Madison Trips (flight + hotel)

Photo by Phil Martin

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Top hotels in Madison

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 P4,985 per night from Jul 22 to Jul 23
P4,985
P5,894 total
Jul 22 - Jul 23
includes taxes & fees
9/10 Wonderful! (2,264 reviews)
"Clean hotel, friendly staff. Quiet. Great free breakfast! Highly recommend."

Reviewed on Jun 20, 2025

English Inn of Charlottesville
Massanutten Resort
Massanutten Resort
2.5 out of 5
1822 Resort Dr, McGaheysville, VA
The price is P5,917 per night from Jun 24 to Jun 25
P5,917
P7,914 total
Jun 24 - Jun 25
includes taxes & fees
8/10 Very Good! (776 reviews)
"We enjoyed ourselves so much we didn’t want to leave"

Reviewed on Jun 18, 2025

Massanutten Resort
Days Inn by Wyndham Charlottesville/University Area
Days Inn by Wyndham Charlottesville/University Area
2 out of 5
1610 Emmet St N, Charlottesville, VA
Fully refundableReserve now, pay when you stay
The price is P4,065 per night from Jun 29 to Jun 30
P4,065
P4,646 total
Jun 29 - Jun 30
includes taxes & fees
7.8/10 Good! (1,001 reviews)
"Stayed for an extended weekend for a concert. Great location & easy to get out of the parking lot and turn left or right on to 29 with a red light. Lots of places to eat and shop within minutes. Hotel staff were super friendly and accommodating! Breakfast was good, especially the cheese omlet heated ..."

Reviewed on Jun 12, 2025

Days Inn by Wyndham Charlottesville/University Area
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 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 many days is enough for Madison?
Typically, a handful of days is enough to check out the main attractions during your Madison vacation. 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 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.

What to do in Madison

Charlottesville's Five Vineyards & Wineries Private Tour

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

P54,439
per traveler
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.