Madison Vacations from $356

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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.
Bluegreen Vacations Shenandoah Crossing, an Ascend Collection Resort

Bluegreen Vacations Shenandoah Crossing, an Ascend Collection Resort

2.5 out of 5
Price was $438, price is now $356 per person
$356
per person
Feb 19 - Feb 22
found 24 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Charlottesville (CHO)
8.2/10 Very Good! (823 reviews)
The staff was lovely and so were the rooms, the lake and the horses. The restaurant serves tasty food with large portions

Reviewed on Nov 19, 2025

Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Jefferson Park Avenue
Price was $587, price is now $447 per person
$447
per person
Feb 19 - Feb 22
found 24 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Charlottesville (CHO)
9.2/10 Wonderful! (517 reviews)
Our room was clean and the staff was super friendly and courteous. We did hope that our room had a microwave and refrigerator. It makes sense to have that available in every room on the grounds. Guests I’m sure would appreciate it. Please consider doing this. Lastly, we could here noises above us from possibly furniture that wasn’t secure. Footsteps are understandable, but the rattle of something above room 5 was a bit annoying. This is probably an eat fix. Overall the property was safe, clean and convenient.

Reviewed on Jan 1, 2026

Virginia Guesthouse At University Of Virginia

2 out of 5
Lewis Mountain
Price was $1,216, price is now $927 per person
$927
per person
Apr 17 - Apr 19
found 1 day ago
Roundtrip flight included
New York (NYC) to Charlottesville (CHO)
No reviews
Little Mod Hotel at the University

Little Mod Hotel at the University

3 out of 5
Venable
Price was $581, price is now $451 per person
$451
per person
Feb 19 - Feb 22
found 24 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Charlottesville (CHO)
9.2/10 Wonderful! (281 reviews)
The staff at this property is welcoming and helpful - we had a great stay. Parking is easy, the property is well-maintained, and the location is so convenient to the corner, UVA medical facilities, and the university. Highly recommend.

Reviewed on Jan 15, 2026

The Doyle Hotel

The Doyle Hotel

3.5 out of 5
Starr Hill
Price was $551, price is now $432 per person
$432
per person
Feb 19 - Feb 22
found 24 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Charlottesville (CHO)
8.6/10 Excellent! (944 reviews)
This is a beautiful hotel. Would highly recommend.

Reviewed on Jan 11, 2026

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Madison Hotel Deals

The Cabin at the Lake

The Cabin at the Lake

Madison VA
$263 nightly
The price is $290 total per night from Jan 21 to Jan 22
$290 total
Jan 21 - Jan 22
Total with taxes and fees
9.6/10 Exceptional! (45 reviews)
Cozy cabin right on the lake! You can’t get any closer to the water than this. Hoping to stay here again when the weather is warmer so we can go swimming. There is a fire pit right next to the lake, as well as a dock. This stay is perfect for anyone wanting to connect with the outdoors.

Reviewed on Jan 4, 2026

The Cabin at the Lake
Massanutten Resort

Massanutten Resort

2.5 out of 5
1822 Resort Dr McGaheysville VA
$130 nightly
The price is $144 total per night from Jan 28 to Jan 29
$144 total
Jan 28 - Jan 29
Total with taxes and fees
8/10 Very Good! (1,197 reviews)
I would hve liked

Reviewed on Jan 13, 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
$88 nightly
The price is $101 total per night from Feb 16 to Feb 17
$101 total
Feb 16 - Feb 17
Total with taxes and fees
9.2/10 Wonderful! (2,709 reviews)
Wonderful staff

Reviewed on Jan 19, 2026

English Inn of Charlottesville
See all 1,749 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 $356 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.