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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.
Holiday Inn Charlottesville-Univ Area by IHG

Holiday Inn Charlottesville-Univ Area by IHG

3 out of 5
Price was $967, price is now $928 per person
$928
per person
Oct 9 - Oct 11
found 14 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Charlottesville (CHO)
Book a stay at this business-friendly hotel in Charlottesville. Enjoy free WiFi, free parking, and a fitness center. 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 $1,686, price is now $1,391 per person
$1,391
per person
Oct 9 - Oct 11
found 14 hours ago
Roundtrip non-stop flight included
Houston (IAH) 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.

Little Mod Hotel at the University

Little Mod Hotel at the University

3 out of 5
Price was $1,609, price is now $1,358 per person
$1,358
per person
Oct 9 - Oct 11
found 14 hours ago
Roundtrip non-stop flight included
Houston (IAH) 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.

Virginia Guesthouse Hotel

Virginia Guesthouse Hotel

3 out of 5
Price was $1,461, price is now $1,245 per person
$1,245
per person
Oct 9 - Oct 11
found 14 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Charlottesville (CHO)
Stay at this hotel in Charlottesville. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Popular attractions John Paul Jones Arena and Downtown Mall are located nearby.
Fantastic in all ways!

Reviewed on Aug 24, 2026

English Inn of Charlottesville

English Inn of Charlottesville

3 out of 5
Price was $1,169, price is now $1,034 per person
$1,034
per person
Oct 9 - Oct 11
found 14 hours ago
Roundtrip non-stop flight included
Houston (IAH) 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 John Paul Jones Arena and Downtown Mall are located nearby.

Hampton Inn & Suites Charlottesville-At the University

Hampton Inn & Suites Charlottesville-At the University

2.5 out of 5
Price was $1,733, price is now $1,579 per person
$1,579
per person
Oct 9 - Oct 11
found 14 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Charlottesville (CHO)
Book a stay at this business-friendly hotel in Charlottesville. Enjoy free breakfast, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Downtown Mall and John Paul Jones Arena are located nearby.
Everything was good

Reviewed on Aug 12, 2026

Sleep Inn & Suites Monticello

Sleep Inn & Suites Monticello

2.5 out of 5
Price was $1,062, price is now $1,027 per person
$1,027
per person
Oct 9 - Oct 11
found 14 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Charlottesville (CHO)
Book a stay at this business-friendly hotel in Charlottesville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Downtown Mall and John Paul Jones Arena are located nearby.

Comfort Inn Monticello

Comfort Inn Monticello

2.5 out of 5
Price was $1,064, price is now $1,028 per person
$1,028
per person
Oct 9 - Oct 11
found 14 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Charlottesville (CHO)
Book a stay at this business-friendly hotel in Charlottesville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Monticello and Downtown Mall are located nearby.
Hot breakfast; great value; great location

Reviewed on Aug 25, 2026

Top Flight Deals

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

American Airlines
Tue, Sep 29 - Sat, Oct 3
ORD
O'Hare Intl.
SHD
Shenandoah Valley Regional
$284 Roundtrip, found 6 days ago
$284
Roundtrip
found 6 days ago
Select American Airlines flight, departing Tue, Sep 29 from O'Hare Intl. to Shenandoah Valley Regional, returning Sat, Oct 3, priced at $284 found 6 days ago
United
Sat, Oct 24 - Sat, Oct 31
IAH
George Bush Intercontinental
CHO
Charlottesville-Albemarle
$301 Roundtrip, found 11 hours ago
$301
Roundtrip
found 11 hours ago
Select United flight, departing Sat, Oct 24 from George Bush Intercontinental to Charlottesville-Albemarle, returning Sat, Oct 31, priced at $301 found 11 hours ago
Bargain Flight
Wed, Aug 26 - Tue, Sep 1
LGA
LaGuardia
CHO
Charlottesville-Albemarle
$315 Roundtrip, found 10 hours ago
$315
Roundtrip
found 10 hours ago
Select Bargain Flight flight, departing Wed, Aug 26 from LaGuardia to Charlottesville-Albemarle, returning Tue, Sep 1, priced at $315 found 10 hours ago
United
Thu, Aug 27 - Mon, Aug 31
EWR
Newark Liberty Intl. Airport
CHO
Charlottesville-Albemarle
$379 Roundtrip, found 2 days ago
$379
Roundtrip
found 2 days ago
Select United flight, departing Thu, Aug 27 from Newark Liberty Intl. Airport to Charlottesville-Albemarle, returning Mon, Aug 31, priced at $379 found 2 days ago