Madison Vacation Packages
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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.
The Wildwood Hotel
CA $1,030
per person
Sep 25 - Sep 28
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Louis (STL)
9.2/10 Wonderful! (1,672 reviews)
Very nice hotel in a very nice neighborhood. It felt safe and comfortable in the community since we were trying to avoid the downtown St Louis area and its traffic.. Our room was with a balcony which the front desk was very helpful in arranging for us. I would go back for sure if traveling in the area.
Reviewed on Aug 9, 2026
The Cheshire
CA $1,172
per person
Sep 25 - Sep 28
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Louis (STL)
8.8/10 Excellent! (1,006 reviews)
When checking in, the staff woman was less than friendly. There seemed to be a situation with another upset guest that may have caused the unpleasant nature. Once we entered the room, we noticed right away a musty smell. The AC did not seem to be working correctly. Though it never got hot, it also never got any cooler. The furniture had visible stains and a few of the pillow cases had staining as well. The pillows themselves are downed pillows and once you lay on them, they flatten out thin. We requested a few extra pillows that were supposed to be brought to our room which never arrived. We requested more towels which were also supposed to be brought to our room which also never arrived. Breakfast on morning one for us which was Sunday was great, however it was apparent that the fruit and pastries were being reused daily and by our check out morning on Tuesday they were no good. The pool area was decent. You have to reserve the canopy so it was unusable to us. Overall, our stay was okay. I wouldn’t say it was awful but I wouldn’t say it was great either. We don’t intend on staying in the future.
Reviewed on Aug 9, 2026
Ready to book your vacation to Madison?
Madison Hotel Deals
Hyatt Regency St. Louis at The Arch
315 Chestnut St St. Louis MO
Fully refundableReserve now, pay when you stay
CA $187
CA $220 total
Aug 28 - Aug 29
includes taxes & fees
8.6/10 Excellent! (4,220 reviews)
"Very nice and clean. Wish the rooms got a little colder"
Reviewed on Aug 10, 2026
Clayton Plaza Hotel & Extended Stay
7750 Carondelet Avenue St. Louis MO
Fully refundableReserve now, pay when you stay
CA $128
CA $149 total
Aug 30 - Aug 31
includes taxes & fees
Hollywood Casino & Hotel St. Louis
777 Casino Center Drive Maryland Heights MO
Fully refundableReserve now, pay when you stay
CA $139
CA $204 total
Sep 8 - Sep 9
includes taxes & fees
8.6/10 Excellent! (2,204 reviews)
"We saw a concert at the amphitheater and spent the night there. Had late night pizza and cookies afterwards at the daiquiri place. Good experience."
Reviewed on Aug 8, 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.
What to do in Madison
St. Louis Ghost Tour: Sinister Sins & Shadows
CA $34
per adult
100% of travellers recommend
StL's Signature "Sights and Bites" - Private Tour in St. Louis
CA $246
per adult
Lemp Haunted Neighborhood Walking Tour
CA $35
per adult
84% of travellers recommend
Frequently asked questions
How much does a Madison vacation package cost?
Offering great value package deals from CA $1,030 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?
- 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.
- 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.
- 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.
- 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.
