Madison Vacations from $374
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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.
Shenandoah Wilderness Traveler
Price was $497, price is now $374 per person
$374
per person
Dec 12 - Dec 15
found 20 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Charlottesville (CHO)
8.6/10 Excellent! (59 reviews)
It was a lodge and it was picturesque on water and all around. It was pastures full of beautiful horses. The rooms were really small but they worked and the one thing that I was surprised is when I paid through Expedia I thought I was paid 100% but when I got there, they charge a $25 per day resort fee. Because they also have an RV and cabins and they have a playground basketball court things like that so I guess they charge a resort fee personally it should just be part of the rental so you’re not getting any surprise charges when you get there, otherwise it was lovely and I would actually consider going back there.
Reviewed on Oct 21, 2025
Oakhurst Inn at the University
Jefferson Park Avenue
Price was $647, price is now $473 per person
$473
per person
Dec 12 - Dec 15
found 20 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Charlottesville (CHO)
9.2/10 Wonderful! (496 reviews)
Such a cool venue with excellent service. You can't beat the location if you are coming for anything with UVA! The staff, parking, atmosphere, pool area, live entertainment - all exceptional. I will stay again on my next visit!
Reviewed on Oct 21, 2025
The Doyle Hotel
Starr Hill
Price was $561, price is now $418 per person
$418
per person
Dec 12 - Dec 15
found 20 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Charlottesville (CHO)
8.6/10 Excellent! (926 reviews)
The property was a very cute boutique style hotel. Loved the lobby and the artwork and style aesthetic. Nice rooftop fire pit setup. Beds were very comfortable. Very quiet stay.
Reviewed on Oct 17, 2025
Little Mod Hotel at the University
Venable
Price was $600, price is now $448 per person
$448
per person
Dec 12 - Dec 15
found 20 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Charlottesville (CHO)
9.2/10 Wonderful! (269 reviews)
The place looked really cute, but nothing in the room seemed to actually work! The TV wouldn’t connect to the hotel’s WIFI, and there was no one at the front desk to ask for help. The shower also wasn’t draining properly, so we had to stand in a pool of water while we showered. The record player also didn’t work properly. Any time we needed front staff beyond checking in, no one was there despite being told there would be. Oh yeah, and we woke up in the middle of the night to the loudest train noises!! It literally sounded like we were on top of the train. The place was very cute it just wasn’t very functional and there was no one to go to for help.
Reviewed on Oct 21, 2025
Dinsmore Boutique Inn
Venable
Price was $671, price is now $504 per person
$504
per person
Dec 12 - Dec 15
found 20 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Charlottesville (CHO)
9.6/10 Exceptional! (313 reviews)
Hospitality was awesome. Very relaxing. Great choice
Reviewed on Oct 13, 2025
What to do in Madison
Shenandoah National Park Self-Guided Driving Audio Tour
$17
per traveler
100% of travellers recommend
Madison Hotel Deals
English Inn of Charlottesville
2000 Morton Drive, Charlottesville, VA
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $109 total per night from Nov 5 to Nov 6
$109 total
Nov 5 - Nov 6
Total with taxes and fees
9/10 Wonderful! (2,553 reviews)
It was dated but very comfortable and a great breakfast.
Reviewed on Oct 20, 2025
Massanutten Resort
1822 Resort Dr, McGaheysville, VA
$122 nightly
The price is $135 total per night from Oct 27 to Oct 28
$135 total
Oct 27 - Oct 28
Total with taxes and fees
7.8/10 Good! (1,053 reviews)
Quiet, comfortable, clean condo unit and friendly staff. Has a convenient store and close to a gasoline station. 20 mins drive to Swift run gap entrance of Shenandoah NP. 35 mins drive to Luray Caverns.
Reviewed on Oct 22, 2025
Extended Stay America Premier Suites - Charlottesville
3400 Berkmar Drive, Charlottesville, VA
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $100 total per night from Nov 2 to Nov 3
$100 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (314 reviews)
Clean room, helpful staff and good coffee. I would stay again!
Reviewed on Oct 19, 2025
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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