Madison Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

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

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

Your Madison Vacation

History, cuisine, art and more … There's a whole lot to discover with a Madison vacation package. And with the ability to easily customize your city getaway, you know it'll be one that's tough to forget. Early Mountain Vineyards is just one of the must-see attractions to check off your to-do list during a trip to Madison. Your Madison vacation is just a few clicks away. Search flights, hotels and more on Expedia for an adventure that's tailored to suit your travel style.

Top Madison Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Iris Inn and Cabins

Iris Inn and Cabins

4 out of 5
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Weyers Cave (SHD)
No reviews

Ready to book your vacation to Madison?

 

Choose your dates

Madison Hotel Deals

English Inn of Charlottesville

English Inn of Charlottesville

3 out of 5
2000 Morton Drive, Charlottesville, VA
Fully refundableReserve now, pay when you stay
The price is CA $126 per night from Jul 30 to Jul 31
CA $126
CA $148 total
Jul 30 - Jul 31
includes taxes & fees
9/10 Wonderful! (2,321 reviews)
"Very homely with excellent service."

Reviewed on Jul. 14, 2025

English Inn of Charlottesville
Massanutten Resort

Massanutten Resort

2.5 out of 5
1822 Resort Dr, McGaheysville, VA
The price is CA $136 per night from Aug 10 to Aug 11
CA $136
CA $183 total
Aug 10 - Aug 11
includes taxes & fees
8/10 Very Good! (827 reviews)
"Everything was great."

Reviewed on Jul. 13, 2025

Massanutten Resort
DoubleTree by Hilton Hotel Charlottesville

DoubleTree by Hilton Hotel Charlottesville

4 out of 5
990 Hilton Heights Rd, Charlottesville, VA
Fully refundableReserve now, pay when you stay
The price is CA $134 per night from Jul 22 to Jul 23
CA $134
CA $153 total
Jul 22 - Jul 23
includes taxes & fees
7.8/10 Good! (1,006 reviews)
"Great pool. Breakfast overpriced"

Reviewed on Jul. 13, 2025

DoubleTree by Hilton Hotel Charlottesville
See all 1,714 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

What to do in Madison

Charlottesville's Five Vineyards & Wineries Private Tour

Charlottesville: Best Vineyards Private Tour (Up to 14 people)

CA $1,326
per traveller
Charlottesville: Best Vineyards Private Tour (Up to 14 people)
See all activities in Madison

Frequently asked questions

How much does a Madison vacation package cost?
Offering great value package deals from CA $1,171 on Expedia, you'll be surprised at how little a vacation to Madison costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Madison?
To pick up cheap Madison vacation packages, plan your trip outside of peak periods such as school holidays. You'll generally find better availability and lower prices in the off-season or when it's less busy.
How many days is enough for Madison?
With a well-planned itinerary, you can easily visit the top Madison attractions in a handful of days. But if you want to discover hidden spots or go on day trips, consider booking your Madison vacation for longer.
How to find the best Madison package deals?
Bagging a cheap Madison package deal is a cinch with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, apply some filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Popular locations" and more. Sort 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 travelling on a weekday, when prices are often lower.
Is it cheaper to book a Madison vacation as a package?
You can enjoy significant savings on your Madison break by booking a customized vacation package. Check the "Package" heading, then enter your destination and travel dates to browse the best airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car 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 bag some outstanding deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Madison?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to visit Madison.
  2. Set your budget: Consider costs like flights, transportation and food when working out how much to save for your trip to Madison. Then, select a hotel that fits your budget, whether that's an affordable option or a deluxe retreat.
  3. Decide your trip length: Consider how much time you'd like to spend exploring Madison. Plan your days so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a customized Madison vacation package.

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