Carefree Vacations from $513

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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.
The Trail Hotel

The Trail Hotel

4 out of 5
Price was $609, price is now $513 per person
$513
per person
Apr 2 - Apr 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
8.6/10 Excellent! (91 reviews)
Staff was very friendly and accommodating. Overall placement are expectations. Food drinks were great, rooms were nice but dark as we had overcast days and not a lot of natural light.

Reviewed on Feb 21, 2026

Derby City Gaming & Hotel - A Churchill Downs Property

Derby City Gaming & Hotel - A Churchill Downs Property

4 out of 5
Save 100% on your flight
Price was $2,758, price is now $2,183 per person
$2,183
per person
Apr 30 - May 3
found 1 day ago
Roundtrip flight included
Houston (IAH) to Louisville (SDF)
9.4/10 Exceptional! (1,606 reviews)
Big comfy and clean Fabulouse staff A special shout out to Chad at the bourbon bar for the wonderful conversation

Reviewed on Feb 20, 2026

Louisville Marriott Downtown

Louisville Marriott Downtown

4 out of 5
Downtown Louisville
Price was $802, price is now $648 per person
$648
per person
Apr 17 - Apr 19
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 Grady

The Grady

4 out of 5
Downtown Louisville
Price was $928, price is now $779 per person
$779
per person
Apr 17 - Apr 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9.4/10 Exceptional! (1,001 reviews)
Clean room. Pleasant employees. No issues, but nothing really stood out. Certainly nothing bad - but nothing exceptional either. I would certainly stay again. The restaurant charge me $10.00 - plus tip - for 2 plain cups of coffee. I'm still thinking about that ... paying $5.00 for a cup of black coffee...

Reviewed on Feb 19, 2026

Greenfield Inn and Suites Elizabethtown, KY I65 Exit 94

Greenfield Inn and Suites Elizabethtown, KY I65 Exit 94

2 out of 5
Price was $702, price is now $592 per person
$592
per person
May 1 - May 3
found 20 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
8.8/10 Excellent! (1,419 reviews)
Property and Room was clean. Breakfast served starting at 5:30 allowed us to get an early start to our day. The food was good and hot. Easy access on and off I65 in Elizabethtown, Ky. There were also a good variety of restaurants within walking distance of the Hotel.

Reviewed on Feb 19, 2026

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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 Mar 4 to Mar 5
$75 total
Mar 4 - Mar 5
Total with taxes and fees
7.6/10 Good! (1,003 reviews)
Staff is very friendly. Water pressure is excellent. Breakfast and coffee provided the next morning.

Reviewed on Feb 19, 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
$103 nightly
The price is $115 total per night from Feb 27 to Feb 28
$115 total
Feb 27 - Feb 28
Total with taxes and fees
8.6/10 Excellent! (371 reviews)
Clean room. Good food.

Reviewed on Feb 15, 2026

Holiday Inn Express Corydon by IHG
Derby Time Riverside Cabin

Derby Time Riverside Cabin

Derby IN
10/10 Exceptional! (142 reviews)
Incredible stay! Gorgeous views, awesome deck, fantastic kitchen setup. The cabin was spotless, super stylish, and every appliance worked perfectly. We loved every minute of our weekend getaway. 10/10!

Reviewed on Feb 23, 2026

Get rates
Derby Time Riverside Cabin
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

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Frequently asked questions

How much does a Carefree vacation package cost?
You can pick up a vacation package to this destination from $513 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.