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Madison Vacation Packages

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Madison Flight + Hotel Packages

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
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

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 $1,496, price is now $1,147 per person
$1,147
per person
Dec 27 - Jan 3
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.

TownePlace Suites by Marriott Louisville Airport

TownePlace Suites by Marriott Louisville Airport

3 out of 5
Price was $1,175, price is now $956 per person
$956
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 helpful staff in our reviews. Popular attractions Louisville Mega Cavern and Kentucky Kingdom are located nearby.
Nice spot for an overnight stay.

Reviewed on Oct 5, 2026

Bashford Manor Inn

Bashford Manor Inn

3 out of 5
Price was $1,540, price is now $1,265 per person
$1,265
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 B&B in Louisville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Louisville Mega Cavern and Louisville Zoo are located nearby.
Like old house and antiques, and historical documents and pictures. Breakfast was all you can eat

Reviewed on Oct 19, 2026

Madison Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
voco The Clair Cincinnati Downtown by IHG

voco The Clair Cincinnati Downtown by IHG

4 out of 5
Downtown Cincinnati
Price was $612, price is now $542 per person
$542
per person
Dec 4 - Dec 7
found 14 hours ago
Roundtrip flight included
Phoenix (PHX) to Cincinnati (CVG)
Pillow and Paddock B&B

Pillow and Paddock B&B

3.5 out of 5
Price was $1,932, price is now $1,449 per person
$1,449
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Louisville (SDF)
Hotel Covington Cincinnati Riverfront

Hotel Covington Cincinnati Riverfront

4 out of 5
Central Business District
Price was $825, price is now $717 per person
$717
per person
Dec 4 - Dec 7
found 14 hours ago
Roundtrip flight included
Phoenix (PHX) to Cincinnati (CVG)
The Lytle Park Hotel, Autograph Collection

The Lytle Park Hotel, Autograph Collection

5 out of 5
Downtown Cincinnati
Price was $1,240, price is now $1,110 per person
$1,110
per person
Dec 18 - Dec 21
found 14 hours ago
Roundtrip flight included
Phoenix (PHX) to Cincinnati (CVG)

Madison Vacation Packages 5-7 Night Stays

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

The Grady

4 out of 5
Downtown Louisville
Price was $1,496, price is now $1,147 per person
$1,147
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 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)
Hotel Distil, Autograph Collection

Hotel Distil, Autograph Collection

4 out of 5
Downtown Louisville
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)

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 2 days ago
$44
Roundtrip
found 2 days 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 2 days ago
Frontier Airlines
Wed, Dec 2 - Wed, Dec 16
DFW
Dallas-Fort Worth Intl.
CVG
Cincinnati - Northern Kentucky Intl.
$114 Roundtrip, just found
$114
Roundtrip
just found
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 just found
Frontier Airlines
Fri, Dec 11 - Wed, Dec 23
DEN
Denver Intl.
CVG
Cincinnati - Northern Kentucky Intl.
$165 Roundtrip, found 13 hours ago
$165
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Fri, Dec 11 from Denver Intl. to Cincinnati - Northern Kentucky Intl., returning Wed, Dec 23, priced at $165 found 13 hours ago
Allegiant Air
Thu, Nov 19 - Sun, Nov 22
EWR
Newark Liberty Intl. Airport
CVG
Cincinnati - Northern Kentucky Intl.
$178 Roundtrip, found 1 hour ago
$178
Roundtrip
found 1 hour 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 $178 found 1 hour ago