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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.
Little Mod Hotel at the University

Little Mod Hotel at the University

3 out of 5
Price was $815, price is now $698 per person
$698
per person
Mar 27 - Mar 29
found 1 day ago
Roundtrip flight included
New York (LGA) 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 $952, price is now $771 per person
$771
per person
Mar 27 - Mar 29
found 1 day ago
Roundtrip flight included
New York (LGA) 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.
Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Price was $902, price is now $736 per person
$736
per person
Mar 27 - Mar 29
found 1 day ago
Roundtrip flight included
New York (LGA) 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.
Oasis Near Charlottesville With Pool Grill

Oasis Near Charlottesville With Pool Grill

2 out of 5
Save 100% on your flight
Price was $3,135, price is now $2,618 per person
$2,618
per person
Mar 27 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
New York (LGA) 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.
Kimpton The Forum Hotel by IHG

Kimpton The Forum Hotel by IHG

4 out of 5
Price was $1,259, price is now $1,094 per person
$1,094
per person
Mar 27 - Mar 29
found 1 day ago
Roundtrip flight included
New York (LGA) 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 Downtown Mall and Monticello are located nearby.
Graduate by Hilton Charlottesville

Graduate by Hilton Charlottesville

4 out of 5
Price was $943, price is now $823 per person
$823
per person
Mar 27 - Mar 29
found 1 day ago
Roundtrip flight included
New York (LGA) 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.
Keswick Hall

Keswick Hall

5 out of 5
Price was $1,786, price is now $1,563 per person
$1,563
per person
Mar 27 - Mar 29
found 1 day ago
Roundtrip flight included
New York (LGA) to Charlottesville (CHO)
Book a stay at this luxury hotel in Keswick. Enjoy 2 outdoor pools, a full-service spa, and a golf course. Popular attractions Monticello and Arcady Vineyard are located nearby.
Stoney Creek Cottage Wintergreen w EV Charger

Stoney Creek Cottage Wintergreen w EV Charger

2 out of 5
Price was $967, price is now $852 per person
$852
per person
Mar 27 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
New York (LGA) to Charlottesville (CHO)
Stay at this apartment in Nellysford. Enjoy free parking and a garden. Popular attractions Wintergreen Resort and Stoney Creek Golf Course are located nearby.

Top Flight Deals

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

United
Tue, Mar 10 - Tue, Mar 17
ORD
O'Hare Intl.
CHO
Charlottesville-Albemarle
$204 Roundtrip, found 2 days ago
$204
Roundtrip
found 2 days ago
Select United flight, departing Tue, Mar 10 from O'Hare Intl. to Charlottesville-Albemarle, returning Tue, Mar 17, priced at $204 found 2 days ago
United
Tue, Mar 10 - Sat, Mar 14
MKE
General Mitchell Intl.
CHO
Charlottesville-Albemarle
$275 Roundtrip, found 2 days ago
$275
Roundtrip
found 2 days ago
Select United flight, departing Tue, Mar 10 from General Mitchell Intl. to Charlottesville-Albemarle, returning Sat, Mar 14, priced at $275 found 2 days ago
Delta
Sat, Mar 28 - Wed, Apr 1
ATL
Hartsfield-Jackson Atlanta Intl.
CHO
Charlottesville-Albemarle
$307 Roundtrip, found 2 days ago
$307
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Mar 28 from Hartsfield-Jackson Atlanta Intl. to Charlottesville-Albemarle, returning Wed, Apr 1, priced at $307 found 2 days ago
American Airlines
Sat, Feb 7 - Tue, Feb 10
DEN
Denver Intl.
CHO
Charlottesville-Albemarle
$374 Roundtrip, found 6 days ago
$374
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Feb 7 from Denver Intl. to Charlottesville-Albemarle, returning Tue, Feb 10, priced at $374 found 6 days ago