Charleston Vacations

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Discover the most popular places to visit in Charleston

Pennyrile Forest State Resort Park

Commune with nature and explore the great outdoors at Pennyrile Forest State Resort Park during your travels in Dawson Springs. Amble around the area's lakeside or visit its temples.

Pennyrile Forest State Resort Park

Charleston Hotel Deals

Days Inn by Wyndham Madisonville

Days Inn by Wyndham Madisonville

2 out of 5
1900 Lantaff Blvd Madisonville KY
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $85 total per night from Dec 14 to Dec 15
$85 total
Dec 14 - Dec 15
Total with taxes and fees
6.8/10 (865 reviews)
the lady that checked me in went out of her way to help me clear up my double booking with the help of the manager that she called. when i checked out, the counter person was prompt in phoning me that i had left some articles and a real shout-out to the lady that cleaned my room to communicate this ...

Reviewed on Dec 1, 2025

Days Inn by Wyndham Madisonville
Comfort Inn & Suites Madisonville

Comfort Inn & Suites Madisonville

2.5 out of 5
545 Powell Dr Madisonville KY
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $103 total per night from Dec 28 to Dec 29
$103 total
Dec 28 - Dec 29
Total with taxes and fees
8.2/10 Very Good! (442 reviews)
Friendly staff, room was clean

Reviewed on Nov 9, 2025

Comfort Inn & Suites Madisonville
Holiday Inn Express & Suites Madisonville by IHG

Holiday Inn Express & Suites Madisonville by IHG

2.5 out of 5
234 Midtown Blvd. Madisonville KY
Fully refundable
$109 nightly
The price is $121 total per night from Dec 21 to Dec 22
$121 total
Dec 21 - Dec 22
Total with taxes and fees
9.2/10 Wonderful! (196 reviews)
Well maintained! Courteous staff. Quick checkin. Spacious room. Modern bath. Best hotel in town!

Reviewed on Nov 14, 2025

Holiday Inn Express & Suites Madisonville by IHG
See all 54 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.

Find the Best Charleston Vacation Packages

Charleston Essential Information

Language
English
Currency
U.S dollars

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Frequently asked questions

How much does a Charleston vacation package cost?
Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a vacation to Charleston costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Charleston?
You can usually find reduced prices and better availability in January, February and April. Browse our cheap Charleston vacation packages and you could land some great off-season deals.
How many days is enough for Charleston?
With a well-organized travel plan, you can easily tick off the most popular Charleston attractions in a few days. But if you want to discover hidden gems or go on day trips, think about booking your Charleston vacation for longer.
How to find the best Charleston package deals?
Use Expedia's filters to help you find some tempting Charleston package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for Charleston package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Charleston vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and stays individually. Better still, you can customize your Charleston trip to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Charleston?
If you're planning a spur-of-the-moment Charleston vacation, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can find awesome deals on your hotels and flights by booking well in advance.
How to plan a trip to Charleston?

  1. Pick the right time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to travel to Charleston.
  2. Set your budget: Factor in expenses like food, flights and transportation when calculating how much to save for your trip to Charleston. Then, choose a hotel that matches your budget, whether that's a wallet-friendly option or a more upscale retreat.
  3. Organize your Charleston escape with Expedia's trip planning tool: Search for and book accommodations and experiences all in one place. You can also collaborate with family and friends to plan an unforgettable trip to Charleston together.
  4. Decide your trip length: Consider how much time you want to spend discovering Charleston. Plan your itinerary so you can get to all the attractions and activities you're interested in at a comfortable pace.
  5. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a customized Charleston vacation package.
  6. Book activities and experiences in advance: Whether it's a ticket to a big attraction or a day trip, you won't have to worry about missing out on Charleston's best offerings. Find all the exciting things to do in Charleston with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Charleston vacation packages?
Secure your dream getaway to Charleston with help from our Book Now, Pay Later vacations. There's no need to scrimp and save or wait until your next paycheck — we've joined forces with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans allow you to spread the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to budget for your trip and snap up cheap deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.