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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 $407, price is now $330 per person
$330
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip 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.
Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Price was $546, price is now $401 per person
$401
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
New York (NYC) 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.
Dinsmore Boutique Inn

Dinsmore Boutique Inn

4 out of 5
Price was $586, price is now $433 per person
$433
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
New York (NYC) 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.
The Doyle Hotel

The Doyle Hotel

3.5 out of 5
Price was $521, price is now $396 per person
$396
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
New York (NYC) 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 $510, price is now $398 per person
$398
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
New York (NYC) 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.
Graduate by Hilton Charlottesville

Graduate by Hilton Charlottesville

4 out of 5
Price was $1,214, price is now $970 per person
$970
per person
Mar 26 - Mar 29
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 $466, price is now $385 per person
$385
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
New York (NYC) 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.
The Draftsman, Charlottesville, University, Autograph Collection Hotel

The Draftsman, Charlottesville, University, Autograph Collection Hotel

4 out of 5
Price was $1,332, price is now $1,106 per person
$1,106
per person
Mar 26 - Mar 29
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 room service. Our guests praise the helpful staff in our reviews. Popular attractions Downtown Mall and Monticello are located nearby.

Wintergreen Vacation Packages 3-4 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 $521, price is now $396 per person
$396
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
New York (NYC) to Charlottesville (CHO)
Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Jefferson Park Avenue
Price was $546, price is now $401 per person
$401
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
New York (NYC) to Charlottesville (CHO)
Dinsmore Boutique Inn

Dinsmore Boutique Inn

4 out of 5
Venable
Price was $586, price is now $433 per person
$433
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
New York (NYC) to Charlottesville (CHO)
Little Mod Hotel at the University

Little Mod Hotel at the University

3 out of 5
Venable
Price was $510, price is now $398 per person
$398
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
New York (NYC) to Charlottesville (CHO)

Wintergreen Vacation Packages 5-7 Night Stays

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

Shenandoah Wilderness Traveler

2 out of 5
Price was $692, price is now $570 per person
$570
per person
Feb 14 - Feb 20
found 24 hours ago
Roundtrip non-stop flight included
New York (NYC) to Charlottesville (CHO)
Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Jefferson Park Avenue
Price was $990, price is now $813 per person
$813
per person
Feb 14 - Feb 20
found 24 hours ago
Roundtrip non-stop flight included
New York (NYC) 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 $692, price is now $570 per person
$570
per person
Feb 14 - Feb 20
found 24 hours ago
Roundtrip non-stop flight included
New York (NYC) to Charlottesville (CHO)
Little Mod Hotel at the University

Little Mod Hotel at the University

3 out of 5
Venable
Price was $933, price is now $779 per person
$779
per person
Feb 14 - Feb 20
found 24 hours ago
Roundtrip non-stop flight included
New York (NYC) 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 4 days ago
$284
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Jan 20 from Midway Intl. to Charlottesville-Albemarle, returning Sat, Jan 31, priced at $284 found 4 days ago
Bargain Flight
Sat, Jan 24 - Thu, Jan 29
DFW
Dallas-Fort Worth Intl.
CHO
Charlottesville-Albemarle
$285 Roundtrip, found 7 hours ago
$285
Roundtrip
found 7 hours 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 7 hours ago
Delta
Tue, Jan 27 - Sun, Feb 1
DAL
Love Field
CHO
Charlottesville-Albemarle
$297 Roundtrip, found 3 days ago
$297
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Jan 27 from Love Field to Charlottesville-Albemarle, returning Sun, Feb 1, priced at $297 found 3 days ago
Delta
Sun, Jan 18 - Sun, Jan 25
ORD
O'Hare Intl.
CHO
Charlottesville-Albemarle
$307 Roundtrip, found 4 days ago
$307
Roundtrip
found 4 days ago
Select Delta flight, departing Sun, Jan 18 from O'Hare Intl. to Charlottesville-Albemarle, returning Sun, Jan 25, priced at $307 found 4 days ago