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Southern Indiana Vacation Packages

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Southern Indiana Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Brown Hotel

The Brown Hotel

4.5 out of 5
Price was $640, price is now $506 per person
$506
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Louisville (SDF)
Book a stay at this luxury 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 KFC Yum Center and Whiskey Row are located nearby.

Pillow and Paddock B&B

Pillow and Paddock B&B

3.5 out of 5
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 1 day 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

The Grady

4 out of 5
Price was $1,300, price is now $940 per person
$940
per person
Dec 26 - Jan 2
found 1 day 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

The Purple Martin

2 out of 5
Price was $1,799, price is now $1,405 per person
$1,405
per person
Dec 27 - Jan 3
found 1 day 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

Hotel Distil, Autograph Collection

4 out of 5
Price was $1,868, price is now $1,469 per person
$1,469
per person
Dec 27 - Jan 3
found 1 day 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.

Cottonwood Airport & Expo Hotel Louisville

Cottonwood Airport & Expo Hotel Louisville

3.5 out of 5
Price was $1,162, price is now $923 per person
$923
per person
Dec 27 - Jan 3
found 1 day 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.
Plumbing issues Shower drain and toilet

Reviewed on Oct 23, 2026

Hotel Bourré Bonne Louisville, Curio Collection by Hilton

Hotel Bourré Bonne Louisville, Curio Collection by Hilton

4 out of 5
Price was $1,230, price is now $981 per person
$981
per person
Dec 26 - Jan 2
found 1 day 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.

Southern Indiana Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Cottonwood Airport & Expo Hotel Louisville

Cottonwood Airport & Expo Hotel Louisville

3.5 out of 5
Shively
Price was $570, price is now $451 per person
$451
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Louisville (SDF)
Hyatt Regency Louisville

Hyatt Regency Louisville

4 out of 5
Downtown Louisville
Price was $634, price is now $482 per person
$482
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Louisville (SDF)
The Grady

The Grady

4 out of 5
Downtown Louisville
Price was $748, price is now $573 per person
$573
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Louisville (SDF)
The Brown Hotel

The Brown Hotel

4.5 out of 5
Downtown Louisville
Price was $640, price is now $506 per person
$506
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Louisville (SDF)

Southern Indiana Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Brown Hotel

The Brown Hotel

4.5 out of 5
Downtown Louisville
Price was $709, price is now $524 per person
$524
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Louisville (SDF)
Pillow and Paddock B&B

Pillow and Paddock B&B

3.5 out of 5
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 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
The Grady

The Grady

4 out of 5
Downtown Louisville
Price was $1,300, price is now $940 per person
$940
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
The Purple Martin

The Purple Martin

2 out of 5
Price was $1,799, price is now $1,405 per person
$1,405
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Mon, Nov 23 - Tue, Dec 1
ATL
Hartsfield-Jackson Atlanta Intl.
CVG
Cincinnati - Northern Kentucky Intl.
$44 Roundtrip, found 1 day ago
$44
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Nov 23 from Hartsfield-Jackson Atlanta Intl. to Cincinnati - Northern Kentucky Intl., returning Tue, Dec 1, priced at $44 found 1 day ago
Frontier Airlines
Wed, Dec 2 - Wed, Dec 16
DFW
Dallas-Fort Worth Intl.
CVG
Cincinnati - Northern Kentucky Intl.
$114 Roundtrip, found 1 hour ago
$114
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Wed, Dec 2 from Dallas-Fort Worth Intl. to Cincinnati - Northern Kentucky Intl., returning Wed, Dec 16, priced at $114 found 1 hour ago
Frontier Airlines
Fri, Dec 11 - Wed, Dec 23
DEN
Denver Intl.
CVG
Cincinnati - Northern Kentucky Intl.
$199 Roundtrip, found 14 hours ago
$199
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Fri, Dec 11 from Denver Intl. to Cincinnati - Northern Kentucky Intl., returning Wed, Dec 23, priced at $199 found 14 hours ago
Allegiant Air
Thu, Nov 19 - Sun, Nov 22
EWR
Newark Liberty Intl. Airport
CVG
Cincinnati - Northern Kentucky Intl.
$200 Roundtrip, found 6 hours ago
$200
Roundtrip
found 6 hours ago
Select Allegiant Air flight, departing Thu, Nov 19 from Newark Liberty Intl. Airport to Cincinnati - Northern Kentucky Intl., returning Sun, Nov 22, priced at $200 found 6 hours ago

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