Carefree Vacations from $438

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 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 Carefree Vacation

Our vacation packages to Carefree provide countless opportunities to enjoy new sights, sounds and sensations. And with all the travel planning worked out, you'll be free to enjoy your city escape without a care in the world. OBannon Woods State Park, Stephensons General Store and Wyandotte Cave are just a few of the many sights worth exploring during your trip to Carefree. Your perfect Carefree vacation is a couple of clicks away. Browse flights, accommodations and more on Expedia for an adventure that's tailored just for you.

The Latest Carefree vacation packages

Price found within the past 48 hours. Click for updated prices.
Best Western Premier Airport/Expo Center Hotel

Best Western Premier Airport/Expo Center Hotel

3.5 out of 5
Shively
Save 100% on your flight
Price was $598, price is now $438 per person
$438
per person
Mar 25 - Mar 27
found 19 hours ago
Roundtrip flight included
Orlando (MCO) to Louisville (SDF)
8.6/10 Excellent! (959 reviews)
The room was clean and staff were very friendly and helpful, but i do wish the restaurant and bar were open in the evenings.

Reviewed on Jan 5, 2026

Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

3.5 out of 5
Fairgrounds
Price was $827, price is now $585 per person
$585
per person
Apr 21 - Apr 25
found 1 day ago
Roundtrip flight included
Denver (DEN) to Louisville (SDF)
8.8/10 Excellent! (962 reviews)
Todo estuvo perfecto estamos muy contentos

Reviewed on Feb 9, 2026

Louisville Marriott Downtown

Louisville Marriott Downtown

4 out of 5
Downtown Louisville
Save 100% on your flight
Price was $1,307, price is now $940 per person
$940
per person
Apr 21 - Apr 25
found 1 day ago
Roundtrip flight included
Denver (DEN) to Louisville (SDF)
9/10 Wonderful! (1,003 reviews)
Room was spotless. Staff was top notch. Amenities as expected but I did expect a microwave in the room. There wasn't one. 9/10 experience. Will definitely book again!

Reviewed on Jan 16, 2026

The Maple Retreat at Park Mammoth

The Maple Retreat at Park Mammoth

3 out of 5
Save 100% on your flight
Price was $915, price is now $660 per person
$660
per person
Apr 20 - Apr 25
found 17 hours ago
Roundtrip flight included
New York (NYC) to Louisville (SDF)
9.8/10 Exceptional! (13 reviews)
Our cabin was new and updated, cozy. Also, cabin was clean and all amenities were there: laundry machine, dishwasher, utensils, TV's. Purchase your own woods, it will be cheaper. Nice place for getaway.

Reviewed on Apr 12, 2025

Grand Victorian Inn

Grand Victorian Inn

3.5 out of 5
Save 100% on your flight
Price was $655, price is now $493 per person
$493
per person
Apr 20 - Apr 25
found 17 hours ago
Roundtrip flight included
New York (NYC) to Louisville (SDF)
9/10 Wonderful! (698 reviews)
This was like stepping back in time and a breath of fresh air. I frequently tour old victorian homes and museums so when the opportunity arose for us to stay in this Victorian Inn, I was all in! What a beautiful place. I know others find the train disruptive, but we loved it. Didnt hear it past 9pm and we stayed in Suite Joy up front. Need was great, room decorated well, and all around the house. Kitchen area was awesome too. The true highlight of our stay was the staff member who prepared our breakfast. One of the sweetest people I've ever had the pleasure of meeting. Can't wait to come back! Thank you!

Reviewed on Jan 17, 2026

Don't see what you're looking for?
See all available trips from Columbus to Carefree
View all trips

Carefree Hotel Deals

Baymont by Wyndham Corydon

Baymont by Wyndham Corydon

2.5 out of 5
2495 Landmark Avenue NE Corydon IN
Fully refundableReserve now, pay when you stay
$68 nightly
The price is $75 total per night from Feb 22 to Feb 23
$75 total
Feb 22 - Feb 23
Total with taxes and fees
7.4/10 Good! (1,002 reviews)
👍

Reviewed on Feb 3, 2026

Baymont by Wyndham Corydon
Holiday Inn Express Corydon by IHG

Holiday Inn Express Corydon by IHG

2.5 out of 5
249 Federal Drive Nw Corydon IN
Fully refundable
$93 nightly
The price is $103 total per night from Feb 22 to Feb 23
$103 total
Feb 22 - Feb 23
Total with taxes and fees
8.4/10 Very Good! (368 reviews)
The staff and room was great

Reviewed on Feb 3, 2026

Holiday Inn Express Corydon by IHG
Hampton Inn Corydon

Hampton Inn Corydon

2.5 out of 5
2455 Landmark Avenue Corydon IN
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $110 total per night from Feb 20 to Feb 21
$110 total
Feb 20 - Feb 21
Total with taxes and fees
8.8/10 Excellent! (607 reviews)
Availability of laundry room and fitness room were important to me. Many restaurants in walking distance. Superb room. Rapid check in and out. Very accommodating to duration of stay.

Reviewed on Jan 26, 2026

Hampton Inn Corydon
See all 162 properties in Carefree
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 Carefree Vacation Packages

Carefree Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
40ºF
Max Temp Summer
85ºF
Top Sights
Marengo Cave National Landmark, OBannon Woods State Park and Wyandotte Cave

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Carefree vacation package cost?
You can pick up a vacation package to this destination from $438 on Expedia. But how much your vacation to Carefree costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Carefree?
You're likely to find reduced prices and better availability in November, December and January. Take a look at our cheap Carefree vacation packages and you could get some excellent off-season deals.
How many days is enough for Carefree?
Generally, a handful of days is enough to visit the major sights during your Carefree vacation. However, if you prefer to have more time to unwind or go on day tours, think about extending your trip.
How to find the best Carefree package deals?
Start your search for a Carefree package deal by entering your destination and preferred trip dates under our "Packages" tab. Then select some filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Carefree package deal straight away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Carefree getaway off to a flying start.
Is it cheaper to book a Carefree vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll generally snag a better deal than booking each component separately. And you'll still have the freedom to create a customized Carefree vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Carefree?
If you're planning a spur-of-the-moment Carefree vacation, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can find terrific deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Carefree vacation packages?
If you're like us, you love going away 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 help from online lender Affirm, you can spread the cost of your Carefree vacation over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.