
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
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
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
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
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
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
Carefree Hotel Deals

Baymont by Wyndham Corydon
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

Holiday Inn Express Corydon by IHG
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

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
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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.



















