Charlestown Vacations from $332
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Charlestown Vacation
From its rich history to its coastal scenery and beyond, there's loads to love about Charlestown. Discover the wonders of this fascinating city with a Charlestown vacation package that's tailor-made for you. If visiting the sights is a must during your trip to Charlestown, make sure you stop by well-known attractions like Charlestown State Park and Charlestown Family Activities Park. Expedia is here to help you escape your daily routine. Tailor your vacation to Charlestown to suit your travel style, whatever that may be.
The Latest Charlestown vacation packages
Price found within the past 48 hours. Click for updated prices.
Regina's Country Livin'
$332
per person
Dec 11 - Dec 14
found 9 hours ago
Roundtrip flight included
Miami (MIA) to Louisville (SDF)
9.6/10 Exceptional! (14 reviews)
If I am ever doing something between Louisville and Lexington, I will be visiting Regina. This house was well-designed as a true BNB with excellent access/security, thoughtful decor, and an extremely welcoming atmosphere. The reviews praising the breakfast are true - but don't just go for the biscuits and gravy, go for the full experience.
Reviewed on Sep 28, 2026
Pillow and Paddock B&B
$721
per person
Dec 11 - Dec 14
found 6 hours ago
Roundtrip flight included
Miami (MIA) to Louisville (SDF)
10/10 Exceptional! (52 reviews)
Courteous staff and the room was outstanding. It was our second stay at the inn. Everything is first class. We highly recommend it.
Reviewed on Dec 22, 2025
Hyatt Regency Louisville
Downtown Louisville
$525
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Louisville (SDF)
8.8/10 Excellent! (1,004 reviews)
Room was nice and clean. At the same time, both the on site parking garage and the garage elevator were extremely dirty. Especially garage and elevator floors.
Reviewed on Oct 17, 2026
Don't see what you're looking for?
See all available trips from Columbus to Charlestown
View all tripsStay near popular Charlestown attractions
Charlestown Family Activities Park
This family oasis features a splash pad, pirate playground, mini-golf, and roller skating rink in one vibrant location. Enjoy seasonal transformations during "Christmas City" when winter festivities illuminate the park.
Rose Island
Explore the ruins of a 1920s amusement park on this forested island in Charlestown State Park. The 0.9-mile trail reveals stone fountains and swimming pool remnants from this once-vibrant entertainment destination.
Woodford Farms Family Park
This welcoming neighborhood park features playgrounds, basketball, and pickleball courts for active families. Enjoy a relaxed picnic under the shelter or join community events like summer Freeze Pop Fridays.
Charlestown Hotel Deals
Galt House Hotel Trademark Collection by Wyndham
140 North Fourth Street Louisville KY
Fully refundableReserve now, pay when you stay
$140 nightly
$165 total
Nov 8 - Nov 9
Total with taxes and fees
The Brown Hotel
335 W Broadway Louisville KY
Fully refundableReserve now, pay when you stay
$156 nightly
$183 total
Oct 28 - Oct 29
Total with taxes and fees
9.4/10 Exceptional! (1,390 reviews)
"A little run down in the room. It had a musty smell. The most uncomfortable bed I have slept on."
Reviewed on Oct 17, 2026
Radisson Hotel Louisville North
505 Marriott Drive Clarksville IN
Fully refundable
$71 nightly
$81 total
Oct 25 - Oct 26
Total with taxes and fees
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 Charlestown Vacation Packages
Charlestown Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Louisville Intl. Airport (SDF) |
Population | 8,100 |
Max Temp Winter | 40ºF |
Max Temp Summer | 85ºF |
Top Sights | Charlestown State Park, Charlestown Family Activities Park and Deam Lake State Recreation Area |
More vacations you might like
Frequently asked questions
How much does a Charlestown vacation package cost?
Offering excellent value package deals from $332 on Expedia, you'll be surprised at how little a vacation to Charlestown costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Charlestown?
February, July and August are great times to look for cheap Charlestown vacation packages. Opting to travel in less busy periods means you can typically find better prices on flights and hotels.
How many days is enough for Charlestown?
