Madison Vacations from $599

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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.
English Inn of Charlottesville

English Inn of Charlottesville

3 out of 5
The Meadows
Price was $744, price is now $599 per person
$599
per person
Sep 4 - Sep 7
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottesville (CHO)
9.2/10 Wonderful! (2,918 reviews)
100% satisfying! Thank you! Oh

Reviewed on Jul 15, 2026

Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Jefferson Park Avenue
Price was $1,951, price is now $1,418 per person
$1,418
per person
Oct 9 - Oct 12
just found
Roundtrip non-stop flight included
Seattle (SEA) to Charlottesville (CHO)
9.2/10 Wonderful! (579 reviews)
Walls were a little thin with noisy night time neighbors. All else really good!

Reviewed on Jul 13, 2026

Little Mod Hotel at the University

Little Mod Hotel at the University

3 out of 5
Venable
Price was $1,701, price is now $1,276 per person
$1,276
per person
Oct 9 - Oct 12
just found
Roundtrip non-stop flight included
Seattle (SEA) to Charlottesville (CHO)
9.2/10 Wonderful! (350 reviews)

The Doyle Hotel

The Doyle Hotel

3.5 out of 5
Starr Hill
Save 100% on your flight
Price was $1,743, price is now $1,329 per person
$1,329
per person
Sep 2 - Sep 8
found 21 hours ago
Roundtrip non-stop flight included
San Diego (SAN) to Charlottesville (CHO)
8.4/10 Very Good! (1,003 reviews)
Unkempt, bath fans dont work, mold on the ceilings near the ice makers, potentially in the duct system. Hard to breathe for my wife with asthma. Transferred rooms around midnight with wife and 2 kids, extreme disturbance lack of rest and refreshment. horrible experience at the hotel,

Reviewed on Jul 14, 2026

Virginia Guesthouse Hotel

Virginia Guesthouse Hotel

3 out of 5
Lewis Mountain
Price was $1,816, price is now $1,530 per person
$1,530
per person
Oct 9 - Oct 12
just found
Roundtrip non-stop flight included
Seattle (SEA) to Charlottesville (CHO)
9.6/10 Exceptional! (44 reviews)
Very nice stay. Comfortable room, good breakfast, reasonable price.

Reviewed on Jul 10, 2026

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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

What to do in Madison

Shenandoah National Park Self-Guided Driving Audio Tour

Shenandoah National Park Self-Guided Driving Audio Tour

$17
per traveler
100% of travellers recommend
Shenandoah National Park Self-Guided Driving Audio Tour
See all activities in Madison

Madison Hotel Deals

Massanutten Resort

Massanutten Resort

2.5 out of 5
1822 Resort Dr McGaheysville VA
$120 nightly
The price is $132 total per night from Aug 9 to Aug 10
$132 total
Aug 9 - Aug 10
Total with taxes and fees
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
$79 nightly
The price is $91 total per night from Aug 10 to Aug 11
$91 total
Aug 10 - Aug 11
Total with taxes and fees
9.2/10 Wonderful! (2,929 reviews)
"100% satisfying! Thank you! Oh"

Reviewed on Jul 15, 2026

English Inn of Charlottesville
Country Inn & Suites by Radisson, Charlottesville-UVA, VA

Country Inn & Suites by Radisson, Charlottesville-UVA, VA

3 out of 5
1600 Emmet Street Charlottesville VA
Fully refundable
$114 nightly
The price is $130 total per night from Aug 9 to Aug 10
$130 total
Aug 9 - Aug 10
Total with taxes and fees
9.2/10 Wonderful! (1,185 reviews)
"great hotel, friendly staff and very clean very clean!!"

Reviewed on Jul 15, 2026

Country Inn & Suites by Radisson, Charlottesville-UVA, VA
See all 1,780 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 $599 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.