Madison Vacations from $752

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Your Madison Vacation

When you book a Madison vacation package, it's easy to enjoy your adventure to the fullest. Uncover the best parts of this lively city knowing that everything has been organized in advance. Your trip to Madison wouldn't be complete without exploring some well-known attractions, starting with Riverview Country Club. Browse Expedia's extensive range of travel options and start planning your dream vacation to Madison now.

The Latest Madison vacation packages

Price found within the past 48 hours. Click for updated prices.
Motel 6 Hurricane, WV

Motel 6 Hurricane, WV

2 out of 5
Price was $771, price is now $752 per person
$752
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Charleston (CRW)
6.2/10 (296 reviews)

Studio 6 Suites Hurricane, Wv

Studio 6 Suites Hurricane, Wv

2 out of 5
Price was $837, price is now $789 per person
$789
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Charleston (CRW)
6.4/10 (11 reviews)
Nothing wrong with an old building, but some maintenance is necessary.

Reviewed on Aug 6, 2026

Opossum Creek Retreat

Opossum Creek Retreat

3 out of 5
Price was $1,155, price is now $1,116 per person
$1,116
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Charleston (CRW)
9.6/10 Exceptional! (60 reviews)
Very attentive and friendly host. Amazing little touches that made the stay feel like visiting family property. Beautiful area. Just perfect for a couples weekend away with the dogs.

Reviewed on Nov 2, 2026

Adventures on the Gorge

Adventures on the Gorge

2 out of 5
Price was $856, price is now $828 per person
$828
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Charleston (CRW)
9.4/10 Exceptional! (196 reviews)
Cabin in the woods....what more could you ask. It was quiet and in a beautiful setting. Food in the restaurant was standard bar food but it was hot and tasty. Bar staff was courteous and efficient, even when tasked with a rowdy party of about 20 people. They were loud but respectful and the staff took it in stride. Only spent one night in our travels through the area but would stay again.

Reviewed on Nov 5, 2026

Sleep Inn & Suites Cross Lanes - South Charleston

Sleep Inn & Suites Cross Lanes - South Charleston

2.5 out of 5
Price was $785, price is now $771 per person
$771
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Charleston (CRW)
9.2/10 Wonderful! (1,004 reviews)

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Madison Hotel Deals

Hampton Inn Charleston-Southridge

Hampton Inn Charleston-Southridge

2.5 out of 5
1 Preferred Pl Charleston WV
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $145 total per night from Dec 6 to Dec 7
$145 total
Dec 6 - Dec 7
Total with taxes and fees
Hampton Inn Charleston-Southridge
Best Western Logan Inn

Best Western Logan Inn

2.5 out of 5
47 Central Avenue Chapmanville WV
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $114 total per night from Nov 15 to Nov 16
$114 total
Nov 15 - Nov 16
Total with taxes and fees
Best Western Logan Inn
Holiday Inn Express Suites Charleston by IHG

Holiday Inn Express Suites Charleston by IHG

2.5 out of 5
95 Rhl Blvd Charleston WV
Fully refundable
$99 nightly
The price is $112 total per night from Nov 26 to Nov 27
$112 total
Nov 26 - Nov 27
Total with taxes and fees
Holiday Inn Express Suites Charleston by IHG
See all 69 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.

Find the Best Madison Vacation Packages

Madison Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Yeager Airport (CRW)
Population
2,900

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Frequently asked questions

How much does a Madison vacation package cost?
You'll find cheap prices from $752 on Expedia for your Madison break. However, a range of factors like the length of stay, hotel choice and season will influence how much your vacation to Madison costs.
What are the cheapest months to go to Madison?
December, January and February are great times to search for cheap Madison vacation packages. Opting to travel in less busy periods means you can typically find lower prices on flights and hotels.
How many days is enough for Madison?
Usually, a handful of days is enough to go to the top sights during your Madison vacation. However, if you prefer to have some time to relax or take day tours, think about extending your trip.
How to find the best Madison package deals?
Use Expedia's filters to find some great Madison package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or browse for Madison package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Madison vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and stays separately. Better still, you can customize your Madison trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Madison?
If you've got your Madison vacation dates finalized, book as early as you can to snap up some incredible deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are ideal for impromptu escapes.
Does Expedia offer Book Now, Pay Later Madison vacation packages?
If you're anything like us, you love traveling the world but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Madison break over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.