Madison Vacations from $398

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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.
Quality Inn Waynesburg - Morrisville

Quality Inn Waynesburg - Morrisville

2.5 out of 5
Price was $556, price is now $398 per person
$398
per person
Nov 2 - Nov 5
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
6.6/10 (361 reviews)
This place is very dated. The staff wants to hang out and party. I would not take my family there

Reviewed on Jul 18, 2025

Ohiopyle Suites

Ohiopyle Suites

2 out of 5
Price was $708, price is now $488 per person
$488
per person
Nov 2 - Nov 5
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
8.8/10 Excellent! (235 reviews)
The location was perfect for my group of 4 former coworkers from different areas of the country to get reacquainted, through some whitewater rafting, biking and drinking.

Reviewed on Sep 17, 2025

Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $685, price is now $475 per person
$475
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
7.8/10 Good! (179 reviews)
The stay was wonderful - the property is located within walking distance of the convention center and has a Target nearby as well as great restaurants. The area nearby can be a little noisy at night with loud cards driving by, but overall the property was well kept and the host's communication was quick and thorough. I'd be happy to stay here again.

Reviewed on Sep 27, 2025

Hilton Garden Inn Uniontown

Hilton Garden Inn Uniontown

3 out of 5
Price was $693, price is now $502 per person
$502
per person
Nov 2 - Nov 5
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
9/10 Wonderful! (589 reviews)
We enjoyed the pool and hot tub. Nice hotel. Big room. Shower was different but worked perfectly. Firepit was an attraction at night, lobby was lively with what seemed to be a big family hanging out. My obversations were made while I enjoyed the bar and college football with a bunch of Priests. Labor Day weekend is an annual Catholic pilgrimage in uniontown. True story.

Reviewed on Sep 11, 2025

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $627, price is now $455 per person
$455
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Pittsburgh (PIT)
7.6/10 Good! (22 reviews)
Thank you Josh for helping us with our second reservation. The hotel is elegant with old school charm. The suites has washer/ dryers and full kitchen and very friendly to us bicyclists

Reviewed on Sep 22, 2025

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Madison Hotel Deals

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
$152 nightly
The price is $173 total per night from Oct 29 to Oct 30
$173 total
Oct 29 - Oct 30
Total with taxes and fees
8.8/10 Excellent! (1,003 reviews)
"Great"

Reviewed on Sep 25, 2025

Hilton Garden Inn Pittsburgh University Place
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
$105 nightly
The price is $120 total per night from Oct 20 to Oct 21
$120 total
Oct 20 - Oct 21
Total with taxes and fees
8/10 Very Good! (1,105 reviews)
"."

Reviewed on Sep 22, 2025

Hampton Inn Pittsburgh/Monroeville
The Maverick by Kasa

The Maverick by Kasa

3 out of 5
120 S Whitfield St, Pittsburgh, PA
$88 nightly
The price is $101 total per night from Oct 5 to Oct 6
$101 total
Oct 5 - Oct 6
Total with taxes and fees
8.8/10 Excellent! (753 reviews)
"It was a fantastic time would stay again"

Reviewed on Sep 24, 2025

The Maverick by Kasa
See all 518 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.

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Frequently asked questions

How much does a Madison vacation package cost?
You'll find cheap prices from $398 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.