Madison Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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

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    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.
  • An outdoor patio with a fire pit, seating area, and a TV screen.
    Jan 6 - Jan 12

    Courtyard by Marriott Pittsburgh Washington/Meadow Lands + Flight

    Washington
    6 nights
    3.0 star property
    8.6/10 - Excellent (1,002 reviews)
    "Stayed the night before a Pittsburgh Steelers football game. It was very clean and the staff is friendly and helpful. We went to the outlet and shopped for a little while."
    Reviewed November 15, 2026
    Roundtrip • Vancouver (YVR) - Pittsburgh (PIT)
    YVR - PIT • 1 stop PIT - YVR • 1 stop
    CA $1,142
    CA $934
    per traveller
    found 1 day ago
    Courtyard by Marriott Pittsburgh Washington/Meadow Lands
  • A modern hotel room with a large window, a sofa, and a dining area.
    Jan 25 - Jan 30

    Fairmont Pittsburgh + Flight

    Downtown Pittsburgh
    5 nights
    4.5 star property
    8.8/10 - Excellent (1,002 reviews)
    Roundtrip • Halifax (YHZ) - Pittsburgh (PIT)
    YHZ - PIT • 1 stop PIT - YHZ • 1 stop
    CA $1,812
    CA $1,446
    per traveller
    found 11 hours ago
    Fairmont Pittsburgh
  • A modern bar area with a marble countertop, bar stools, and a bookshelf filled with books and decorative items.
    Jan 25 - Jan 30

    The Oaklander Hotel, Autograph Collection + Flight

    Oakland
    5 nights
    4.5 star property
    9.2/10 - Wonderful (860 reviews)
    "The room was enormous with huge window, so lots of light. The bathroom was spacious and modern. Good quality bath products in large containers so no wasteful mini bottles There was lots of closet and storage space. There was a coffee bar in the room and plenty of bottled water. Room also had a generous sized desk."
    Reviewed November 13, 2026
    Roundtrip • Halifax (YHZ) - Pittsburgh (PIT)
    YHZ - PIT • 1 stop PIT - YHZ • 1 stop
    CA $1,679
    CA $1,353
    per traveller
    found 11 hours ago
    The Oaklander Hotel, Autograph Collection
  • A cityscape with high-rise buildings, including a prominent Westin hotel.
    Jan 25 - Jan 30

    The Westin Pittsburgh, a Marriott Hotel + Flight

    Downtown Pittsburgh
    5 nights
    4.0 star property
    8.6/10 - Excellent (1,002 reviews)
    "great"
    Reviewed November 14, 2026
    Roundtrip • Halifax (YHZ) - Pittsburgh (PIT)
    YHZ - PIT • 1 stop PIT - YHZ • 1 stop
    CA $1,533
    CA $1,265
    per traveller
    found 11 hours ago
    The Westin Pittsburgh, a Marriott Hotel
  • A modern hotel lobby with a central seating area, large windows, and contemporary furnishings.
    Jan 25 - Jan 30

    Hyatt Regency Pittsburgh International Airport + Flight

    Pittsburgh
    5 nights
    3.5 star property
    9.0/10 - Wonderful (1,807 reviews)
    "We stayed one night since we had an early flight. The hotel is clean and has all the amenities but was the loudest hotel we have stayed in. There was noise from the rooms around and above us and from the hallway. We also were woken up at 4am by some loud vibrations within the wall. No one could have slept through the noise. When we brought it to their attention, they apologized but that didn’t help with our sleepless night before a long day of travel. We would stay again only if absolutely..."
    Reviewed November 14, 2026
    Roundtrip • Halifax (YHZ) - Pittsburgh (PIT)
    YHZ - PIT • 1 stop PIT - YHZ • 1 stop
    CA $1,397
    CA $1,164
    per traveller
    found 10 hours ago
    Hyatt Regency Pittsburgh International Airport

Discover the most popular places to visit in Madison

Madison Park

After visiting Madison Park, make a plan to see the other sights and activities in Madison.
See properties

Madison Hotel Deals

A swimming pool with lounge chairs and a lifeguard sign.

Hampton Inn & Suites Pittsburgh New Stanton

Hampton Inn & Suites Pittsburgh New Stanton
2.5 star property
6.2 km from Madison
9.6 out of 10, Exceptional, (796 reviews)
The price is CA $132
CA $147 total
includes taxes & fees
Dec 6 - Dec 7
Hampton Inn & Suites Pittsburgh New Stanton
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.
See all properties in Madison

Frequently Asked Questions

How much does a Madison vacation package cost?

You'll find cheap prices from CA $934 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.