Search Deals onCumberland Vacation Packages
Cumberland Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Shenandoah Wilderness Traveler
Price was $734, price is now $597 per person
$597
per person
Oct 14 - Oct 18
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.
Good
Reviewed on Sep 9, 2026
English Inn of Charlottesville
Price was $786, price is now $690 per person
$690
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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.
Best place to stay
Reviewed on Sep 9, 2026
Boardwalk Hotel on Lake Anna by Kasa
Price was $749, price is now $668 per person
$668
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Charlottesville (CHO)
Stay at this aparthotel in Louisa. Enjoy free WiFi, free parking, and air conditioning. Popular attractions Hunters Landing and Belmont Park are located nearby.
The Estate at Meander
Price was $1,142, price is now $1,061 per person
$1,061
per person
Oct 22 - Oct 25
found 24 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Charlottesville (CHO)
Stay at this B&B in Locust Dale. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Cedar Mountain and Rapidian Historic District are located nearby.
Country Inn & Suites by Radisson, Charlottesville-UVA, VA
Price was $1,521, price is now $1,465 per person
$1,465
per person
Oct 22 - Oct 25
found 24 hours ago
Roundtrip non-stop flight included
Chicago (ORD) 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 helpful staff in our reviews. Popular attractions John Paul Jones Arena and Downtown Mall are located nearby.
Cumberland Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Fri, Sep 25 - Mon, Sep 28
MCO
Orlando Intl.
RIC
Richmond Intl.
$196 Roundtrip, found 2 days ago
$196
Roundtrip
found 2 days ago
Wed, Nov 11 - Sun, Nov 15
BOS
Logan Intl.
RIC
Richmond Intl.
$213 Roundtrip, found 3 days ago
$213
Roundtrip
found 3 days ago
Wed, Sep 16 - Wed, Sep 23
LGA
LaGuardia
CHO
Charlottesville-Albemarle
$242 Roundtrip, found 4 days ago
$242
Roundtrip
found 4 days ago
Wed, Nov 4 - Tue, Nov 10
FLL
Fort Lauderdale - Hollywood Intl.
RIC
Richmond Intl.
$243 Roundtrip, found 4 hours ago
$243
Roundtrip
found 4 hours ago
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