Madison Vacation Packages

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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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Your Madison Vacation

Book a tailored Madison vacation package that includes everything you need and nothing you don't. Good for culture, history and bars and pubs, think about staying in the neighborhood of Greater Belhaven. A trip to Madison is an ideal opportunity to go sightseeing. Be sure to visit popular attractions like Tougaloo College, Annandale Golf Club and Mississippi Crafts Center. Your perfect Madison vacation is a few clicks away. Browse hotels, airfares and more on Expedia for a trip that's tailored to suit your travel style.

Top Madison Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Jackson

Hilton Jackson

3.5 out of 5
Price was CA $705, price is now CA $603 per person
CA $603
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Jackson (JAN)
7.6/10 Good! (1,010 reviews)
The only good things about that hotel is the staff and the lobby. The rooms and the elevator are dirty.

Reviewed on Jul 9, 2026

The Westin Jackson

The Westin Jackson

4 out of 5
Downtown Jackson
Price was CA $919, price is now CA $820 per person
CA $820
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Jackson (JAN)
9/10 Wonderful! (944 reviews)
We never received housekeeping service and after several requests, they brought us fresh towels and emptied the trash. The front desk staff didn't seem the least bit concerned and offered no apology.

Reviewed on Jul 8, 2026

Wingate by Wyndham Jackson/Ridgeland

Wingate by Wyndham Jackson/Ridgeland

3 out of 5
Price was CA $735, price is now CA $665 per person
CA $665
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Jackson (JAN)
7.6/10 Good! (1,003 reviews)
Love the clean environment and all the employees were so nice and helpful.Quiet at night sleep like a baby .We love everything will stay in the future if go that way

Reviewed on Jul 10, 2026

Best Western Plus Jackson Downtown Coliseum

Best Western Plus Jackson Downtown Coliseum

2.5 out of 5
Greater Belhaven
Price was CA $680, price is now CA $623 per person
CA $623
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Jackson (JAN)
7.8/10 Good! (948 reviews)
Our toilet wouldn't flush in the room so we had to switch to a new room. The rooms were pretty clean but bathroom and hallways were not good. Hallway carpets were very dirty and the whole place smelled a little. Im glad there was gated parking because the area was a little weird.

Reviewed on Jul 8, 2026

Staybridge Suites Jackson by IHG

Staybridge Suites Jackson by IHG

3 out of 5
Price was CA $672, price is now CA $619 per person
CA $619
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Jackson (JAN)
8.6/10 Excellent! (1,006 reviews)
Air conditioner did not work in the room. There were used towels still hung behind the bathroom door. The pool was not very clean either.

Reviewed on Jul 11, 2026

Ready to book your vacation to Madison?

 

Choose your dates

Madison Hotel Deals

Hilton Garden Inn Jackson/Madison

Hilton Garden Inn Jackson/Madison

4 out of 5
320 New Mannsdale Rd Madison MS
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from Jul 18 to Jul 19
CA $173
CA $185 total
Jul 18 - Jul 19
includes taxes & fees
9/10 Wonderful! (1,011 reviews)
"Staff"

Reviewed on Jul 9, 2026

Hilton Garden Inn Jackson/Madison
Courtyard by Marriott Jackson Madison

Courtyard by Marriott Jackson Madison

3 out of 5
601 Baptist Drive Madison MS
The price is CA $179 per night from Jul 18 to Jul 19
CA $179
CA $192 total
Jul 18 - Jul 19
includes taxes & fees
9.4/10 Exceptional! (672 reviews)
"The property was well-kept and in a good location. The staff was friendly and courteous. Would definitely stay again. They do not have free breakfast"

Reviewed on Jul 10, 2026

Courtyard by Marriott Jackson Madison
Baymont by Wyndham Jackson/Ridgeland

Baymont by Wyndham Jackson/Ridgeland

3.5 out of 5
5709 I 55 N Jackson MS
Fully refundableReserve now, pay when you stay
The price is CA $108 per night from Aug 3 to Aug 4
CA $108
CA $122 total
Aug 3 - Aug 4
includes taxes & fees
8/10 Very good! (1,330 reviews)
"Nice place to stay!"

Reviewed on Jul 11, 2026

Baymont by Wyndham Jackson/Ridgeland
See all 497 properties in Madison
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Madison attractions

Reservoir Overlook

Explore the great outdoors at Reservoir Overlook, a lovely green space in Madison. Visit the area's shops, or simply enjoy its restaurants.
See properties

Frequently asked questions

How much does a Madison vacation package cost?
You'll find cheap prices from CA $603 on Expedia for your Madison getaway. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Madison costs.
What are the cheapest months to go to Madison?
If you're looking to snag a cheap Madison vacation package, consider travelling in January, February and May. You're likely to find lower rates on flights and hotels during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Madison?
With a well-planned itinerary, you can easily hit the top Madison sights in a handful of days. But if you want to explore off the beaten track 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 a cinch with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget, apply a few filters and browse what's available. You can personalize your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to view the most economical Madison package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Madison vacation as a package?
You can enjoy significant savings on your next Madison retreat by booking a tailored vacation package. Check the "Package" heading, then select your destination and travel dates to view the best hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
How to plan a trip to Madison?

  1. Choose the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to go to Madison.
  2. Plan your budget wisely: On top of the cost of your hotel, you'll need to factor in other expenses too. These include food, flights and transportation. Also, set aside a little extra for unexpected expenses that may arise during your trip to Madison.
  3. Decide how long to go for: Now that you know more about Madison, you can work out the ideal length of your break. Pull together a rough plan and give yourself enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a personalized Madison vacation package.

Explore a world of travel with Expedia

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