Madison Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Phil Martin
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    Better together
    Save up to NZ$616 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

Madison Holiday

Our pick of the best Madison Hotel Deals

Old Rag View Horse Farm with Log Lodge and Treehouse
Old Rag View Horse Farm with Log Lodge and Treehouse
Madison
10/10 Exceptional! (135 reviews)
Groom's parents' haven
"Lovely relaxing week. We were able to host close friends and family all week as well as to have a beautiful outdoor groom's dinner. The caretakers were so friendly and helpful leading up to our stay and throughout our time there!!"

Reviewed on 29 May 2025

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Old Rag View Horse Farm with Log Lodge and Treehouse
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 NZ$170 per night from 27 July to 28 July
NZ$170
27 July - 28 July
includes taxes & fees
9/10 Wonderful! (2,267 reviews)
"Roomy, clean rooms. Great breakfast. Great location."

Reviewed on 26 Jun. 2025

English Inn of Charlottesville
Massanutten Resort
Massanutten Resort
2.5 out of 5
1822 Resort Dr, McGaheysville, VA
The price is NZ$229 per night from 9 July to 10 July
NZ$229
9 July - 10 July
includes taxes & fees
8/10 Very Good! (796 reviews)
"Great location to access Appalachian Trail and National Park. Great food options and the spa was amazing,"

Reviewed on 26 Jun. 2025

Massanutten Resort
See all 1,709 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.

Frequently asked questions

How much does a Madison holiday package cost?
You'll find cheap prices on Expedia for your Madison break. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your holiday to Madison costs.
What are the cheapest months to go to Madison?
The off-season is the best time to head to Madison if you're trying to keep costs down. Another tip for scoring cheap Madison holiday packages? Try to avoid public holidays and any major festivals or events.
How many days is enough for Madison?
Typically, a handful of days is enough to check out the main attractions during your Madison holiday. However, if you'd like to have more time to rest or take day trips, consider extending your itinerary.
How to find the best Madison package deals?
Start your search for a Madison package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Madison package deal straight away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Madison adventure underway.
Is it cheaper to book a Madison holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component individually. And you'll still enjoy the freedom to create a tailored Madison holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Madison?
If you're considering an impromptu Madison adventure, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land incredible deals on your hotels and flights by booking ahead.
How to plan a trip to Madison?

  1. Choose your travel dates: The things you plan to do in Madison and your preferred season will help you decide when to get away.
  2. Figure out your budget: Ensure you have enough money to cover everything from dining out and transportation to flights and activities. Your hotel will probably be the largest expense during your trip to Madison.
  3. Work out your trip length: Think about how much time you'd like to spend exploring Madison. Plan your itinerary so you can get to all the attractions and experiences you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a tailored Madison holiday package.

What to do in Madison

Charlottesville's Five Vineyards & Wineries Private Tour

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

NZ$1,602
per traveller
Charlottesville: Best Vineyards Private Tour (Up to 14 people)
See all activities in Madison
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.