Madison Holidays

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 S$144 per night from 28 Sept to 29 Sept
S$144
28 Sept - 29 Sept
includes taxes & fees
9/10 Wonderful! (2,431 reviews)
"the front desk was so pleasant , and it was perfect location. the breakfast was really good and some of the best grits we ever had. highly recommend"

Reviewed on 25 Aug, 2025

English Inn of Charlottesville
Massanutten Resort

Massanutten Resort

2.5 out of 5
1822 Resort Dr, McGaheysville, VA
The price is S$151 per night from 2 Sept to 3 Sept
S$151
2 Sept - 3 Sept
includes taxes & fees
8/10 Very Good! (912 reviews)
"First night tge guest upstairs had kids on top floor. You could hear everything. Next night they left and the rest of the week was fantastic. You need a month to do all the activities they offer. Reasonably priced and famiky friendly. I cant wait to come back again, now that i learned where everything ..."

Reviewed on 24 Aug, 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 S$119 per night from 11 Sept to 12 Sept
S$119
11 Sept - 12 Sept
includes taxes & fees
9/10 Wonderful! (206 reviews)
Welcoming front desk staff
"The front desk manager for this hotel is very accommodating and helpful, providing cooking essentials for those who are staying for extended times. The rooms are comfortable and clean in this hotel, which is brand new as of a few months. We stayed there overnight in the middle of a cross town ..."

Reviewed on 24 Aug, 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.

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.