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Wintergreen Resort Vacation Packages

Wintergreen Resort Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Charlottesville/University Area

Days Inn by Wyndham Charlottesville/University Area

2 out of 5
Price was $552, price is now $519 per person
$519
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Charlottesville (CHO)
Book a stay at this business-friendly motel in Charlottesville. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Downtown Mall and Monticello are located nearby.
Little Mod Hotel at the University

Little Mod Hotel at the University

3 out of 5
Price was $762, price is now $631 per person
$631
per person
Dec 17 - Dec 21
found 1 day 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 Scott Stadium and Downtown Mall are located nearby.
Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Price was $815, price is now $689 per person
$689
per person
Dec 17 - Dec 21
found 1 day 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 Scott Stadium and Downtown Mall are located nearby.
The Doyle Hotel

The Doyle Hotel

3.5 out of 5
Price was $675, price is now $574 per person
$574
per person
Dec 17 - Dec 21
found 1 day 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 Scott Stadium are located nearby.
Omni Charlottesville Hotel

Omni Charlottesville Hotel

4 out of 5
Price was $827, price is now $729 per person
$729
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Charlottesville (CHO)
Book a stay at this business-friendly hotel in Charlottesville. Enjoy an outdoor pool, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Downtown Mall and Monticello are located nearby.
English Inn of Charlottesville

English Inn of Charlottesville

3 out of 5
Price was $656, price is now $591 per person
$591
per person
Dec 17 - Dec 21
found 1 day 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 pool in our reviews. Popular attractions Downtown Mall and Scott Stadium are located nearby.
Shenandoah Wilderness Traveler

Shenandoah Wilderness Traveler

2 out of 5
Price was $639, price is now $590 per person
$590
per person
Dec 17 - Dec 21
found 1 day 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.
Dinsmore Boutique Inn

Dinsmore Boutique Inn

4 out of 5
Price was $1,136, price is now $1,053 per person
$1,053
per person
Dec 17 - Dec 21
found 1 day 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 Scott Stadium and Downtown Mall are located nearby.
Hyatt Place Charlottesville

Hyatt Place Charlottesville

3 out of 5
Price was $658, price is now $626 per person
$626
per person
Dec 17 - Dec 21
found 1 day 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 in our reviews. Popular attractions Downtown Mall and Scott Stadium 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 $637, price is now $607 per person
$607
per person
Dec 17 - Dec 21
found 1 day 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 Downtown Mall and Scott Stadium are located nearby.
Holiday Inn Express & Suites Charlottesville - Ruckersville by IHG

Holiday Inn Express & Suites Charlottesville - Ruckersville by IHG

2.5 out of 5
Price was $576, price is now $562 per person
$562
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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.
Kimpton The Forum Hotel by IHG

Kimpton The Forum Hotel by IHG

4 out of 5
Price was $796, price is now $781 per person
$781
per person
Dec 17 - Dec 21
found 1 day 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 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Scott Stadium and Downtown Mall are located nearby.

3-4 Night Vacations in Wintergreen Resort

Price found within the past 48 hours. Click for updated prices.
The Doyle Hotel

The Doyle Hotel

3.5 out of 5
Starr Hill
Price was $675, price is now $574 per person
$574
per person
Dec 17 - Dec 21
found 1 day 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 $762, price is now $631 per person
$631
per person
Dec 17 - Dec 21
found 1 day 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 $815, price is now $689 per person
$689
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Charlottesville (CHO)
Omni Charlottesville Hotel

Omni Charlottesville Hotel

4 out of 5
North Downtown
Price was $827, price is now $729 per person
$729
per person
Dec 17 - Dec 21
found 1 day 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 1,079 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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