Madison Vacations from $187

Book a Hotel + Flight or Car together to unlock savings

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.
DoubleTree by Hilton Pittsburgh - Green Tree

DoubleTree by Hilton Pittsburgh - Green Tree

4 out of 5
Price was $247, price is now $187 per person
$187
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip flight included
New York (LGA) to Pittsburgh (PIT)
16.4/10 Exceptional! (1,000 reviews)
Staff at bar was rude, staff at check in did a poor job of telling us where to go to get to our room

Reviewed on Nov 15, 2025

Hotel Indigo Pittsburgh East Liberty by IHG

Hotel Indigo Pittsburgh East Liberty by IHG

3.5 out of 5
East Liberty
Price was $288, price is now $198 per person
$198
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip flight included
New York (LGA) to Pittsburgh (PIT)
16/10 Exceptional! (1,004 reviews)
Their breakfast deal was a wonderful meal at their in house restaurant.

Reviewed on Nov 7, 2025

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was $439, price is now $326 per person
$326
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip flight included
New York (LGA) to Pittsburgh (PIT)
17.2/10 Exceptional! (1,001 reviews)
Just average. Rooms dated

Reviewed on Nov 3, 2025

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
Price was $345, price is now $257 per person
$257
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip flight included
New York (LGA) to Pittsburgh (PIT)
16.8/10 Exceptional! (1,383 reviews)
Loved the lobby and unique decor. Server at Millhouse was exceptional.

Reviewed on Nov 11, 2025

Residence Inn by Marriott Pittsburgh North Shore

Residence Inn by Marriott Pittsburgh North Shore

3 out of 5
North Shore
Price was $392, price is now $293 per person
$293
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip flight included
New York (LGA) to Pittsburgh (PIT)
16.8/10 Exceptional! (1,005 reviews)
The check inn staff was rude and kept walking away and talking to other people while i was being checked in. Didnt tell me about breakfast or how parking worked.

Reviewed on Nov 15, 2025

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Madison Hotel Deals

Comfort Inn & Suites Pittsburgh Fox Chapel

Comfort Inn & Suites Pittsburgh Fox Chapel

2.5 out of 5
180 Gamma Drive Pittsburgh PA
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $91 total per night from Nov 23 to Nov 24
$91 total
Nov 23 - Nov 24
Total with taxes and fees
6/10 (1,007 reviews)
Room clean & quiet

Reviewed on Nov 11, 2025

Comfort Inn & Suites Pittsburgh Fox Chapel
Hampton Inn Pittsburgh/Monroeville

Hampton Inn Pittsburgh/Monroeville

2.5 out of 5
3000 Mosside Blvd Monroeville PA
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $109 total per night from Dec 14 to Dec 15
$109 total
Dec 14 - Dec 15
Total with taxes and fees
8/10 Very Good! (1,143 reviews)
The room was very clean, comfortable with a good appearance. The staff was very thoughtful, kind and friendly. Breakfast there is very satisfying as well.

Reviewed on Nov 11, 2025

Hampton Inn Pittsburgh/Monroeville
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
$115 nightly
The price is $131 total per night from Nov 27 to Nov 28
$131 total
Nov 27 - Nov 28
Total with taxes and fees
8.8/10 Excellent! (1,001 reviews)
Friendly staff, clean space, and great price

Reviewed on Nov 7, 2025

Hilton Garden Inn Pittsburgh University Place
See all 531 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 $187 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.