Madison Vacations from $481
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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.
Boar's Head Resort
Ednam
$610
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Charlottesville (CHO)
9/10 Wonderful! (1,004 reviews)
Nice property, rooms need updating
Restaurant a disaster. long waits, ran out of food, food arrived cold and not as clearly stated on menu. Per server "the menu is a little goofy"
Lawn and outside areas had empty glasses, bottles, garbage apparently from prior events.
Reviewed on Sep 22, 2026
Dinsmore Boutique Inn
Venable
$805
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Charlottesville (CHO)
9.6/10 Exceptional! (420 reviews)
Jake was very helpful coordinating our check in. The room was very nice and clean. Breakfast at Farm Bell Kitchen was excellent.
Reviewed on Sep 20, 2026
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.
Madison Plaza
You can enjoy retail therapy at Madison Plaza during your stay in Madison. You can seek out the hiking trails in this family-friendly area.
Madison County Public Library
Madison County Public Library: a welcoming community hub with diverse resources and programs. Browse our book collection, use free Wi-Fi, or join reading challenges in this tranquil space for lifelong learning.
Lawrence Beasley Park
Explore the great outdoors at Lawrence Beasley Park, a lovely green space in Madison. You can seek out the hiking trails in this family-friendly area.
Madison Hotel Deals
English Inn of Charlottesville
2000 Morton Drive Charlottesville VA
Fully refundableReserve now, pay when you stay
$94 nightly
$107 total
Oct 18 - Oct 19
Total with taxes and fees
Massanutten Resort
1822 Resort Dr McGaheysville VA
$109 nightly
$120 total
Sep 28 - Sep 29
Total with taxes and fees
Skyland
Skyline Dr Mile 41.7 & 42.5 Luray VA
$176 nightly
$202 total
Sep 29 - Sep 30
Total with taxes and fees
8.8/10 Excellent! (1,004 reviews)
"Clean and will maintained, close to nature"
Reviewed on Sep 26, 2026
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 $481 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.
