fees
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 CA $158 per night from Dec 14 to Dec 15
CA $158
CA $179 total
Dec 14 - Dec 15
includes taxes & fees
Holiday Inn Express Charles Town by IHG
Rodeway Inn & Suites Charles Town

Rodeway Inn & Suites Charles Town

2 out of 5
741 E Washington St Charles Town WV
Fully refundable
The price is CA $96 per night from Dec 14 to Dec 15
CA $96
CA $108 total
Dec 14 - Dec 15
includes taxes & fees
8.6/10 Excellent! (1,009 reviews)
"This hotel has become very run down and not as clean as it used to be. Have been going there for years and have watched it deteriorating over time. Okay for one night but will most likely chose a different place from here on out"

Reviewed on Nov 12, 2026

Rodeway Inn & Suites Charles Town
See all 915 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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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

Frequently asked questions

How much does a Charles Town vacation package cost?
Offering excellent value package deals from CA $1,033 on Expedia, you'll be surprised at how little a vacation to Charles Town costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Charles Town?
December, January and February are great times to search for cheap Charles Town vacation packages. Travelling in less busy periods means you'll typically find lower prices on flights and accommodations.
How many days is enough for Charles Town?
Typically, a handful of days is enough to see the main sights during your Charles Town vacation. However, if you'd like to have some time to unwind or take day trips, consider extending your itinerary.
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 busy. Whether you're travelling 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?
Bagging a cheap Charles Town package deal is a cinch with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, add some filters and see what's available. You can tweak your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Charles Town package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are often lower.
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 tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to see some great airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Charles Town?
If you have your Charles Town travel dates locked in, book as soon as you can to score some terrific deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Charles Town?

  1. Choose when to get away: Check your calendar and pack your bags. Your favourite time of year and the type of activities available will also help you decide when to visit Charles Town.
  2. Figure out your budget: Make sure you have enough money to pay for everything from transportation and food to experiences and flights. Your hotel will probably be the largest expense during your trip to Charles Town.
  3. Decide how long to go for: Now that you're more familiar with Charles Town, you can work out the right length of your vacation. Create a rough plan and give yourself enough time for all the things you want to do.
  4. Bundle your airfare and accommodations: After you've nailed down your travel dates and duration, lock in the ideal Charles Town vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.