Madison Holidays

Photo by Phil Martin

  • Plan, book, travel with confidence

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    Better together

    Save up to S$134 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

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 S$148 per night from 15 Jul to 16 Jul
S$148
15 Jul - 16 Jul
includes taxes & fees
9/10 Wonderful! (2,309 reviews)
good experience
"Room was clean and comfortable ( we had the king deluxe), the pool was good size and refreshing, the breakfast area was in a private large area ."

Reviewed on 10 Jul, 2025

English Inn of Charlottesville
Massanutten Resort
Massanutten Resort
2.5 out of 5
1822 Resort Dr, McGaheysville, VA
The price is S$171 per night from 10 Aug to 11 Aug
S$171
10 Aug - 11 Aug
includes taxes & fees
8/10 Very Good! (822 reviews)
"Amazing"

Reviewed on 10 Jul, 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 S$143 per night from 20 Jul to 21 Jul
S$143
20 Jul - 21 Jul
includes taxes & fees
7.8/10 Good! (1,003 reviews)
"Overall it was nice"

Reviewed on 11 Jul, 2025

DoubleTree by Hilton Hotel Charlottesville
See all 1,715 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.

What to do in Madison

Charlottesville's Five Vineyards & Wineries Private Tour

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

S$1,239
per traveller
Charlottesville: Best Vineyards Private Tour (Up to 14 people)
Appalachian Mountain Scenic Drives: Self-Guided Driving Audio Tour Bundle

Appalachian Mountain Scenic Drives: Self-Guided Driving Audio Tour Bundle

S$43
per traveller
Appalachian Mountain Scenic Drives: Self-Guided Driving Audio Tour Bundle
See all activities in Madison

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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.