Madison Vacations from $696

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Your Madison Vacation

History, cuisine, art and more … There's a whole lot to discover with a Madison vacation package. And with the ability to easily customize your city getaway, you know it'll be one that's tough to forget. Early Mountain Vineyards is just one of the must-see attractions to check off your to-do list during a trip to Madison. Your Madison vacation is just a few clicks away. Search flights, hotels and more on Expedia for an adventure that's tailored to suit your travel style.

The Latest Madison vacation packages

Price found within the past 48 hours. Click for updated prices.
Clarion Pointe Harrisonburg

Clarion Pointe Harrisonburg

2.5 out of 5
Price was $758, price is now $696 per person
$696
per person
Dec 23 - Dec 27
found 24 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Weyers Cave (SHD)
8.4/10 Very Good! (1,330 reviews)
Staff were nice, but room smelled too strongly of cleaning products, no coffee maker in room, and lots of items ran out at breakfast.

Reviewed on Nov 11, 2026

Hotel Madison & Shenandoah Conference Ctr

Hotel Madison & Shenandoah Conference Ctr

3.5 out of 5
Price was $918, price is now $796 per person
$796
per person
Dec 23 - Dec 27
found 24 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Weyers Cave (SHD)
9.4/10 Exceptional! (1,229 reviews)
The rooms were nice and quiet. Only stayed one night. Disappointed that the did not have the buffet breakfast.

Reviewed on Nov 10, 2026

The Blackburn Inn and Conference Center

The Blackburn Inn and Conference Center

3.5 out of 5
Price was $852, price is now $746 per person
$746
per person
Dec 23 - Dec 27
found 24 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Weyers Cave (SHD)
9.2/10 Wonderful! (1,004 reviews)
Amazing stay. You can feel the history. Staff was awesome. Place was spooky

Reviewed on Nov 9, 2026

Afton Mountain Vineyards

Afton Mountain Vineyards

3.5 out of 5
Price was $1,511, price is now $1,407 per person
$1,407
per person
Dec 23 - Dec 27
found 24 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Charlottesville (CHO)
7.4/10 Good! (3 reviews)

Hyatt Studios Harrisonburg

Hyatt Studios Harrisonburg

2.5 out of 5
Price was $774, price is now $733 per person
$733
per person
Dec 23 - Dec 27
found 24 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Weyers Cave (SHD)
9/10 Wonderful! (297 reviews)

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Stay near popular Madison attractions

Early Mountain Vineyards

9.2/10 (24 reviews)
Nestled in the Blue Ridge Mountains, Early Mountain Vineyards celebrates Virginia's wine heritage with distinctive tastings. Savor local vintages by the fireplace or enjoy a picnic with panoramic mountain views.
See properties

Madison Hotel Deals

Massanutten Resort

Massanutten Resort

2.5 out of 5
1822 Resort Dr McGaheysville VA
$104 nightly
The price is $114 total per night from Nov 19 to Nov 20
$114 total
Nov 19 - Nov 20
Total with taxes and fees
8/10 Very Good! (1,690 reviews)
"Enjoyed the peacefulness of the stay."

Reviewed on Nov 11, 2026

Massanutten Resort
English Inn of Charlottesville

English Inn of Charlottesville

3 out of 5
2000 Morton Drive Charlottesville VA
Fully refundableReserve now, pay when you stay
$69 nightly
The price is $78 total per night from Dec 7 to Dec 8
$78 total
Dec 7 - Dec 8
Total with taxes and fees
9.2/10 Wonderful! (3,196 reviews)
"Great breakfast. Staff was meh. Nice location. Room was okay."

Reviewed on Nov 11, 2026

English Inn of Charlottesville
Comfort Inn & Suites Charlottesville Hollymead Town Center

Comfort Inn & Suites Charlottesville Hollymead Town Center

2.5 out of 5
1615 Timberwood Blvd Charlottesville VA
Fully refundable
$90 nightly
The price is $103 total per night from Dec 6 to Dec 7
$103 total
Dec 6 - Dec 7
Total with taxes and fees
Comfort Inn & Suites Charlottesville Hollymead Town Center
See all 1,848 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
Charlottesville-Albemarle Airport (CHO)
Population
220
Max Temp Winter
45ºF
Max Temp Summer
85ºF
Top Sights
Early Mountain Vineyards and Rapidan Camp

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Frequently asked questions

How much does a Madison vacation package cost?
You'll find cheap prices from $696 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?
If you'd like to score a cheap Madison vacation package, consider planning a trip in November, December and January. You're likely to find better prices on accommodations and flights during these months — ideal for budget-conscious travelers.
How many days is enough for Madison?
Generally, a handful of days is enough to tick off the major sights during your Madison vacation. However, if you'd like to have more time to chill out or go on day tours, 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.
Does Expedia offer Book Now, Pay Later Madison vacation packages?
Your Madison trip should be a relaxing escape from your busy life, not a reason for money-related stress. So to allow you a little more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.