Madison Vacations

Book a Hotel + Flight together to unlock savings

Photo by Phil Martin

  • Plan, book, travel with confidence

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    Better together

    Save up to AED 148 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

Find the Best Madison Vacation Packages

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 AED 350 per night from Sep 22 to Sep 23
AED 350
AED 412 total
22 Sep - 23 Sep
includes taxes & fees
9/10 Wonderful! (2,415 reviews)
Great clean hotel
"Very nice and clean hotel. Breakfast was good and plentiful."

Reviewed on 21 August 2025

English Inn of Charlottesville
Massanutten Resort

Massanutten Resort

2.5 out of 5
1822 Resort Dr, McGaheysville, VA
The price is AED 309 per night from Sep 7 to Sep 8
AED 309
AED 430 total
7 Sep - 8 Sep
includes taxes & fees
8/10 Very Good! (898 reviews)
"Everything about the place was nice."

Reviewed on 19 August 2025

Massanutten Resort
Extended Stay America Premier Suites - Charlottesville

Extended Stay America Premier Suites - Charlottesville

2.5 out of 5
3400 Berkmar Drive, Charlottesville, VA
Fully refundableReserve now, pay when you stay
The price is AED 288 per night from Aug 24 to Aug 25
AED 288
AED 329 total
24 Aug - 25 Aug
includes taxes & fees
9/10 Wonderful! (199 reviews)
"Great place"

Reviewed on 19 August 2025

Extended Stay America Premier Suites - Charlottesville
See all 1,689 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.

Discover the most popular places to visit in Madison

Early Mountain Vineyards is hands down one of the best in Virginia. It has a wonderful setting with large outside seating area, gas fireplace, live music and incredible view. Owned by AOL founder Steve Case, this vineyard offers tastings of wines from all over Virginia. Try one of their many tasting wine flights!

Early Mountain Vineyards

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.

Early Mountain Vineyards

Frequently asked questions

How much does a Madison vacation 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 vacation 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 vacation packages? Try to avoid public holidays and any major festivals or events.
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 vacation as a package?
Expedia vacation 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 vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation 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 vacation package.