Search Deals onWestern Kentucky Vacation Packages
Western Kentucky Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Regina's Country Livin'
Price was $739, price is now $607 per person
$607
per person
Nov 11 - Nov 15
found 21 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) 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.
For my first time visiting in Kentucky, I’m glad I picked to stay at Regina’s Country Living. Hostess : Top notch hospitality; Regina looked out for everyone who stayed for the Kentucky Derby event like a mother. Our breakfast was homemade each morning, and it definitely brought back memories with of my grandma for Sunday and Christmas breakfast specials.
Room/Home : Regina’s home had so much old southern world charm that had it not been so cool outside, that drinking a Mint Julep on the porch would have been a pleasant experience. I stayed in the “ King’s Room “, my bed was huge and the covers were soft and inviting. I slept good everyday I was there and I slept really good after the Derby. Each room had a story to tell and I’d especially liked the sky light in the family room. The park adjacent to the house is such a nice addition for anyone who just wants to take a walk or run. It’s perfect if you bring a dog with you on your stay as well.
Thank you, Regina for opening up your home and being an amazing woman. Thank you for sharing an amazing friendly dinner with me at the Mexican restaurant and making sure a solo traveler felt like family even if it was for a few days. Looking forward to next year’s Kentucky Derby at your Bed and Breakfast.
Reviewed on May 4, 2026

Pillow and Paddock B&B
Save 100% on your flight
Price was $1,315, price is now $940 per person
$940
per person
Nov 11 - Nov 15
found 21 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) 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 Purple Martin
Price was $1,188, price is now $881 per person
$881
per person
Nov 11 - Nov 15
found 21 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) 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 $1,262, price is now $999 per person
$999
per person
Nov 11 - Nov 15
found 21 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) 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 KFC Yum Center and Louisville Slugger Museum are located nearby.
We had a wonderful time with a group of 8 of us. Valet was perfect! Access to the the bar was fabulous and good. We ordered drinks and desserts and enjoyed the ambiance. Would highly recommend.
Reviewed on Sep 7, 2026

Cottonwood Airport & Expo Hotel Louisville
Price was $872, price is now $699 per person
$699
per person
Dec 3 - Dec 6
found 24 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.
A lot of running around the hallways at 1am. there must of been some kind of family reunion/wedding or something. The day checking out one of the two elevators was inoperable. that was truly a bummer having to try to use the stairs or wait 20 minutes for the elevator.
Reviewed on Sep 8, 2026

The Bellwether Hotel
Price was $915, price is now $744 per person
$744
per person
Nov 11 - Nov 15
found 21 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) to Louisville (SDF)
Stay at this aparthotel in Louisville. Enjoy free WiFi, premium bedding, and bathrobes. Popular attractions KFC Yum Center and Louisville Slugger Museum are located nearby.
This is a hotel not to be missed. The Art Deco style in the rooms combined with the cleanliness and boutique style makes it a Louisville treasure. Plenty of street parking and a great neighborhood.
Reviewed on Sep 8, 2026

Omni Louisville Hotel
Price was $1,579, price is now $1,291 per person
$1,291
per person
Oct 14 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Seattle (SEA) 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 KFC Yum Center and Whiskey Row are located nearby.

The Grady
Price was $850, price is now $697 per person
$697
per person
Dec 3 - Dec 6
found 23 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.
Western Kentucky Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Western Kentucky 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.

Sat, Sep 19 - Tue, Oct 6
ORD
O'Hare Intl.
EVV
Evansville Regional
$486 Roundtrip, found 11 hours ago
$486
Roundtrip
found 11 hours ago

Sat, Sep 19 - Tue, Oct 6
ORD
O'Hare Intl.
EVV
Evansville Regional
$531 Roundtrip, found 11 hours ago
$531
Roundtrip
found 11 hours ago

Wed, Sep 9 - Sun, Sep 13
CLT
Charlotte-Douglas Intl.
EVV
Evansville Regional
$554 Roundtrip, found 21 hours ago
$554
Roundtrip
found 21 hours ago

Sat, Sep 19 - Tue, Oct 6
ORD
O'Hare Intl.
EVV
Evansville Regional
$696 Roundtrip, found 11 hours ago
$696
Roundtrip
found 11 hours ago
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