Search Deals onCarefree Vacation Packages
Carefree Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Santas Lodge and Resort
Price was $558, price is now $430 per person
$430
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Louisville (SDF)
Stay at this hotel in Santa Claus. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Holiday World and Splashin' Safari and Frosty's Fun Center are located nearby.
Regina's Country Livin'
Price was $770, price is now $663 per person
$663
per person
Jan 27 - Jan 31
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Louisville (SDF)
Stay at this B&B in Finchville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Talon Winery and Jeptha Creed Distillery are located nearby.
If I am ever doing something between Louisville and Lexington, I will be visiting Regina. This house was well-designed as a true BNB with excellent access/security, thoughtful decor, and an extremely welcoming atmosphere. The reviews praising the breakfast are true - but don't just go for the biscuits and gravy, go for the full experience.
Reviewed on Sep 28, 2026
Omni Louisville Hotel
Price was $799, price is now $689 per person
$689
per person
Feb 2 - Feb 4
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
Book a stay at this spa hotel in Louisville. Enjoy a full-service spa, 3 restaurants, and 3 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fourth Street Live! and KFC Yum Center are located nearby.
Hotel Distil, Autograph Collection
Price was $770, price is now $674 per person
$674
per person
Feb 2 - Feb 4
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
Book a stay at this business-friendly hotel in Louisville. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Whiskey Row and KFC Yum Center are located nearby.
Marriott Louisville East
Price was $836, price is now $737 per person
$737
per person
Jan 19 - Jan 24
found 18 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
Book a stay at this business-friendly hotel in Louisville. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hunnington Place Shopping Center and Jeffersontown Commons Shopping Center are located nearby.
Hyatt Regency Louisville
Price was $696, price is now $619 per person
$619
per person
Dec 22 - Dec 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
Book a stay at this business-friendly hotel in Louisville. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fourth Street Live! and KFC Yum Center are located nearby.
Bed was hard but good stay
Reviewed on Nov 14, 2026
Studio 6 Suites Louisville, KY – Airport/Expo Center
Price was $609, price is now $544 per person
$544
per person
Jan 19 - Jan 24
found 18 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
Stay at this hotel in Louisville. Enjoy free parking, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Kentucky Kingdom and L&N Federal Credit Union Stadium are located nearby.
Ok
Reviewed on Nov 13, 2026
SpringHill Suites by Marriott Louisville Downtown
Price was $630, price is now $569 per person
$569
per person
Feb 2 - Feb 4
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
Book a stay at this business-friendly hotel in Louisville. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Whiskey Row and KFC Yum Center are located nearby.
Carefree Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Carefree Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Fri, Dec 18 - Mon, Dec 21
PIE
St. Petersburg-Clearwater Intl.
SDF
Louisville Intl.
$128 Roundtrip, found 3 days ago
$128
Roundtrip
found 3 days ago
Thu, Dec 17 - Sun, Dec 20
TPA
Tampa Intl.
SDF
Louisville Intl.
$137 Roundtrip, found 5 hours ago
$137
Roundtrip
found 5 hours ago
Mon, Dec 7 - Wed, Dec 9
MSP
Minneapolis - St. Paul Intl.
SDF
Louisville Intl.
$254 Roundtrip, found 2 hours ago
$254
Roundtrip
found 2 hours ago
Mon, Jan 25 - Sat, Jan 30
BOS
Logan Intl.
SDF
Louisville Intl.
$269 Roundtrip, found 23 hours ago
$269
Roundtrip
found 23 hours ago
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