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

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.
Studio 6 Suites Jackson Ridgeland MS

Studio 6 Suites Jackson Ridgeland MS

3 out of 5
Price was CA $820, price is now CA $750 per person
CA $750
per person
Jan 19 - Jan 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Jackson (JAN)
7.2/10 Good! (751 reviews)

OYO Hotel Jackson South I-55

OYO Hotel Jackson South I-55

2.5 out of 5
Price was CA $871, price is now CA $785 per person
CA $785
per person
Jan 19 - Jan 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Jackson (JAN)
5.2/10 (222 reviews)

Relax Inn

Relax Inn

2 out of 5
Price was CA $819, price is now CA $775 per person
CA $775
per person
Jan 19 - Jan 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Jackson (JAN)
6.8/10 (37 reviews)

Baymont by Wyndham Jackson/Ridgeland

Baymont by Wyndham Jackson/Ridgeland

3.5 out of 5
Price was CA $865, price is now CA $829 per person
CA $829
per person
Jan 19 - Jan 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Jackson (JAN)
8/10 Very good! (1,440 reviews)
Breakfast, quick service and attention

Reviewed on Nov 9, 2026

Wingate by Wyndham Jackson/Ridgeland

Wingate by Wyndham Jackson/Ridgeland

3 out of 5
Price was CA $957, price is now CA $918 per person
CA $918
per person
Jan 19 - Jan 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Jackson (JAN)
7.6/10 Good! (1,004 reviews)

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 $149 per night from Nov 23 to Nov 24
CA $149
CA $160 total
Nov 23 - Nov 24
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
"Perfect overnight stop for our road trip. Madison was as good as other HGI's we have stayed in previously. Great location for us, easy access, footbridge across the lake to more facilities. On this trip for several reasons we were unable to make use of the pool, fitness room, and breakfast options. ..."

Reviewed on Nov 10, 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
Fully refundableReserve now, pay when you stay
The price is CA $179 per night from Nov 22 to Nov 23
CA $179
CA $191 total
Nov 22 - Nov 23
includes taxes & fees
9.4/10 Exceptional! (730 reviews)
"very good"

Reviewed on Nov 9, 2026

Courtyard by Marriott Jackson Madison
Prado Hotel

Prado Hotel

3 out of 5
610 E County Line Road Ridgeland MS
Fully refundableReserve now, pay when you stay
The price is CA $120 per night from Nov 11 to Nov 12
CA $120
CA $132 total
Nov 11 - Nov 12
includes taxes & fees
9/10 Wonderful! (1,461 reviews)
"Decent place to stay but very loud at night"

Reviewed on Nov 10, 2026

Prado Hotel
See all 502 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 $750 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.

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