Charleston Vacations from $279

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Your Charleston Vacation

Reserve a Charleston vacation package and you can focus on what matters — enjoying yourself. This means no more planning stresses, just more free time to experience the best parts of this fascinating city, such as its rich history and cultural experiences. If sightseeing is on your list of things to do during your trip to Charleston, find your way to major attractions like Eastern Illinois University. Expedia is here to help you escape your routine. Tailor your vacation to Charleston to suit your travel style, whatever that may be.

The Latest Charleston vacation packages

Price found within the past 48 hours. Click for updated prices.
Staybridge Suites O'Fallon Chesterfield by IHG

Staybridge Suites O'Fallon Chesterfield by IHG

3 out of 5
Price was $380, price is now $279 per person
$279
per person
Oct 2 - Oct 5
found 11 hours ago
Roundtrip flight included
Denver (DEN) to St. Louis (STL)
8.4/10 Very Good! (371 reviews)
Very nice and helpful staff all the time

Reviewed on Aug 7, 2025

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
Price was $768, price is now $407 per person
$407
per person
Oct 2 - Oct 5
found 11 hours ago
Roundtrip flight included
Denver (DEN) to St. Louis (STL)
9.2/10 Wonderful! (1,562 reviews)
Always comfortable, always convenient and reliable when I'm visiting the area. It's my go-to hotel in the area.

Reviewed on Aug 25, 2025

Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield

3 out of 5
Save 100% on your flight
Price was $396, price is now $279 per person
$279
per person
Oct 2 - Oct 5
found 11 hours ago
Roundtrip flight included
Denver (DEN) to St. Louis (STL)
8.2/10 Very Good! (763 reviews)
I booked online and paid via the app. When I arrived on site they explained they had overbooked and had no rooms available. The staff was amazing and went above and beyond and secured a room at another location. Thank you to the staff for taking care of us.

Reviewed on Jul 26, 2025

The Cheshire

The Cheshire

4 out of 5
Save 100% on your flight
Price was $527, price is now $381 per person
$381
per person
Oct 22 - Oct 25
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
8.6/10 Excellent! (1,006 reviews)
The Cheshire kept well from of old! We felt back in to the ages yet very 21C amenities. The location is perfect to explore St. Louis. We'd like to come back!

Reviewed on Aug 23, 2025

DoubleTree by Hilton Hotel St. Louis - Chesterfield

DoubleTree by Hilton Hotel St. Louis - Chesterfield

4 out of 5
Save 100% on your flight
Price was $484, price is now $352 per person
$352
per person
Oct 2 - Oct 5
found 11 hours ago
Roundtrip flight included
Denver (DEN) to St. Louis (STL)
8.6/10 Excellent! (1,000 reviews)
Beautiful property, pleasant and responsive staff, delicious warm cookies! And convenient location near city hall and police department.

Reviewed on Jul 27, 2025

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Charleston Hotel Deals

Unique Suites Hotel

Unique Suites Hotel

2.5 out of 5
920 W Lincoln Ave, Charleston, IL
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $118 total per night from Sep 11 to Sep 12
$118 total
Sep 11 - Sep 12
Total with taxes and fees
Unique Suites Hotel
Days Inn by Wyndham Charleston

Days Inn by Wyndham Charleston

2 out of 5
810 West Lincoln Avenue, Charleston, IL
Fully refundableReserve now, pay when you stay
$82 nightly
The price is $91 total per night from Aug 31 to Sep 1
$91 total
Aug 31 - Sep 1
Total with taxes and fees
Days Inn by Wyndham Charleston
A frame getaway on the Embarrass River in Charleston, Illinois

A frame getaway on the Embarrass River in Charleston, Illinois

2 out of 5
Charleston
Get rates
A frame getaway on the Embarrass River in Charleston, Illinois
See all 83 properties in Charleston
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.

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Frequently asked questions

How much does a Charleston vacation package cost?
You can grab a vacation package to this top destination from $279 on Expedia. However, how much your vacation to Charleston costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Charleston?
If you're looking to book a cheap Charleston vacation package, consider visiting in January, February and September. You'll generally find better prices on airfares and hotels during these months — ideal for a budget-friendly break.
How many days is enough for Charleston?
Usually, a handful of days is enough to go to the main sights during your Charleston vacation. But if you prefer to have some time to rest or take day trips, think about extending your itinerary.
How to find the best Charleston package deals?
Start your search for a Charleston package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Guest rating," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Charleston package deal right away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Charleston escape underway.
Is it cheaper to book a Charleston vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll typically score a better deal than booking each component individually. And you'll still enjoy the freedom to create a personalized Charleston vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Charleston?
If you're considering a spur-of-the-moment Charleston adventure, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can find amazing deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Charleston vacation packages?
Secure your dream escape to Charleston with help from our Book Now, Pay Later vacations. No need to save like crazy or wait until your next payday — we've teamed up with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans mean you can spread the total cost over 3, 6 or 12 months. With no hidden charges or late payment fees, it's easy to stay on budget and snag great deals before they disappear.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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