Search Deals onWintergreen Vacation Packages
Wintergreen Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Shenandoah Wilderness Traveler
Price was $697, price is now $590 per person
$590
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
San Antonio (SAT) 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.
Amazing place. Great to go with family or friends. Many activities during the day. Amazing views and the cabins were excellent.
Reviewed on Sep 12, 2026
Little Mod Hotel at the University
Save 100% on your flight
Price was $1,191, price is now $726 per person
$726
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
San Antonio (SAT) 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.
English Inn of Charlottesville
Price was $799, price is now $711 per person
$711
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
San Antonio (SAT) to Charlottesville (CHO)
Book a stay at this business-friendly hotel in Charlottesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions John Paul Jones Arena and Downtown Mall are located nearby.
Virginia Guesthouse Hotel
Price was $1,016, price is now $905 per person
$905
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
San Antonio (SAT) 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.
Wintergreen Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Wintergreen 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.
Tue, Sep 29 - Sat, Oct 3
ORD
O'Hare Intl.
SHD
Shenandoah Valley Regional
$309 Roundtrip, found 4 days ago
$309
Roundtrip
found 4 days ago
Mon, Nov 2 - Mon, Nov 9
ORD
O'Hare Intl.
CHO
Charlottesville-Albemarle
$319 Roundtrip, found 1 day ago
$319
Roundtrip
found 1 day ago
Sat, Oct 31 - Wed, Nov 4
IAH
George Bush Intercontinental
CHO
Charlottesville-Albemarle
$321 Roundtrip, found 1 day ago
$321
Roundtrip
found 1 day ago
Wed, Sep 16 - Tue, Sep 22
BOS
Logan Intl.
CHO
Charlottesville-Albemarle
$383 Roundtrip, found 2 hours ago
$383
Roundtrip
found 2 hours ago
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