Search Deals onMadison Vacation Packages
Madison Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Shenandoah Wilderness Traveler
Price was $639, price is now $591 per person
$591
per person
Dec 17 - Dec 21
found 5 hours ago
Roundtrip flight included
Chicago (ORD) to Charlottesville (CHO)
Stay at this hotel in Gordonsville. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attraction Graves Fine Art Gallery is located nearby.
Well equipped and comfortable lodge. Plenty of activities on site.
Reviewed on Nov 4, 2026
Hotel Madison & Shenandoah Conference Ctr
Price was $918, price is now $796 per person
$796
per person
Dec 23 - Dec 27
found 3 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Weyers Cave (SHD)
Book a stay at this business-friendly hotel in Harrisonburg. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Harrisonburg Farmers Market and Eagle Field at Veterans Memorial Park are located nearby.
Only briefly during our Friday-Sunday stay did we have hot water. The lack of towels, soap, and tissues was also very annoying. I have stayed here a number of times but I was disappointed this time.
Reviewed on Nov 9, 2026
The Blackburn Inn and Conference Center
Price was $852, price is now $746 per person
$746
per person
Dec 23 - Dec 27
found 3 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Weyers Cave (SHD)
Stay at this hotel in Staunton. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Staunton Railroad Station and American Shakespeare Center are located nearby.
Amazing stay. You can feel the history. Staff was awesome. Place was spooky
Reviewed on Nov 9, 2026
Clarion Pointe Harrisonburg
Price was $758, price is now $696 per person
$696
per person
Dec 23 - Dec 27
found 3 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Weyers Cave (SHD)
Book a stay at this golf hotel in Harrisonburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Massanutten Resort and Regal Harrisonburg are located nearby.
Room smelt like mold and wallpaper was coming off the wall. Glad I only stayed
Reviewed on Nov 10, 2026
Afton Mountain Vineyards
Price was $1,511, price is now $1,407 per person
$1,407
per person
Dec 23 - Dec 27
found 3 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Charlottesville (CHO)
Stay at this cabin in Afton. Enjoy free WiFi, free parking, and bathrobes. Popular attractions Afton Mountain Vineyards and Veritas Vineyard and Winery are located nearby.
Hyatt Studios Harrisonburg
Price was $774, price is now $733 per person
$733
per person
Dec 23 - Dec 27
found 3 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Weyers Cave (SHD)
Book a stay at this business-friendly hotel in Harrisonburg. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Massanutten Resort and A Dream Come True Playground are located nearby.
And
Reviewed on Nov 10, 2026
Holiday Inn Staunton Conference Center by IHG
Price was $754, price is now $714 per person
$714
per person
Dec 23 - Dec 27
found 3 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Weyers Cave (SHD)
Book a stay at this golf hotel in Staunton. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Factory Antique Mall and Bertie Murphy Deming Fine Arts Center are located nearby.
The staff was wonderful! My room had some insects in the walls and even in the bathroom. Other than that, it was a nice stay. Plenty of parking and the food downstairs seemed promising. If I stay again, I’d possibly try it.
Reviewed on Nov 10, 2026
Iris Inn and Cabins
Price was $1,383, price is now $1,321 per person
$1,321
per person
Dec 23 - Dec 27
found 3 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Weyers Cave (SHD)
Book a stay at this luxury resort in Waynesboro. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Wildlife Center of Virginia and Shenandoah Valley Art Center are located nearby.
We had a fantastic stay at Iris Inn. Its location is super convenient right off the highway and close to so many hiking trails and wineries. The view from the Inn is enough to not even leave it is so beautiful. We loved the breakfast and ability to have dinner and drinks later in the day.
Reviewed on Nov 1, 2026
Madison Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Mon, Nov 30 - Sat, Dec 5
ORD
O'Hare Intl.
SHD
Shenandoah Valley Regional
$234 Roundtrip, found 16 hours ago
$234
Roundtrip
found 16 hours ago
Mon, Nov 23 - Mon, Nov 30
ATL
Hartsfield-Jackson Atlanta Intl.
CHO
Charlottesville-Albemarle
$257 Roundtrip, found 22 hours ago
$257
Roundtrip
found 22 hours ago
Thu, Jan 14 - Sun, Jan 17
DFW
Dallas-Fort Worth Intl.
CHO
Charlottesville-Albemarle
$289 Roundtrip, found 2 hours ago
$289
Roundtrip
found 2 hours ago
Tue, Nov 17 - Fri, Nov 27
LGA
LaGuardia
CHO
Charlottesville-Albemarle
$306 Roundtrip, found 2 days ago
$306
Roundtrip
found 2 days ago
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