
Carefree Vacations from $253
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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.

Hancock House
Downtown Louisville
Save 100% on your flight
Price was $383, price is now $253 per person
$253
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Louisville (SDF)
8.2/10 Very Good! (245 reviews)
The apartment was so elegant with an antique vibe. It had high ceilings and lots of tall windows with drapes and blackout blinds. Modern stainless steel kitchen appliances. I really liked that it had an icemaker and lamps in every room. Besides the stairs you couldn’t hear the neighbors.The host made things even more convenient by providing late or early check in, late check out or the option to add an extra night right from the confirmation email of your booking. If you like wholesome comfort and simple amenities you would love this charming apartment stay.
Reviewed on Oct 31, 2025

Crowne Plaza Louisville Airport Expo Ctr by IHG
Fairgrounds
Save 100% on your flight
Price was $778, price is now $466 per person
$466
per person
Jan 23 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
8.8/10 Excellent! (962 reviews)
Clean cozy room & great hotel amenities but the TV had no channels at all
Reviewed on Dec 2, 2025

Holiday Inn Louisville Airport South by IHG
Save 100% on your flight
Price was $780, price is now $472 per person
$472
per person
Jan 23 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
8.8/10 Excellent! (765 reviews)
I've always had good luck with holiday inn. I have never encountered a dirty location. Rooms were comfortable, staff was friendly and breakfast was delicious. What more could you ask for? Oh, the location was a definite plus!
Reviewed on Nov 30, 2025

Galt House Hotel Trademark Collection by Wyndham
Downtown Louisville
Save 100% on your flight
Price was $1,115, price is now $736 per person
$736
per person
Jan 23 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
9/10 Wonderful! (3,770 reviews)
Friendly staff & it was decorated nicely for Christmas
Reviewed on Dec 3, 2025

Santas Lodge and Resort
Price was $724, price is now $482 per person
$482
per person
Jan 23 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
8/10 Very Good! (277 reviews)
Cute place! Decorated for Christmas and Christmas music playing. Made me want to work there!
Reviewed on Nov 23, 2025
Carefree Hotel Deals

Baymont by Wyndham Corydon
2495 Landmark Avenue NE Corydon IN
Fully refundableReserve now, pay when you stay
$60 nightly
The price is $67 total per night from Jan 4 to Jan 5
$67 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
7.4/10 Good! (1,011 reviews)
Always a great place to stay for the price.
Reviewed on Nov 29, 2025

Hampton Inn Corydon
2455 Landmark Avenue Corydon IN
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $115 total per night from Dec 11 to Dec 12
$115 total
Dec 11 - Dec 12
Total with taxes and fees
8.8/10 Excellent! (600 reviews)
Desk clerk (Maddy, I think?) was a breath of fresh air in a cold travel day. After a week in a Manhattan hotel, the room looks gigantic. Always great to have hot coffee waiting in the lobby.
Reviewed on Nov 28, 2025

Holiday Inn Express Corydon by IHG
249 Federal Drive Nw Corydon IN
Fully refundable
$87 nightly
The price is $97 total per night from Dec 26 to Dec 27
$97 total
Dec 26 - Dec 27
Total with taxes and fees
8.4/10 Very Good! (358 reviews)
Very clean and great staff!
Reviewed on Nov 15, 2025
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.



















