Search Deals on
Cumberland Vacation Packages

Build your package with 2 more options

Cumberland Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Charlottesville/University Area

Days Inn by Wyndham Charlottesville/University Area

2 out of 5
Price was $856, price is now $828 per person
$828
per person
Nov 25 - Nov 28
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottesville (CHO)
Book a stay at this business-friendly motel in Charlottesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Downtown Mall and Monticello are located nearby.

Bluegreen Vacations Shenandoah Crossing, an Ascend Collection Resort

Bluegreen Vacations Shenandoah Crossing, an Ascend Collection Resort

2.5 out of 5
Price was $935, price is now $837 per person
$837
per person
Nov 25 - Nov 28
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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.

Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Price was $1,035, price is now $950 per person
$950
per person
Nov 25 - Nov 28
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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 Downtown Mall and Monticello are located nearby.

Little Mod Hotel at the University

Little Mod Hotel at the University

3 out of 5
Price was $984, price is now $904 per person
$904
per person
Nov 25 - Nov 28
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Great Location! Friendly Staff!

Reviewed on Oct 21, 2026

The Doyle Hotel

The Doyle Hotel

3.5 out of 5
Price was $938, price is now $867 per person
$867
per person
Nov 25 - Nov 28
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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 Monticello are located nearby.
The boutique hotel was conveniently located walking distance to the historic downtown area and the aesthetic of the hotel was nice.

Reviewed on Oct 20, 2026

English Inn of Charlottesville

English Inn of Charlottesville

3 out of 5
Price was $973, price is now $924 per person
$924
per person
Nov 25 - Nov 28
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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 Monticello are located nearby.
Good breakfast Hot food needs to be a bit warmer.

Reviewed on Oct 22, 2026

Shenandoah Wilderness Traveler

Shenandoah Wilderness Traveler

2 out of 5
Price was $900, price is now $865 per person
$865
per person
Nov 25 - Nov 28
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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.
The property was much larger than expected and included a lake. Our cabin was tucked in the woods off of a one lane paved road, with good parking spaces. We had a few mosquitoes in our cabin, and also a spider that stayed in its upper corner of the bathroom. The beds and pillows in our two bedroom cabin were very comfortable. Most of the channels on the TV were a little out of focus and we were unable to mirror our phones on the TV, even through we had property internet connected. The breakfast in the main lodge was good and reasonably priced. Prices in the General Store were very reasonable compared to typical resorts. Looking forward to another stay at a future date.

Reviewed on Sep 30, 2026

Country Inn & Suites by Radisson, Charlottesville-UVA, VA

Country Inn & Suites by Radisson, Charlottesville-UVA, VA

3 out of 5
Price was $950, price is now $916 per person
$916
per person
Nov 25 - Nov 28
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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 Downtown Mall and Monticello are located nearby.
Stayed here twice and will stay again Staff all very friendly Very Close to UVA Hospital whice was nice for early morning appointments

Reviewed on Oct 21, 2026

Cumberland Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Bluegreen Vacations Shenandoah Crossing, an Ascend Collection Resort

Bluegreen Vacations Shenandoah Crossing, an Ascend Collection Resort

2.5 out of 5
Price was $935, price is now $837 per person
$837
per person
Nov 25 - Nov 28
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottesville (CHO)
Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Jefferson Park Avenue
Price was $1,035, price is now $950 per person
$950
per person
Nov 25 - Nov 28
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottesville (CHO)
Little Mod Hotel at the University

Little Mod Hotel at the University

3 out of 5
Venable
Price was $984, price is now $904 per person
$904
per person
Nov 25 - Nov 28
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottesville (CHO)
The Doyle Hotel

The Doyle Hotel

3.5 out of 5
Starr Hill
Price was $938, price is now $867 per person
$867
per person
Nov 25 - Nov 28
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottesville (CHO)

Top Flight Deals

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

Frontier Airlines
Wed, Dec 2 - Wed, Dec 16
MCO
Orlando Intl.
RIC
Richmond Intl.
$48 Roundtrip, found 2 hours ago
$48
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Dec 2 from Orlando Intl. to Richmond Intl., returning Wed, Dec 16, priced at $48 found 2 hours ago
Frontier Airlines
Wed, Dec 9 - Wed, Dec 16
DFW
Dallas-Fort Worth Intl.
RIC
Richmond Intl.
$157 Roundtrip, found 2 hours ago
$157
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Dec 9 from Dallas-Fort Worth Intl. to Richmond Intl., returning Wed, Dec 16, priced at $157 found 2 hours ago
Southwest Airlines
Wed, Dec 16 - Mon, Dec 21
FLL
Fort Lauderdale - Hollywood Intl.
RIC
Richmond Intl.
$213 Roundtrip, found 1 day ago
$213
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Dec 16 from Fort Lauderdale - Hollywood Intl. to Richmond Intl., returning Mon, Dec 21, priced at $213 found 1 day ago
Frontier Airlines
Thu, Nov 19 - Wed, Dec 2
EWR
Newark Liberty Intl. Airport
RIC
Richmond Intl.
$214 Roundtrip, found 7 hours ago
$214
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Thu, Nov 19 from Newark Liberty Intl. Airport to Richmond Intl., returning Wed, Dec 2, priced at $214 found 7 hours ago