Search Deals onShenandoah Vacation Packages
Shenandoah Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Blackburn Inn and Conference Center
Price was $551, price is now $453 per person
$453
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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.
Hotel 24 South
Price was $514, price is now $459 per person
$459
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Weyers Cave (SHD)
Book a stay at this historic hotel in Staunton. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions American Shakespeare Center and R.R. Smith Center for History & Art are located nearby.
Elevator floor was dirty. I told the girl at the front desk. I’m not sure she reported it.
Lovely hotel and great location. Restaurants walking distance. Cute town to visit.
Reviewed on Aug 27, 2026
Virginia Guesthouse Hotel
Price was $1,870, price is now $1,576 per person
$1,576
per person
Oct 18 - Oct 23
found 19 hours ago
Roundtrip flight included
Chicago (ORD) to Charlottesville (CHO)
Stay at this hotel in Charlottesville. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Popular attractions John Paul Jones Arena and Downtown Mall are located nearby.
Very nice place. Great location
Reviewed on Aug 27, 2026
Little Mod Hotel at the University
Price was $1,670, price is now $1,449 per person
$1,449
per person
Oct 18 - Oct 23
found 19 hours ago
Roundtrip flight included
Chicago (ORD) to Charlottesville (CHO)
Stay at this hotel in Charlottesville. Enjoy free WiFi, breakfast (surcharge), and a picnic area. Our guests praise the helpful staff in our reviews. Popular attractions John Paul Jones Arena and Downtown Mall are located nearby.
The Doyle Hotel
Price was $1,738, price is now $1,510 per person
$1,510
per person
Oct 18 - Oct 23
found 19 hours ago
Roundtrip flight included
Chicago (ORD) to Charlottesville (CHO)
Book a stay at this business-friendly hotel in Charlottesville. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Downtown Mall and John Paul Jones Arena are located nearby.
Oakhurst Inn at the University
Price was $1,756, price is now $1,537 per person
$1,537
per person
Oct 18 - Oct 23
found 19 hours ago
Roundtrip flight included
Chicago (ORD) to Charlottesville (CHO)
Book a stay at this business-friendly hotel in Charlottesville. Enjoy free WiFi, breakfast (surcharge), and a sauna. Our guests praise the helpful staff in our reviews. Popular attractions John Paul Jones Arena and Downtown Mall are located nearby.
Omni Charlottesville Hotel
Price was $2,093, price is now $1,853 per person
$1,853
per person
Oct 18 - Oct 23
found 19 hours ago
Roundtrip flight included
Chicago (ORD) to Charlottesville (CHO)
Book a stay at this business-friendly hotel in Charlottesville. Enjoy free parking, an outdoor pool, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Downtown Mall and John Paul Jones Arena are located nearby.
Lovely atrium. Very comfortable rooms. Exceptionally friendly staff. Great value.
Reviewed on Aug 25, 2026
Dinsmore Boutique Inn
Price was $1,722, price is now $1,563 per person
$1,563
per person
Oct 18 - Oct 23
found 19 hours ago
Roundtrip flight included
Chicago (ORD) to Charlottesville (CHO)
Book a stay at this business-friendly B&B in Charlottesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Downtown Mall and John Paul Jones Arena are located nearby.
The hotel was old but in well conditions, the only bad thing was that the first night the AC didn’t work, so it was a really hot night, but then we got a new room, and everything was good!
Reviewed on Aug 24, 2026
Shenandoah Vacation Packages 5-7 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.
Sat, Oct 24 - Sat, Oct 31
IAH
George Bush Intercontinental
CHO
Charlottesville-Albemarle
$305 Roundtrip, found 1 day ago
$305
Roundtrip
found 1 day ago
Wed, Sep 16 - Wed, Sep 23
LGA
LaGuardia
CHO
Charlottesville-Albemarle
$329 Roundtrip, found 2 days ago
$329
Roundtrip
found 2 days ago
Sat, Aug 29 - Tue, Sep 1
EWR
Newark Liberty Intl. Airport
CHO
Charlottesville-Albemarle
$404 Roundtrip, found 4 days ago
$404
Roundtrip
found 4 days ago
Sat, Aug 29 - Thu, Sep 3
JFK
John F. Kennedy Intl.
CHO
Charlottesville-Albemarle
$576 Roundtrip, found 1 day ago
$576
Roundtrip
found 1 day ago
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