Orange Flight + Hotel Packages

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

Days Inn by Wyndham Charlottesville/University Area

$511

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

$637

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

$695

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

$587

per person

Dec 11 - Dec 14

just found

Roundtrip non-stop flight included

Denver (DEN) 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.

The Doyle was a classy and wonderful nights stay. The only thing would make it better is onsite parking. Parking across the main road would have been a deal breaker if I had arrived last night. Otherwise, the hotel is wonderful!

Reviewed on Nov 3, 2026

Omni Charlottesville Hotel

$719

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.

Shenandoah Wilderness Traveler

$580

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.

Great time staying there

Reviewed on Nov 3, 2026

English Inn of Charlottesville

$536

per person

Dec 19 - Dec 22

found 7 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) 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.

Dinsmore Boutique Inn

$1,043

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.

Great!

Reviewed on Nov 3, 2026

Orange Vacation Packages 3-4 Night Stays

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