Carefree Vacations from $577

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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 Grady

The Grady

4 out of 5
Downtown Louisville
Price was $710, price is now $577 per person
$577
per person
May 10 - May 13
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) 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

Hyatt Regency Louisville

Hyatt Regency Louisville

4 out of 5
Downtown Louisville
Price was $885, price is now $670 per person
$670
per person
May 10 - May 13
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Louisville (SDF)
8.8/10 Excellent! (1,005 reviews)
Very clean room, the staff was friendly as well. Looking forward to our stay again next year.

Reviewed on Feb 7, 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

Stellar Suites

Stellar Suites

4.5 out of 5
Downtown Louisville
Save 100% on your flight
Price was $9,237, price is now $7,750 per person
$7,750
per person
Apr 30 - May 3
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Louisville (SDF)
9.6/10 Exceptional! (113 reviews)
Great location. Clean and awesome communication.

Reviewed on Feb 19, 2026

Candlewood Suites Louisville North by IHG

Candlewood Suites Louisville North by IHG

2.5 out of 5
Price was $830, price is now $708 per person
$708
per person
Apr 9 - Apr 13
found 24 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Louisville (SDF)
8.4/10 Very Good! (396 reviews)
Luckily booked the room on the road 15 minutes before arrival. Upon arrival, discovered it was the only room available. The room was clean and spacious. The staff we encountered were friendly and helpful. Overall nice place.

Reviewed on Feb 14, 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
$70 nightly
The price is $77 total per night from Mar 4 to Mar 5
$77 total
Mar 4 - Mar 5
Total with taxes and fees
7.4/10 Good! (1,001 reviews)
This hotel is one of my go to’s when I’m in the area which is usually once a month for the last year or so. The rooms are always clean, staff is friendly, it’s quiet (even though there’s a busy road & highway near by) beds are comfortable, pillows are soft, breakfast is always really good. Everything ...

Reviewed on Feb 16, 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
8.4/10 Very Good! (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! (140 reviews)
The host was very welcoming and accommodating. There was an impending snow storm and they allowed me to check in at 8 a.m. instead of the usual 4 p.m. We are very interested in staying here again

Reviewed on Feb 10, 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 $577 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.