Cumberland Flight + Hotel Packages

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

Bluegreen Vacations Shenandoah Crossing, an Ascend Collection Resort

$848

per person

Dec 23 - Dec 27

found 1 day ago

Roundtrip non-stop flight included

Houston (IAH) 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.

Little Mod Hotel at the University

$929

per person

Dec 23 - Dec 27

found 1 day 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 Scott Stadium and Downtown Mall are located nearby.

Cute, clean, close the the Corner

Reviewed on Nov 14, 2026

Oakhurst Inn at the University

$991

per person

Dec 23 - Dec 27

found 1 day 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 Scott Stadium and Downtown Mall are located nearby.

The hospitality started before we got there when the staff texted me to see when we were arriving and to help us plan our stay. Great customer service!!!

Reviewed on Nov 13, 2026

The Doyle Hotel

$873

per person

Dec 23 - Dec 27

found 1 day ago

Roundtrip non-stop flight included

Houston (IAH) 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.

Virginia Guesthouse Hotel

$982

per person

Dec 23 - Dec 27

found 1 day 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 Downtown Mall and Monticello are located nearby.

Omni Charlottesville Hotel

$1,001

per person

Dec 23 - Dec 27

found 1 day ago

Roundtrip non-stop flight included

Houston (IAH) 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

$901

per person

Dec 23 - Dec 27

found 1 day ago

Roundtrip non-stop flight included

Houston (IAH) 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.

Foxfield Inn

$1,255

per person

Dec 23 - Dec 27

found 1 day ago

Roundtrip non-stop flight included

Houston (IAH) to Charlottesville (CHO)

Book a stay at this luxury B&B in Charlottesville. Enjoy free breakfast, free parking, and daily housekeeping. Popular attractions Scott Stadium and Birdwood Golf Course are located nearby.

Our favorite stay of our trip. The Rose Room was comfortable with a huge soaking tub and breakfasts were delicious

Reviewed on Oct 28, 2026

Cumberland Vacation Packages 3-4 Night Stays

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