Madison Vacations from $550

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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.
The Doyle Hotel

The Doyle Hotel

3.5 out of 5
Starr Hill
Price was $661, price is now $550 per person
$550
per person
Aug 7 - Aug 9
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Charlottesville (CHO)
8.4/10 Very Good! (1,009 reviews)
Staff was excellent roof top bar was awesome we will be back!

Reviewed on Jun 24, 2026

Dinsmore Boutique Inn

Dinsmore Boutique Inn

4 out of 5
Venable
Price was $780, price is now $628 per person
$628
per person
Aug 7 - Aug 9
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Charlottesville (CHO)
9.6/10 Exceptional! (398 reviews)
Wow, the architecture, history, the amenities (especially the guest lounge), and breakfast were all outstanding! We will be back.

Reviewed on Jun 26, 2026

Kimpton The Forum Hotel by IHG

Kimpton The Forum Hotel by IHG

4 out of 5
UVA
Price was $675, price is now $568 per person
$568
per person
Aug 7 - Aug 9
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Charlottesville (CHO)
9.6/10 Exceptional! (472 reviews)
Very clean, aesthetically pleasing on the eye, friendly staff. Will return!

Reviewed on Jun 24, 2026

Mayhurst Inn

Mayhurst Inn

3.5 out of 5
Price was $733, price is now $617 per person
$617
per person
Aug 7 - Aug 9
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Charlottesville (CHO)
9.2/10 Wonderful! (293 reviews)
A perfect spot with the delicious breakfast. Highly recommend staying here.

Reviewed on Sep 4, 2025

Virginia Guesthouse Hotel

Virginia Guesthouse Hotel

3 out of 5
Lewis Mountain
Price was $654, price is now $567 per person
$567
per person
Aug 7 - Aug 9
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Charlottesville (CHO)
9.6/10 Exceptional! (37 reviews)
This is a relatively new hotel and it has some growing pains. Check in is easy but establishing a registered car for parking and parking the car and then finding your way back into the hotel are extremely difficult. The rooms are beautiful. The trek from the elevator to the room was quite long. The rooftop bar did not have two of the tap beers on the menu and no cabernet sauvignon. The appetizers in the bar were simply terrible. Especially the "crispy" chick peas that were flavorless and not at all crispy just stale. The staff was very nice and helpful but the parking and the weird food made the total experience just ok.

Reviewed on Jun 28, 2026

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Stay near popular Madison attractions

Early Mountain Vineyards

9.2/5 (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

Madison Hotel Deals

Massanutten Resort

Massanutten Resort

2.5 out of 5
1822 Resort Dr McGaheysville VA
$119 nightly
The price is $132 total per night from Jul 13 to Jul 14
$132 total
Jul 13 - Jul 14
Total with taxes and fees
8/10 Very Good! (1,390 reviews)
"Room was clean facilities were amazing"

Reviewed on Jun 28, 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 Jul 13 to Jul 14
$101 total
Jul 13 - Jul 14
Total with taxes and fees
9.2/10 Wonderful! (2,916 reviews)
"They did not have hair dryer and I forgot mine. Otherwise perfect quiet stay. Will be back"

Reviewed on Jun 28, 2026

English Inn of Charlottesville
Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America

3 out of 5
401 W Main St Luray VA
$114 nightly
The price is $132 total per night from Jul 9 to Jul 10
$132 total
Jul 9 - Jul 10
Total with taxes and fees
9/10 Wonderful! (1,002 reviews)
"A Classic Hotel Wonderfully Staff that is very helpful Close to Luray Caverns"

Reviewed on Jun 28, 2026

Mimslyn Inn Historic Hotels Of America
See all 1,786 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 $550 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.