Madison Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, 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.
Hotel Indigo Pittsburgh East Liberty by IHG
Wyndham Grand Pittsburgh Downtown
Placemakr Downtown Pittsburgh
Omni William Penn Hotel
Renaissance Pittsburgh Hotel

Ready to book your vacation to Madison?

 

Choose your dates

Madison Hotel Deals

Hampton Inn Pittsburgh University/Medical Center
Hampton Inn Pittsburgh University/Medical Center
2.5 out of 5
3315 Hamlet Street, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is CA $140 per night from Jul 27 to Jul 28
CA $140
CA $159 total
Jul 27 - Jul 28
includes taxes & fees
8/10 Very Good! (1,046 reviews)
"Great staff + room was nice. Great place to stay while attending a show at Petersen."

Reviewed on Jun. 30, 2025

Hampton Inn Pittsburgh University/Medical Center
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
The price is CA $147 per night from Jul 27 to Jul 28
CA $147
CA $167 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very Good! (1,020 reviews)
"It’s ageless"

Reviewed on Jul. 13, 2025

Hotel Indigo Pittsburgh East Liberty by IHG
The Maverick by Kasa
The Maverick by Kasa
3 out of 5
120 S Whitfield St, Pittsburgh, PA
The price is CA $110 per night from Jul 20 to Jul 21
CA $110
CA $126 total
Jul 20 - Jul 21
includes taxes & fees
8.8/10 Excellent! (671 reviews)
"It was a nice place to stay, but not for an extended period of time. A few days would have been perfect. No negative reflection on the hotel, but it would be cool if they offered a gym for workouts, also the windows were dirty, due to just the elements. The windows are so big and its fun to sit and ..."

Reviewed on Jul. 12, 2025

The Maverick by Kasa
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.

Frequently asked questions

How much does a Madison vacation package cost?
You'll find cheap prices from CA $644 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.