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Wintergreen Resort Vacation Packages

Wintergreen Resort Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Shenandoah Wilderness Traveler

Shenandoah Wilderness Traveler

2 out of 5
Save 100% on your flight
Price was $529, price is now $378 per person
$378
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip flight included
Houston (IAH) 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.
Little Mod Hotel at the University

Little Mod Hotel at the University

3 out of 5
Price was $1,049, price is now $838 per person
$838
per person
Oct 29 - Nov 2
found 16 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.
Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Price was $1,174, price is now $968 per person
$968
per person
Oct 29 - Nov 2
found 16 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.
Bluegreen Vacations Shenandoah Crossing, an Ascend Collection Resort

Bluegreen Vacations Shenandoah Crossing, an Ascend Collection Resort

2.5 out of 5
Price was $733, price is now $605 per person
$605
per person
Oct 29 - Nov 2
found 16 hours ago
Roundtrip flight included
Chicago (ORD) 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.
Super 8 by Wyndham Charlottesville

Super 8 by Wyndham Charlottesville

2 out of 5
Price was $661, price is now $582 per person
$582
per person
Oct 29 - Nov 2
found 16 hours ago
Roundtrip flight included
Chicago (ORD) to Charlottesville (CHO)
Stay at this motel in Charlottesville. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions John Paul Jones Arena and Downtown Mall are located nearby.
Boar's Head Resort

Boar's Head Resort

4 out of 5
Price was $1,205, price is now $1,091 per person
$1,091
per person
Oct 29 - Nov 2
found 16 hours ago
Roundtrip flight included
Chicago (ORD) to Charlottesville (CHO)
Book a stay at this luxury hotel in Charlottesville. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions John Paul Jones Arena and Downtown Mall are located nearby.
Mayhurst Inn

Mayhurst Inn

3.5 out of 5
Price was $1,388, price is now $1,291 per person
$1,291
per person
Oct 29 - Nov 2
found 16 hours ago
Roundtrip flight included
Chicago (ORD) 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.
The Estate at Meander

The Estate at Meander

4 out of 5
Price was $1,113, price is now $1,041 per person
$1,041
per person
Oct 29 - Nov 2
found 16 hours ago
Roundtrip flight included
Chicago (ORD) 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.
Dinsmore Boutique Inn

Dinsmore Boutique Inn

4 out of 5
Price was $1,117, price is now $1,055 per person
$1,055
per person
Oct 29 - Nov 2
found 16 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.
Days Inn by Wyndham Charlottesville/University Area

Days Inn by Wyndham Charlottesville/University Area

2 out of 5
Price was $589, price is now $568 per person
$568
per person
Oct 29 - Nov 2
found 16 hours ago
Roundtrip flight included
Chicago (ORD) to Charlottesville (CHO)
Book a stay at this business-friendly motel in Charlottesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions John Paul Jones Arena and Downtown Mall are located nearby.
Country Inn & Suites by Radisson, Charlottesville-UVA, VA

Country Inn & Suites by Radisson, Charlottesville-UVA, VA

3 out of 5
Price was $750, price is now $735 per person
$735
per person
Oct 29 - Nov 2
found 16 hours ago
Roundtrip flight included
Chicago (ORD) 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 helpful staff in our reviews. Popular attractions John Paul Jones Arena and Downtown Mall are located nearby.
Clarion Pointe Charlottesville

Clarion Pointe Charlottesville

2.5 out of 5
Price was $610, price is now $604 per person
$604
per person
Oct 29 - Nov 2
found 16 hours ago
Roundtrip flight included
Chicago (ORD) 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 helpful staff and the clean rooms in our reviews. Popular attractions John Paul Jones Arena and Downtown Mall are located nearby.

3-4 Night Vacations in Wintergreen Resort

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Charlottesville

Super 8 by Wyndham Charlottesville

2 out of 5
Hydraulic
Price was $661, price is now $582 per person
$582
per person
Oct 29 - Nov 2
found 16 hours ago
Roundtrip flight included
Chicago (ORD) to Charlottesville (CHO)
Little Mod Hotel at the University

Little Mod Hotel at the University

3 out of 5
Venable
Price was $1,049, price is now $838 per person
$838
per person
Oct 29 - Nov 2
found 16 hours ago
Roundtrip flight included
Chicago (ORD) to Charlottesville (CHO)
Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Jefferson Park Avenue
Price was $1,174, price is now $968 per person
$968
per person
Oct 29 - Nov 2
found 16 hours ago
Roundtrip flight included
Chicago (ORD) to Charlottesville (CHO)
Bluegreen Vacations Shenandoah Crossing, an Ascend Collection Resort

Bluegreen Vacations Shenandoah Crossing, an Ascend Collection Resort

2.5 out of 5
Price was $733, price is now $605 per person
$605
per person
Oct 29 - Nov 2
found 16 hours ago
Roundtrip flight included
Chicago (ORD) to Charlottesville (CHO)

Wintergreen Resort Last Minute Hotel Deals

Snug Wintergreen Resort Studio: Ski In & Out!

Snug Wintergreen Resort Studio: Ski In & Out!

3 out of 5
Nellysford VA
Stay at this apartment in Wintergreen. Enjoy free parking and air conditioning. Popular attractions Wintergreen Resort and Raven's Roost Overlook are located ...
Snug Wintergreen Resort Studio: Ski In & Out!
See all 1,100 properties in Wintergreen Resort
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.

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