Madison Vacations from $288

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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.
Hotel 24 South

Hotel 24 South

3 out of 5
Price was $335, price is now $288 per person
$288
per person
Jun 13 - Jun 15
found 11 hours ago
Roundtrip flight included
New York (NYC) to Weyers Cave (SHD)
9.6/10 Exceptional! (1,120 reviews)
We did not use either of these services on this trip.

Reviewed on May 14, 2026

Little Mod Hotel at the University

Little Mod Hotel at the University

3 out of 5
Venable
Price was $402, price is now $302 per person
$302
per person
Jun 13 - Jun 15
found 11 hours ago
Roundtrip flight included
New York (NYC) to Charlottesville (CHO)
9.2/10 Wonderful! (331 reviews)
Super clean, great room, one of the best places I have stayed. It was however quite loud. Sound carried through the walls and ceilings and from across the street. The hotel does supply earbuds, a white noise machine, and a record player with an amazing selection of records. Hotel is well located and can be walked to from anywhere downtown. Lots of good food in the area as well!

Reviewed on May 13, 2026

Virginia Guesthouse Hotel

Virginia Guesthouse Hotel

2 out of 5
Lewis Mountain
Price was $467, price is now $359 per person
$359
per person
Jun 13 - Jun 15
found 11 hours ago
Roundtrip flight included
New York (NYC) to Charlottesville (CHO)
9/10 Wonderful! (12 reviews)
This hotel is fantastic! Gorgeous design, super friendly staff, perfect location, and great connection to the uva community. The rooms were well appointed with super soft robes and towels. The staff went above and beyond to greet us. We also ate at the main restaurant Poplar and the food, decor and service was perfect! I’m excited to continue to visit this fantastic addition to the uva community!

Reviewed on May 6, 2026

Stable Craft Brewing & Cidery

Stable Craft Brewing & Cidery

2 out of 5
Price was $446, price is now $366 per person
$366
per person
Jul 22 - Jul 25
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Weyers Cave (SHD)
No reviews
Shenandoah Wilderness Traveler

Shenandoah Wilderness Traveler

2 out of 5
Price was $362, price is now $302 per person
$302
per person
Jun 13 - Jun 15
found 11 hours ago
Roundtrip flight included
New York (NYC) to Charlottesville (CHO)
8.8/10 Excellent! (87 reviews)
I loved everything about my stay here; comfortable and clean accommodations, beautiful grounds, an on-site stables with many lovely rescued horses, wonderful restaurant inside the lodge, and a very welcoming and helpful staff. I would definitely love to stay here again one day! Thank you, Shenandoah Wilderness Traveler, for making my stay so enjoyable!

Reviewed on May 4, 2026

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Madison Hotel Deals

The Cabin at the Lake

The Cabin at the Lake

Madison VA
$260 nightly
The price is $286 total per night from May 20 to May 21
$286 total
May 20 - May 21
Total with taxes and fees
9.8/10 Exceptional! (50 reviews)
Great view and access to the lake!

Reviewed on May 11, 2026

The Cabin at the Lake
Old Rag View Horse Farm with Log Lodge and Treehouse

Old Rag View Horse Farm with Log Lodge and Treehouse

Madison VA
9.8/10 Exceptional! (168 reviews)
Amazing place! Comfortably fit everyone, all of the amenities were super nice, and was truly a wonderful experience.

Reviewed on Apr 27, 2026

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Old Rag View Horse Farm with Log Lodge and Treehouse
English Inn of Charlottesville

English Inn of Charlottesville

3 out of 5
2000 Morton Drive Charlottesville VA
$109 nightly
The price is $125 total per night from May 18 to May 19
$125 total
May 18 - May 19
Total with taxes and fees
9.2/10 Wonderful! (2,824 reviews)
Surprisingly cozy and comfortable. Good breakfast. Nice stay

Reviewed on May 14, 2026

English Inn of Charlottesville
See all 1,770 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 $288 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.