Charlestown Vacations from $495

Book a Hotel + Flight or Car together to unlock savings

Photo by Mark Wilcoxson

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.
Hancock House

Hancock House

3 out of 5
Downtown Louisville
Price was $650, price is now $495 per person
$495
per person
Feb 12 - Feb 15
found 22 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Louisville (SDF)
8.2/10 Very Good! (245 reviews)
The apartment was so elegant with an antique vibe. It had high ceilings and lots of tall windows with drapes and blackout blinds. Modern stainless steel kitchen appliances. I really liked that it had an icemaker and lamps in every room. Besides the stairs you couldn’t hear the neighbors.The host made things even more convenient by providing late or early check in, late check out or the option to add an extra night right from the confirmation email of your booking. If you like wholesome comfort and simple amenities you would love this charming apartment stay.

Reviewed on Oct 31, 2025

Holiday Inn Express Louisville Airport Expo Center by IHG

Holiday Inn Express Louisville Airport Expo Center by IHG

2.5 out of 5
Hayfield Dundee
Price was $844, price is now $632 per person
$632
per person
Feb 12 - Feb 15
found 22 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Louisville (SDF)
8.6/10 Excellent! (1,001 reviews)
Very nice would stay here again

Reviewed on Nov 30, 2025

Hilton Garden Inn Louisville Downtown

Hilton Garden Inn Louisville Downtown

3.5 out of 5
Downtown Louisville
Price was $738, price is now $565 per person
$565
per person
Feb 12 - Feb 15
found 22 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Louisville (SDF)
8.4/10 Very Good! (1,000 reviews)
Staff was courteous. Great location. Will stay here again.

Reviewed on Dec 2, 2025

Hilton Garden Inn Louisville Mall of St. Matthews

Hilton Garden Inn Louisville Mall of St. Matthews

3 out of 5
St. Matthews
Price was $664, price is now $512 per person
$512
per person
Feb 12 - Feb 15
found 22 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Louisville (SDF)
9.4/10 Exceptional! (835 reviews)
Clean and comfortable room, staff was very courteous.

Reviewed on Dec 1, 2025

Omni Louisville Hotel

Omni Louisville Hotel

4 out of 5
Downtown Louisville
Price was $754, price is now $590 per person
$590
per person
Feb 12 - Feb 15
found 22 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Louisville (SDF)
9.2/10 Wonderful! (1,672 reviews)
Hotel was absolutely gorgeous. Loved the library bar for a night cap. Enjoyed the shopping and made a custom hat at Fleastyle.

Reviewed on Dec 7, 2025

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Discover the most popular places to visit in Charlestown

Charlestown Family Activities Park

Enjoy a fun-filled day at Charlestown Family Activities Park during your trip to Charlestown. Stroll along the riverfront or discover the area's sunrises.

Charlestown Family Activities Park

Charlestown Hotel Deals

Galt House Hotel Trademark Collection by Wyndham

Galt House Hotel Trademark Collection by Wyndham

4 out of 5
140 North Fourth Street Louisville KY
Fully refundableReserve now, pay when you stay
$133 nightly
The price is $157 total per night from Dec 16 to Dec 17
$157 total
Dec 16 - Dec 17
Total with taxes and fees
8.8/10 Excellent! (3,815 reviews)
Everything good

Reviewed on Dec 4, 2025

Galt House Hotel Trademark Collection by Wyndham
Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

3.5 out of 5
830 Phillips Lane Louisville KY
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $103 total per night from Dec 10 to Dec 11
$103 total
Dec 10 - Dec 11
Total with taxes and fees
8.8/10 Excellent! (1,012 reviews)
Room was good.

Reviewed on Dec 3, 2025

Crowne Plaza Louisville Airport Expo Ctr by IHG
Omni Louisville Hotel

Omni Louisville Hotel

4 out of 5
400 S. 2nd Street Louisville KY
Fully refundableReserve now, pay when you stay
$167 nightly
The price is $197 total per night from Jan 1 to Jan 2
$197 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
9.2/10 Wonderful! (1,698 reviews)
Clean Spacious and good atmosphere.

Reviewed on Dec 2, 2025

Omni Louisville Hotel
See all 2,081 properties in Charlestown
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

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Frequently asked questions

How much does a Charlestown vacation package cost?
Offering excellent value package deals from $495 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.

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