Madison Vacations from $319

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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.
Little Mod Hotel at the University

Little Mod Hotel at the University

3 out of 5
Venable
Price was $434, price is now $319 per person
$319
per person
Jul 10 - Jul 12
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Charlottesville (CHO)
9.2/10 Wonderful! (332 reviews)
Best experience for our 1 night stay. Loved the vibe!!!

Reviewed on May 14, 2026

The Doyle Hotel

The Doyle Hotel

3.5 out of 5
Starr Hill
Price was $470, price is now $354 per person
$354
per person
Jul 10 - Jul 12
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Charlottesville (CHO)
8.4/10 Very Good! (1,010 reviews)
The hotel is beautiful - sleek and chic! Great location and stellar staff. The rooftop bar and restaurant is my favorite place in Charlottesville. (The gluten-free pizza is FANTASTIC!). The rooms are nice, but there was mildew on the shower walls the last 2 times we stayed there. The gym has some broken equipment, but that won't stop us from coming back! The best value in the area.

Reviewed on May 8, 2026

Dinsmore Boutique Inn

Dinsmore Boutique Inn

4 out of 5
Venable
Price was $685, price is now $527 per person
$527
per person
Jul 15 - Jul 18
found 5 hours ago
Roundtrip flight included
New York (NYC) to Charlottesville (CHO)
9.6/10 Exceptional! (383 reviews)
no elevator to 2nd floor room. clean, parking OK and good breakfast

Reviewed on May 16, 2026

Virginia Guesthouse Hotel

Virginia Guesthouse Hotel

2 out of 5
Lewis Mountain
Price was $652, price is now $506 per person
$506
per person
Jun 20 - Jun 23
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Charlottesville (CHO)
9/10 Wonderful! (14 reviews)
I would’ve given this hotel five stars, had I been charged their normal rack rates. It’s brand new, beautiful, and has an extremely friendly and professional staff. Unfortunately, at nearly $1000 per night on graduation weekend, it raises the expectations and the hotel does not meet that price category of property. It’s a clearly cashing in on a captive audience but seems to be a common theme in the area. That said, as long as you avoid the gauging times, this is an excellent hotel near UVA.

Reviewed on May 18, 2026

Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Jefferson Park Avenue
Price was $571, price is now $467 per person
$467
per person
Jul 15 - Jul 18
found 5 hours ago
Roundtrip flight included
New York (NYC) to Charlottesville (CHO)
9.2/10 Wonderful! (561 reviews)
Clean room. Comfortable beds.

Reviewed on May 8, 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 25 to May 26
$286 total
May 25 - May 26
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
English Inn of Charlottesville

English Inn of Charlottesville

3 out of 5
2000 Morton Drive Charlottesville VA
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $123 total per night from May 26 to May 27
$123 total
May 26 - May 27
Total with taxes and fees
9.2/10 Wonderful! (2,832 reviews)
"room's very nice and comfortable Hotel is quiet Staff was very helpful Check in and check out very easy to do Terrific POOL Quite a beautiful building Breakfast buffet excellent"

Reviewed on May 21, 2026

English Inn of Charlottesville
Massanutten Resort

Massanutten Resort

2.5 out of 5
1822 Resort Dr McGaheysville VA
$121 nightly
The price is $133 total per night from May 25 to May 26
$133 total
May 25 - May 26
Total with taxes and fees
8/10 Very Good! (1,325 reviews)
"The property is set in a beautiful mountain setting with great amenities. The rooms are dated and well worn but it is a great value foe the area."

Reviewed on May 21, 2026

Massanutten Resort
See all 1,692 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 $319 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.