A rusted metal bridge with blue railings, surrounded by dense green foliage.

Madison Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

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

    Plan, book, and manage your trip all in one place

Your Madison Vacation

When a break in the city is calling, answer it with a vacation package to Madison. The neighborhood of Downtown St. Louis, which is good for festivals, bars and pubs and dining, makes a fantastic base for your adventures. If your trip to Madison includes some sightseeing, visit well-known attractions like Busch Stadium, Gateway Arch and Dome at America’s Center. A few clicks is all it takes to build your ideal Madison vacation on Expedia.

Top Madison vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Dec 18 - Dec 20

    Holiday Inn St. Louis Arpt West-Earth City by IHG + Flight

    Earth City
    2 nights
    3.5 star property
    7.6/10 - Good (1,000 reviews)
    "It was clean and have no complaints."
    Reviewed November 3, 2026
    Roundtrip • Calgary (YYC) - St. Louis (STL)
    YYC - STL • 1 stop STL - YYC • 1 stop
    CA $970
    CA $911
    per traveller
    found 11 hours ago
    Holiday Inn St. Louis Arpt West-Earth City by IHG
  • Dec 18 - Dec 20

    The Wildwood Hotel + Flight

    Wildwood
    2 nights
    3.5 star property
    9.2/10 - Wonderful (1,682 reviews)
    "Everything was good. Seemed that the property was not full but we were forced into a suite."
    Reviewed November 7, 2026
    Roundtrip • Calgary (YYC) - St. Louis (STL)
    YYC - STL • 1 stop STL - YYC • 1 stop
    CA $1,284
    CA $1,000
    per traveller
    found 11 hours ago
    The Wildwood Hotel
  • Dec 18 - Dec 20

    Hampton Inn St. Charles St. Peters + Flight

    St. Charles
    2 nights
    2.5 star property
    8.2/10 - Very good (1,001 reviews)
    Roundtrip • Calgary (YYC) - St. Louis (STL)
    YYC - STL • 1 stop STL - YYC • 1 stop
    CA $992
    CA $954
    per traveller
    found 11 hours ago
    Hampton Inn St. Charles St. Peters
  • Dec 18 - Dec 20

    Hyatt Place St. Louis/Chesterfield + Flight

    Chesterfield
    2 nights
    3.0 star property
    9.6/10 - Exceptional (1,011 reviews)
    Roundtrip • Calgary (YYC) - St. Louis (STL)
    YYC - STL • 1 stop STL - YYC • 1 stop
    CA $1,034
    CA $997
    per traveller
    found 11 hours ago
    Hyatt Place St. Louis/Chesterfield
  • Dec 18 - Dec 20

    Courtyard St. Louis Airport/Earth City + Flight

    Bridgeton
    2 nights
    3.0 star property
    8.4/10 - Very good (1,001 reviews)
    Roundtrip • Calgary (YYC) - St. Louis (STL)
    YYC - STL • 1 stop STL - YYC • 1 stop
    CA $1,033
    CA $998
    per traveller
    found 11 hours ago
    Courtyard St. Louis Airport/Earth City

Madison Hotel Deals

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?

Offering great value package deals from CA $911 on Expedia, you'll be pleasantly surprised at how much a vacation to Madison costs! Our packages make travel planning easier and save you more.

What are the cheapest months to go to Madison?

January, February and November are great times to look for cheap Madison vacation packages. Choosing to travel in less busy months means you can generally find better prices on flights and hotels.

How many days is enough for Madison?

Allow at least 2 days for your Madison vacation if you want to enjoy all that makes this place special. Stroll around key areas, including Downtown St. Louis and Downtown West. Then head to the major sights like Gateway Arch and City Museum. With a good itinerary, you can keep busy with room for some rest and relaxation too. Want to travel beyond Madison? Consider squeezing in a day trip or two.

How to find the best Madison package deals?

Start your search for a Madison package deal by entering your travel dates and destination under our "Packages" tab. Then apply a few filters, like "Guest rating" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the ideal Madison package deal straight away, simply tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Madison escape off to a flying start.

Is it cheaper to book a Madison vacation as a package?

You can enjoy significant savings on your next Madison escape by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to view some great airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may land a better deal.

When to book a vacation package to Madison?

If you've got your Madison travel dates locked in, book as early as you can to grab some terrific deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are ideal for impromptu escapes.

How to plan a trip to Madison?

  1. Choose when to go: Check your diary and get packing. Your preferred season and the activities on offer will also help you decide when to visit Madison.
  2. Calculate your budget: Ensure you have enough money to cover everything from food and transportation to activities and flights. Your hotel 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 activities and attractions you'd like to get to in Madison. Then, estimate how long you'll need for each, including any travel time.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to find a Madison vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.