Search Deals onWintergreen Vacation Packages
Wintergreen Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Bluegreen Vacations Shenandoah Crossing, an Ascend Collection Resort
Price was $622, price is now $506 per person
$506
per person
Apr 1 - Apr 5
found 23 hours ago
Roundtrip non-stop flight included
New York (NYC) to Charlottesville (CHO)
Book a stay at this family-friendly hotel in Gordonsville. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attraction Graves Fine Art Gallery is located nearby.
Oasis Near Charlottesville With Pool Grill
Price was $5,285, price is now $4,530 per person
$4,530
per person
Apr 1 - Apr 5
found 7 hours ago
Roundtrip non-stop flight included
New York (NYC) to Charlottesville (CHO)
Stay at this vacation home in Zion Crossroads. Enjoy a garden and bathrobes. Popular attractions Main Beach and The Shoppes at Spring Creek are located nearby.
Wintergreen Retreat Jacuzzi Sauna dog Friendly
Price was $2,155, price is now $1,940 per person
$1,940
per person
Apr 3 - Apr 5
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Charlottesville (CHO)
Stay at this vacation home in Wintergreen. Popular attractions Wintergreen Resort and Raven's Roost Overlook are located nearby.
Mayhurst Inn
Price was $640, price is now $587 per person
$587
per person
Apr 3 - Apr 5
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Charlottesville (CHO)
Stay at this B&B in Orange. Enjoy free breakfast, free WiFi, and free parking. Popular attractions James Madison Museum and The Arts Center in Orange are located nearby.
Sauna dog Friendly Amazing Views to ski Slopes
Price was $1,775, price is now $1,627 per person
$1,627
per person
Apr 3 - Apr 5
found 20 hours ago
Roundtrip non-stop flight included
Norfolk (ORF) to Charlottesville (CHO)
Stay at this apartment in Wintergreen. Enjoy bathrobes. Popular attractions Wintergreen Resort and Raven's Roost Overlook are located nearby.
Inn and Tavern at Meander
Price was $575, price is now $528 per person
$528
per person
Apr 3 - Apr 5
found 22 hours ago
Roundtrip non-stop flight included
New York (NYC) to Charlottesville (CHO)
Stay at this B&B in Locust Dale. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Cedar Mountain and Rapidian Historic District are located nearby.
Residence Inn by Marriott Charlottesville Downtown
Price was $1,353, price is now $1,285 per person
$1,285
per person
Apr 2 - Apr 5
just found
Roundtrip non-stop flight included
Los Angeles (LAX) to Charlottesville (CHO)
Book a stay at this business-friendly hotel in Charlottesville. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Downtown Mall and Monticello are located nearby.
Holiday Inn Express & Suites Charlottesville - Ruckersville by IHG
Price was $569, price is now $554 per person
$554
per person
Apr 3 - Apr 5
found 20 hours ago
Roundtrip non-stop flight included
New York (NYC) to Charlottesville (CHO)
Book a stay at this business-friendly hotel in Barboursville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Preddy Creek Trail Park and Montefalco Vineyard are located nearby.
Wintergreen 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.
Tue, Mar 10 - Tue, Mar 17
ORD
O'Hare Intl.
CHO
Charlottesville-Albemarle
$212 Roundtrip, found 1 day ago
$212
Roundtrip
found 1 day ago
Tue, Mar 10 - Sat, Mar 14
MKE
General Mitchell Intl.
CHO
Charlottesville-Albemarle
$280 Roundtrip, found 2 days ago
$280
Roundtrip
found 2 days ago
Tue, Mar 10 - Mon, Mar 16
DEN
Denver Intl.
CHO
Charlottesville-Albemarle
$321 Roundtrip, found 1 day ago
$321
Roundtrip
found 1 day ago
Tue, Feb 24 - Wed, Mar 4
JFK
John F. Kennedy Intl.
CHO
Charlottesville-Albemarle
$395 Roundtrip, found 1 day ago
$395
Roundtrip
found 1 day ago
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