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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.

Oakhurst Inn at the University
Jefferson Park Avenue
Price was $918, price is now $684 per person
$684
per person
Mar 26 - Mar 29
found 4 hours ago
Roundtrip non-stop flight included
Tampa (TPA) 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

Dinsmore Boutique Inn
Venable
Price was $1,044, price is now $798 per person
$798
per person
Mar 26 - Mar 29
found 4 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Charlottesville (CHO)
9.6/10 Exceptional! (320 reviews)
If you’re looking for a one-of-a-kind place to stay filled with history and charm, this is it. It’s right in the heart of everything UVA, yet it feels like stepping back in time—without giving up any modern comforts.
Jake was incredible to work with—he was flexible with our schedule, made sure we always knew where to go, and communicated better than anyone I’ve worked with before.
Thank you so much for your hospitality. We will definitely stay here again and recommend it to everyone.
Reviewed on Jan 12, 2026

Graduate by Hilton Charlottesville
Venable
Price was $921, price is now $713 per person
$713
per person
Mar 26 - Mar 29
found 4 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Charlottesville (CHO)
8.2/10 Very Good! (1,001 reviews)
Great service,cute place,good location,great for kids,had everything we needed
Reviewed on Dec 16, 2025


Kimpton The Forum Hotel by IHG
UVA
Price was $1,410, price is now $1,124 per person
$1,124
per person
Mar 26 - Mar 29
found 4 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Charlottesville (CHO)
9.6/10 Exceptional! (397 reviews)
Easy check in, warm lobby. Super clean room.
Reviewed on Jan 2, 2026
Madison Hotel Deals

The Cabin at the Lake
Madison VA
$263 nightly
The price is $290 total per night from Jan 19 to Jan 20
$290 total
Jan 19 - Jan 20
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

Massanutten Resort
1822 Resort Dr McGaheysville VA
$130 nightly
The price is $144 total per night from Jan 22 to Jan 23
$144 total
Jan 22 - Jan 23
Total with taxes and fees
8/10 Very Good! (1,193 reviews)
Great facilities & friendly staff! :)
Reviewed on Jan 11, 2026

English Inn of Charlottesville
2000 Morton Drive Charlottesville VA
Fully refundableReserve now, pay when you stay
$96 nightly
The price is $109 total per night from Jan 18 to Jan 19
$109 total
Jan 18 - Jan 19
Total with taxes and fees
9.2/10 Wonderful! (2,699 reviews)
The room had some questionable stains/marks in the bathroom and on the sheets. The front desk lady that checked us in wasn’t the friendliest, but the lady that checked us out was. Otherwise a very nice stay.
Reviewed on Jan 12, 2026
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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