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Wintergreen Vacation Packages

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Wintergreen Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Bluegreen Vacations Shenandoah Crossing, an Ascend Collection Resort

Bluegreen Vacations Shenandoah Crossing, an Ascend Collection Resort

2.5 out of 5
Price was $797, price is now $627 per person
$627
per person
Feb 24 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Price was $1,088, price is now $787 per person
$787
per person
Feb 24 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Charlottesville (CHO)
Book a stay at this business-friendly hotel in Charlottesville. Enjoy free WiFi, breakfast (surcharge), and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Downtown Mall and Monticello are located nearby.
The Doyle Hotel

The Doyle Hotel

3.5 out of 5
Price was $1,030, price is now $775 per person
$775
per person
Feb 24 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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 Monticello are located nearby.
Little Mod Hotel at the University

Little Mod Hotel at the University

3 out of 5
Price was $1,008, price is now $778 per person
$778
per person
Feb 24 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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 Downtown Mall and Monticello are located nearby.
Dinsmore Boutique Inn

Dinsmore Boutique Inn

4 out of 5
Price was $1,073, price is now $843 per person
$843
per person
Feb 24 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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 Monticello are located nearby.
Graduate by Hilton Charlottesville

Graduate by Hilton Charlottesville

4 out of 5
Price was $1,040, price is now $836 per person
$836
per person
Feb 24 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Charlottesville (CHO)
Stay at this 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 Downtown Mall and Monticello are located nearby.
English Inn of Charlottesville

English Inn of Charlottesville

3 out of 5
Price was $904, price is now $738 per person
$738
per person
Feb 24 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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 Monticello are located nearby.
Inn and Tavern at Meander

Inn and Tavern at Meander

4 out of 5
Price was $1,180, price is now $966 per person
$966
per person
Feb 24 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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.

Wintergreen Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Jefferson Park Avenue
Price was $448, price is now $365 per person
$365
per person
Feb 13 - Feb 16
found 22 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Charlottesville (CHO)
Inn and Tavern at Meander

Inn and Tavern at Meander

4 out of 5
Price was $623, price is now $518 per person
$518
per person
Feb 12 - Feb 16
found 16 hours ago
Roundtrip flight included
New York (LGA) to Charlottesville (CHO)
English Inn of Charlottesville

English Inn of Charlottesville

3 out of 5
The Meadows
Price was $555, price is now $466 per person
$466
per person
Feb 12 - Feb 16
found 16 hours ago
Roundtrip flight included
New York (LGA) to Charlottesville (CHO)
The Doyle Hotel

The Doyle Hotel

3.5 out of 5
Starr Hill
Price was $648, price is now $546 per person
$546
per person
Feb 12 - Feb 16
found 16 hours ago
Roundtrip flight included
New York (LGA) to Charlottesville (CHO)

Wintergreen Vacation Packages 5-7 Night Stays

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 $1,030, price is now $775 per person
$775
per person
Feb 24 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Charlottesville (CHO)
Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Jefferson Park Avenue
Price was $1,088, price is now $787 per person
$787
per person
Feb 24 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Charlottesville (CHO)
Little Mod Hotel at the University

Little Mod Hotel at the University

3 out of 5
Venable
Price was $1,008, price is now $778 per person
$778
per person
Feb 24 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Charlottesville (CHO)
Dinsmore Boutique Inn

Dinsmore Boutique Inn

4 out of 5
Venable
Price was $1,073, price is now $843 per person
$843
per person
Feb 24 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Charlottesville (CHO)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Delta
Tue, Jan 20 - Sat, Jan 31
MDW
Midway Intl.
CHO
Charlottesville-Albemarle
$284 Roundtrip, found 2 days ago
$284
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Jan 20 from Midway Intl. to Charlottesville-Albemarle, returning Sat, Jan 31, priced at $284 found 2 days ago
United
Tue, Jan 20 - Tue, Jan 27
ORD
O'Hare Intl.
CHO
Charlottesville-Albemarle
$284 Roundtrip, found 9 hours ago
$284
Roundtrip
found 9 hours ago
Select United flight, departing Tue, Jan 20 from O'Hare Intl. to Charlottesville-Albemarle, returning Tue, Jan 27, priced at $284 found 9 hours ago
Bargain Flight
Sat, Jan 24 - Thu, Jan 29
DFW
Dallas-Fort Worth Intl.
CHO
Charlottesville-Albemarle
$285 Roundtrip, found 1 day ago
$285
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Sat, Jan 24 from Dallas-Fort Worth Intl. to Charlottesville-Albemarle, returning Thu, Jan 29, priced at $285 found 1 day ago
Delta
Tue, Jan 27 - Sun, Feb 1
DAL
Love Field
CHO
Charlottesville-Albemarle
$297 Roundtrip, found 1 day ago
$297
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jan 27 from Love Field to Charlottesville-Albemarle, returning Sun, Feb 1, priced at $297 found 1 day ago