The ideal length for your Charlestown vacation depends on what you'd like to see and do. Typically, a handful of days to a week will give you enough time to visit all the main attractions and discover some hidden treasures along the way.
Is it worth booking a vacation package to Charlestown?
Charlestown is a good vacation destination with attractions like Charlestown State Park among the many things to keep you entertained. Whether you're traveling with the family or planning a trip with friends, a Charlestown vacation promises a good time for everyone.
How to find the best Charlestown package deals?
Bagging a cheap Charlestown package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add a couple of filters and see what's available. You can personalize your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most economical Charlestown package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Charlestown vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component separately. And you'll still get the flexibility to create a customized Charlestown vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Charlestown?
Enjoy fantastic discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Charlestown break.
Does Expedia offer Book Now, Pay Later Charlestown vacation packages?
If you're like us, you love traveling the world but are not a fan of the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Charlestown break over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.
Explore a world of travel with Expedia
- Romantic Hotels in Sellersburg
- Hilton Hotels in Sellersburg
- Scottsburg Hotels
- Rv Parks in Sellersburg
- Cheap Hotels in Charlestown
- Motel 6 Hotels in Charlestown
- Cheap Hotels in Sellersburg
- Memphis Hotels
- 4 Star Hotels in Charlestown
- 4 Star Hotels in Sellersburg
- 3 Star Hotels in Memphis
- Hotels near Charlestown State Park
- Hotels with an Indoor Pool in Charlestown
- Cabin Rentals in Sellersburg
- B&B in Charlestown
- Family Hotels in Sellersburg
- Extended Stay Hotels in Sellersburg
- Jeffersonville Hotels
- Vacation Homes in Memphis
- Motels in Sellersburg
- 5 Star Hotels in Charlestown
- Hotels with an Indoor Pool in Sellersburg
- Pet-Friendly Hotels in Sellersburg
- Charlestown Hotels
- Cabin Rentals in Charlestown
- Motels in Charlestown
- Hotels with a Pool in Sellersburg
- Hotels with Hot Tubs in Charlestown
- Marriott Hotels & Resorts in Sellersburg
- Hotels & Resorts for Couples in Sellersburg
- Clarksville Hotels
- B&B in Sellersburg
- Hotels near Covered Bridge Golf Club
- Resorts & Hotels with Spas in Charlestown
- Hotels with Restaurants in Sellersburg
- Luxury Hotels in Sellersburg
- Sellersburg Hotels
- Red Roof Inn Hotels in Charlestown
- Hilton Hotels in Charlestown
- Extended Stay Hotels in Charlestown
- Pet-Friendly Hotels in Charlestown
- Best Western Hotels in Charlestown
- Madison Hotels
- Cabin Rentals in Memphis
- Cheap Hotels in Jeffersonville - Clarksville
- Villas in Sellersburg
- Red Carpet Inn Hotels in Charlestown
- Henryville Hotels
- New Albany Hotels
- Red Roof Inn Hotels in Sellersburg
- Hotels with Hot Tubs in Sellersburg
- Muscatatuck National Wildlife Refuge
- Park Theatre Civic Center
- Horseshoe Southern Indiana Casino
- Scott County Fairgrounds
- Thomas Family Winery
- Howard Steamboat Museum
- Scottsburg Vacations
- Squire Boone Caverns
- Clifty Falls State Park
- Sunrise Falls Golf Course
- Deam Lake State Recreation Area
- Falls of the Ohio State Park
- Corydon Vacations
- Derby Dinner Playhouse
- Jeffersonville Vacations
- Visit Sellersburg
- Charlestown State Park
- New Albany Vacations
- Corydon Capitol State Historic Site
- Battle of Corydon Memorial Park
- Falls of the Ohio Interpretive State Park
- Turtle Run Winery
- Stream Cliff Herb Farm and Winery
- Wyandotte Cave
- Visit Henryville
- Atlantis Waterpark
- Austin Vacations
- Charlestown Family Activities Park
- Madison Vacations
- Madison Railroad Station Museum
- Marengo Cave National Landmark
- Visit Charlestown
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
