Carefree Vacations from $486

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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.
Best Western Premier Airport/Expo Center Hotel

Best Western Premier Airport/Expo Center Hotel

3.5 out of 5
Shively
Price was $626, price is now $486 per person
$486
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
New York (LGA) 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

Louisville Marriott Downtown

Louisville Marriott Downtown

4 out of 5
Downtown Louisville
Price was $830, price is now $588 per person
$588
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
New York (JFK) 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

Hyatt Regency Louisville

Hyatt Regency Louisville

4 out of 5
Downtown Louisville
Save 100% on your flight
Price was $1,311, price is now $955 per person
$955
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
New York (LGA) to Louisville (SDF)
8.8/10 Excellent! (1,005 reviews)
Delicious Old Fashion. Great location.

Reviewed on Jan 21, 2026

The Duke Hotel

The Duke Hotel

2 out of 5
Downtown Louisville
Price was $661, price is now $501 per person
$501
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
New York (NYC) to Louisville (SDF)
No reviews
Hotel Distil, Autograph Collection

Hotel Distil, Autograph Collection

4 out of 5
Downtown Louisville
Price was $782, price is now $603 per person
$603
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
New York (JFK) to Louisville (SDF)
9.6/10 Exceptional! (422 reviews)
Beautiful room! Clean and the service at the front desk was great! So kind!

Reviewed on Jan 28, 2026

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Carefree Hotel Deals

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
$98 nightly
The price is $109 total per night from Mar 1 to Mar 2
$109 total
Mar 1 - Mar 2
Total with taxes and fees
8.4/10 Very Good! (366 reviews)
As a resident of Harrison County, it’s nice to see that the Holiday Inn is representing our county well. We’ve stayed at this hotel twice now. Both times we’ve rented the Presidential Suite. It’s spacious, great for families or for a date night! Staff has always been super friendly and professional. ...

Reviewed on Jan 12, 2026

Holiday Inn Express Corydon by IHG
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 8 to Feb 9
$75 total
Feb 8 - Feb 9
Total with taxes and fees
7.4/10 Good! (999 reviews)
Very good choice for a road trip break. Especially if you have pets. Appreciated the conveniences of the area, multiple food choices and a Walmart. Gas was a little less than other nearby Hwy 64 exits. Breakfast had waffles, eggs, and sausage plus continental choices. Camera on parking lot made you ...

Reviewed on Jan 4, 2026

Baymont by Wyndham Corydon
Hampton Inn Corydon

Hampton Inn Corydon

2.5 out of 5
2455 Landmark Avenue Corydon IN
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $117 total per night from Feb 6 to Feb 7
$117 total
Feb 6 - Feb 7
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 160 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 $486 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.