Search Deals onCarefree Vacation Packages
Carefree Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Cottonwood Airport & Expo Hotel Louisville
Price was $1,162, price is now $923 per person
$923
per person
Dec 27 - Jan 3
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
Book a stay at this business-friendly hotel in Louisville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Churchill Downs and L&N Federal Credit Union Stadium are located nearby.
Pillow and Paddock B&B
Save 100% on your flight
Price was $2,680, price is now $1,750 per person
$1,750
per person
Dec 27 - Jan 3
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
Stay at this B&B in La Grange. Enjoy free WiFi, breakfast (surcharge), and onsite spa services. Popular attractions Lagrange Quarry and Walsh Park are located nearby.
Courteous staff and the room was outstanding. It was our second stay at the inn. Everything is first class. We highly recommend it.
Reviewed on Dec 22, 2025
The Grady
Price was $1,300, price is now $940 per person
$940
per person
Dec 26 - Jan 2
found 14 hours ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
Stay at this hotel in Louisville. Enjoy free WiFi, breakfast (surcharge), and valet parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Louisville Slugger Museum and KFC Yum Center are located nearby.
The Purple Martin
Price was $1,799, price is now $1,405 per person
$1,405
per person
Dec 27 - Jan 3
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
Book a stay at this golf hotel in Prospect. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Chamberlain Pointe Shopping Center and Old Brownsboro Crossing Shopping Center are located nearby.
Amazing property… I would come back in a heartbeat!
Reviewed on Jun 19, 2025
Hotel Distil, Autograph Collection
Price was $1,868, price is now $1,469 per person
$1,469
per person
Dec 27 - Jan 3
found 10 hours ago
Roundtrip 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.
Hotel Bourré Bonne Louisville, Curio Collection by Hilton
Price was $1,230, price is now $981 per person
$981
per person
Dec 26 - Jan 2
found 14 hours ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
Book a stay at this business-friendly hotel in Louisville. Enjoy an outdoor pool, 2 restaurants, and 3 bars/lounges. Popular attractions KFC Yum Center and Whiskey Row are located nearby.
Louisville Marriott Downtown
Price was $1,331, price is now $1,065 per person
$1,065
per person
Dec 26 - Jan 2
found 14 hours ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
Book a stay at this business-friendly hotel in Louisville. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions KFC Yum Center and Whiskey Row 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.
Thu, Nov 5 - Thu, Nov 19
TPA
Tampa Intl.
SDF
Louisville Intl.
$180 Roundtrip, found 8 hours ago
$180
Roundtrip
found 8 hours ago
Mon, Nov 23 - Tue, Dec 8
DFW
Dallas-Fort Worth Intl.
SDF
Louisville Intl.
$221 Roundtrip, found 14 hours ago
$221
Roundtrip
found 14 hours ago
Thu, Nov 26 - Sat, Dec 5
DAL
Love Field
SDF
Louisville Intl.
$221 Roundtrip, found 14 hours ago
$221
Roundtrip
found 14 hours ago
Thu, Nov 12 - Tue, Nov 17
LAX
Los Angeles Intl.
SDF
Louisville Intl.
$262 Roundtrip, found 7 hours ago
$262
Roundtrip
found 7 hours ago
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