Madison Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Top Madison Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Inn on Negley
Shadyside
CA $1,285
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pittsburgh (PIT)
10/10 Exceptional! (225 reviews)
This Inn is beautiful, perfectly located within a couple minutes of downtown, very well maintained, breakfast was wonderful, the room was super comfortable with quality linens and a very comfortable batch. Wonderful staff as well, Peter gave us some history of Pittsburgh and some ideas to make our trip back home even better! We plan on coming back to Pittsburgh and staying here again.
Reviewed on Sep 30, 2026
Ready to book your vacation to Madison?
Madison Hotel Deals
The Maverick by Kasa
120 S Whitfield St Pittsburgh PA
CA $160
CA $183 total
Oct 13 - Oct 14
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
"Loved the location being so central to the entire city. I wish I could have been able to connect my phone to the TV. There appears to be a way, but for some reason my phone couldn't connect and the TV did not have the streaming services I use so I had to watch stuff on my phone. The fridge has a ..."
Reviewed on Oct 5, 2026
Hyatt House Pittsburgh/Bloomfield/Shadyside
5335 Baum Blvd Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $186
CA $212 total
Nov 3 - Nov 4
includes taxes & fees
Comfort Inn & Suites Pittsburgh Fox Chapel
180 Gamma Drive Pittsburgh PA
Fully refundable
CA $118
CA $135 total
Nov 1 - Nov 2
includes taxes & fees
5.6/10 (1,014 reviews)
"The whole place smelled like mildew and mold. The hallway was filled with the smell of marijuana and the staff was super rood. I called the front desk to ask about the mildew and pot smells and the staff person hung up on me. Don't stay on the ground floor if you have to. Avoid if you can."
Reviewed on Oct 6, 2026
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.
Stay near popular Madison attractions
Madison Park
After visiting Madison Park, make a plan to see the other sights and activities in Madison.
Frequently asked questions
How much does a Madison vacation package cost?
You'll find cheap prices from CA $1,285 on Expedia for your Madison break. 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?
January, February and March are great times to search for cheap Madison vacation packages. Opting to travel in less busy periods means you'll typically find reduced prices on hotels and flights.
How many days is enough for Madison?
With a well-planned schedule, you can easily tick off the top Madison attractions in a handful of days. But if you prefer to discover hidden spots or go on day trips, consider booking your Madison vacation for longer.
How to find the best Madison package deals?
Finding a cheap Madison package deal is easy with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget, add some filters and see what's available. You can tailor your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Madison package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
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, hotel and flight into one great-value price and you could save hundreds of dollars. You'll usually get a better deal than booking each component individually. And you'll still get the flexibility to create a personalized Madison vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Madison?
If you've got your Madison vacation dates finalized, book as soon as you can to score some incredible deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are perfect for travelling on a whim.
How to plan a trip to Madison?
- Pick the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to go to Madison.
- Calculate your budget: Make sure you have enough money to cover everything from transportation and food to activities and airfares. Your accommodations will likely be the largest expense during your trip to Madison.
- Set the duration of your trip: Start by making a list of all the attractions and activities you want to experience in Madison. Then, estimate how long you'll need at each, as well as any travel time.
- Combine your airfare and accommodations: Once you've settled on your travel dates and duration, lock in the right Madison vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
