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.
Wyndham Grand Pittsburgh Downtown
Downtown Pittsburgh
CA $1,140
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Pittsburgh (PIT)
8.2/10 Very good! (3,705 reviews)
The hotel is in a very easy to access location. Valet parking was convenient. The staff from check in to an evening drink at the bar to breakfast were all exceptionally nice and helpful. Our room had a gorgeous river view and very comfortable beds. The bathroom was good. It could have used some upgrades to the shower doors that were difficult to close and the sliding door between the bathroom and the sleeping area was annoying to use also.
Reviewed on Aug 22, 2026
The Atterbury Hotel, Autograph Collection
Downtown Pittsburgh
CA $1,398
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Pittsburgh (PIT)
9/10 Wonderful! (1,010 reviews)
Room service not available. No help in obtaining local tour indoor booking.
Mike, in the lobby, was an amazing help!!
Reviewed on Aug 21, 2026
Crowne Plaza Suites Pittsburgh South by IHG
CA $1,294
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Pittsburgh (PIT)
8.6/10 Excellent! (1,017 reviews)
Real nice hotel - a lot of value for money ; pool is nonexistent, but other amenities are just as advertised. Clean rooms. Friendly service. Good food. What more could you want?
Reviewed on Aug 21, 2026
EVEN Hotel Pittsburgh Downtown by IHG
Downtown Pittsburgh
CA $1,297
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Pittsburgh (PIT)
8.8/10 Excellent! (1,090 reviews)
I have no complaints on the hotel it was great I felt safe and everyone was super friendly
Reviewed on Aug 21, 2026
Ready to book your vacation to Madison?
Madison Hotel Deals
Hyatt House Pittsburgh/Bloomfield/Shadyside
5335 Baum Blvd Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $172
CA $196 total
Aug 30 - Aug 31
includes taxes & fees
9/10 Wonderful! (1,022 reviews)
"Very satisfied!"
Reviewed on Aug 21, 2026
Hilton Garden Inn Pittsburgh University Place
3454 Forbes Ave Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $164
CA $187 total
Sep 7 - Sep 8
includes taxes & fees
Hotel Indigo Pittsburgh East Liberty by IHG
123 North Highland Avenue Pittsburgh PA
Fully refundable
CA $129
CA $147 total
Aug 30 - Aug 31
includes taxes & fees
8.2/10 Very good! (1,027 reviews)
"The staff was very kind and courteous. The wall decor was unique and fun. The breakfast food unfortunately had no flavor and was missing key ingredients like cheese, and ketchup. They didn’t have any apparently. There were no desserts to order from the dessert menu the night before either. They don’t ..."
Reviewed on Aug 20, 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 $1,140 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.
