Madison Vacations from $320

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Your Madison Vacation

Take the guesswork out of travel planning with a Madison vacation package. A good neighborhood to stay in this exciting city is South Greensburg, which is good for dining and a lot more. Searching for some sightseeing tips for your trip to Madison? Big Mac Museum and Youngwood Historical and Railroad Museum are two must-visit attractions here. Expedia can help you escape the everyday. Tailor your vacation to Madison to suit your travel style, whatever that may be.

The Latest Madison vacation packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Pittsburgh University Place

Hilton Garden Inn Pittsburgh University Place

3 out of 5
Central Oakland
Price was $384, price is now $320 per person
$320
per person
Feb 11 - Feb 13
found 20 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Pittsburgh (PIT)
8.8/10 Excellent! (1,004 reviews)
The staff was awesome!

Reviewed on Jan 6, 2026

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was $571, price is now $446 per person
$446
per person
Feb 12 - Feb 15
found 7 hours ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)
7.6/10 Good! (37 reviews)
Nice rooms, beautiful building, good value, great location.

Reviewed on Jan 4, 2026

Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

3.5 out of 5
Downtown Pittsburgh
Price was $655, price is now $528 per person
$528
per person
Mar 26 - Mar 29
found 12 hours ago
Roundtrip flight included
Dallas (DAL) to Pittsburgh (PIT)
8/10 Very Good! (1,009 reviews)
Staff was great made it easy to check in. Only there for the night next to elevator kind of loud but room was cozy and comfortable!

Reviewed on Jan 7, 2026

Quality Inn Pittsburgh Airport

Quality Inn Pittsburgh Airport

2.5 out of 5
Price was $495, price is now $405 per person
$405
per person
Feb 11 - Feb 17
found 16 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Pittsburgh (PIT)
7.4/10 Good! (906 reviews)
Great room and friendly staff.

Reviewed on Jan 6, 2026

Comfort Inn & Suites Pittsburgh-Northshore

Comfort Inn & Suites Pittsburgh-Northshore

2.5 out of 5
North Side
Price was $456, price is now $376 per person
$376
per person
Feb 12 - Feb 15
found 7 hours ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)
7.6/10 Good! (323 reviews)
clean, convenient, friendly staff

Reviewed on Jan 7, 2026

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Madison Hotel Deals

Hyatt House Pittsburgh/Bloomfield/Shadyside

Hyatt House Pittsburgh/Bloomfield/Shadyside

3 out of 5
5335 Baum Blvd Pittsburgh PA
Fully refundableReserve now, pay when you stay
$142 nightly
The price is $162 total per night from Jan 22 to Jan 23
$162 total
Jan 22 - Jan 23
Total with taxes and fees
8.8/10 Excellent! (1,005 reviews)
Room was great, staff was friendly. Only one working elevator, and a slow one at that, was really tough. Hopefully they get the elevators fixed up though.

Reviewed on Dec 30, 2025

Hyatt House Pittsburgh/Bloomfield/Shadyside
Hotel Indigo Pittsburgh East Liberty by IHG

Hotel Indigo Pittsburgh East Liberty by IHG

3.5 out of 5
123 North Highland Avenue Pittsburgh PA
Fully refundable
$104 nightly
The price is $119 total per night from Jan 14 to Jan 15
$119 total
Jan 14 - Jan 15
Total with taxes and fees
7.8/10 Good! (1,013 reviews)
Yes

Reviewed on Jan 5, 2026

Hotel Indigo Pittsburgh East Liberty by IHG
Hilton Garden Inn Pittsburgh University Place

Hilton Garden Inn Pittsburgh University Place

3 out of 5
3454 Forbes Ave Pittsburgh PA
Fully refundableReserve now, pay when you stay
$117 nightly
The price is $133 total per night from Jan 26 to Jan 27
$133 total
Jan 26 - Jan 27
Total with taxes and fees
8.8/10 Excellent! (1,004 reviews)
Everything was great as always.

Reviewed on Jan 5, 2026

Hilton Garden Inn Pittsburgh University Place
See all 544 properties in Madison
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find the Best Madison Vacation Packages

Madison Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Arnold Palmer Regional Airport (LBE)
Top Sights
The Palace Theatre, Greendance Winery and West Overton Village Museum

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Frequently asked questions

How much does a Madison vacation package cost?
You'll find cheap prices from $320 on Expedia for your Madison getaway. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Madison costs.
What are the cheapest months to go to Madison?
If you're hoping to snag a cheap Madison vacation package, consider traveling in November, December and January. You'll typically find better prices on accommodations and flights during these quieter months — perfect for budget-conscious travelers.
How many days is enough for Madison?
With a well-organized itinerary, you can easily visit the most popular Madison sights in a few days. But if you'd like to explore off the beaten track or go on day trips, consider booking your Madison vacation for longer.
How to find the best Madison package deals?
Use Expedia's filter tool to find some tempting Madison package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for Madison package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Madison vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll generally land a better deal than booking each component separately. And you'll still enjoy the freedom to create a personalized Madison vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Madison?
Secure fantastic discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Madison escape.
Does Expedia offer Book Now, Pay Later Madison vacation packages?
If you're like us, you love exploring new places but are not a fan of the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the cost of your Madison trip over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.