Carefree Vacations from $562

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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 $773, price is now $562 per person
$562
per person
Feb 28 - Mar 5
found 4 hours ago
Roundtrip flight included
Boston (BOS) 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
Save 100% on your flight
Price was $1,260, price is now $816 per person
$816
per person
Feb 28 - Mar 5
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9/10 Wonderful! (1,003 reviews)
Very nice hotel. Great stay!

Reviewed on Dec 6, 2025

Hotel Distil, Autograph Collection

Hotel Distil, Autograph Collection

4 out of 5
Downtown Louisville
Save 100% on your flight
Price was $1,209, price is now $845 per person
$845
per person
Feb 28 - Mar 5
found 2 hours ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9.6/10 Exceptional! (422 reviews)
Clean, well appointed, convenient to restaurants and downtown Louisville.

Reviewed on Jan 3, 2026

The Grady

The Grady

4 out of 5
Downtown Louisville
Price was $948, price is now $689 per person
$689
per person
Mar 13 - Mar 17
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9.4/10 Exceptional! (1,001 reviews)
Breakfast, lunch & dinner amazing I’m Vegan they accommodated meals for me at the Swan Restaurant/Bar down stairs

Reviewed on Jan 5, 2026

Homewood Suites by Hilton Louisville Downtown, KY

Homewood Suites by Hilton Louisville Downtown, KY

3 out of 5
Downtown Louisville
Price was $915, price is now $666 per person
$666
per person
Mar 13 - Mar 17
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9.2/10 Wonderful! (1,004 reviews)
Room was clean. Staffs were friendly.

Reviewed on Jan 4, 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
$66 nightly
The price is $74 total per night from Jan 17 to Jan 18
$74 total
Jan 17 - Jan 18
Total with taxes and fees
7.4/10 Good! (1,003 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
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
$87 nightly
The price is $97 total per night from Jan 11 to Jan 12
$97 total
Jan 11 - Jan 12
Total with taxes and fees
8.4/10 Very Good! (363 reviews)
The staff was very friendly and helpful with all we needed. The rooms were clean and breakfast was good. We stayed at this location specifically for the pool, however the hot tub was low on water, not filtering and murky & gross. That was a huge disappointment

Reviewed on Jan 4, 2026

Holiday Inn Express Corydon by IHG
Derby Time Riverside Cabin

Derby Time Riverside Cabin

Derby IN
10/10 Exceptional! (135 reviews)
Perfect spot on Ohio River with access to lots of trails. Cabin clean and scenic views.

Reviewed on Jan 1, 2026

Get rates
Derby Time Riverside Cabin
See all 161 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 $562 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.