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

Hancock House

3 out of 5
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

Crowne Plaza Louisville Airport Expo Ctr by IHG

3.5 out of 5
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

Holiday Inn Louisville Airport South by IHG

3 out of 5
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

Galt House Hotel Trademark Collection by Wyndham

4 out of 5
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

Santas Lodge and Resort

2.5 out of 5
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

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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
$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

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
$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

Hampton Inn 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 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

Holiday Inn Express Corydon by IHG
See all 158 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 $253 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.