Madison Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
Oakhurst Inn at the University
Jefferson Park Avenue
CA $1,602
per person
Oct 9 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Omaha (OMA) to Charlottesville (CHO)
9.2/10 Wonderful! (593 reviews)
The first room I was in was next to some sort of mechanical room or some very loud machine sound and the floor was vibrating. The staff helped me move to a quieter room, but quiet is relative. It’s old buildings
Reviewed on Aug 11, 2026
Little Mod Hotel at the University
Venable
CA $1,613
per person
Oct 9 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Omaha (OMA) to Charlottesville (CHO)
9.2/10 Wonderful! (360 reviews)
My best friend and I had a great stay! The staff were amazing and kind! The room was clean and loved the theme of the hotel!
Reviewed on Aug 11, 2026
Massanuttens Shenandoah Villas by Tripforth
CA $1,249
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Omaha (OMA) to Weyers Cave (SHD)
7.6/10 Good! (159 reviews)
The rooms were clean and well decorated and the beds were very comfy. It was pretty close to everything so it was convenient.
Reviewed on Aug 12, 2026
Ready to book your vacation to Madison?
Madison Hotel Deals
English Inn of Charlottesville
2000 Morton Drive Charlottesville VA
Fully refundableReserve now, pay when you stay
CA $108
CA $128 total
Sep 10 - Sep 11
includes taxes & fees
Massanutten Resort
1822 Resort Dr McGaheysville VA
CA $121
CA $170 total
Aug 23 - Aug 24
includes taxes & fees
8/10 Very good! (1,481 reviews)
"Everything was as expected with a 4 seasons resort really cool place to take the entire family anytime of year. Highly recommend"
Reviewed on Aug 10, 2026
Country Inn & Suites by Radisson, Charlottesville-UVA, VA
1600 Emmet Street Charlottesville VA
Fully refundable
CA $162
CA $185 total
Aug 23 - Aug 24
includes taxes & fees
9.2/10 Wonderful! (1,208 reviews)
"Établissement très bien aménagé près des services. Personnel extrêmement courtois. Stationnement facile."
Reviewed on Aug 12, 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.
Stay near popular Madison attractions
Early Mountain Vineyards
9.2/10 (24 reviews)
You can enjoy a tasting or tour at Early Mountain Vineyards during your travels to Madison. Discover the mountain views and wineries in this relaxing area.
Madison Plaza
You can enjoy retail therapy at Madison Plaza during your stay in Madison. You can seek out the hiking trails in this family-friendly area.
Madison County Public Library
Madison County Public Library is just one of the places to see in Madison, so why not enjoy the other things to explore during your travels? You can seek out the hiking trails in this family-friendly area.
Lawrence Beasley Park
Explore the great outdoors at Lawrence Beasley Park, a lovely green space in Madison. You can seek out the hiking trails in this family-friendly area.
What to do in Madison
Shenandoah National Park Self-Guided Driving Audio Tour
CA $24
per traveller
100% of travellers recommend
Discover US East Coast Self Guided Audio Tour
CA $204
per traveller
Frequently asked questions
How much does a Madison vacation package cost?
Offering great value package deals from CA $1,166 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?
- 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.
- 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.
- 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.
- 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.
