Cumberland Vacation Packages

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Your Cumberland Vacation

Take the hassle out of planning your next epic adventure with a Cumberland vacation package. Whether you're here for its art, food, architecture or other highlights, there's an inexhaustible array of experiences to be had. Eager to sightsee? Spend some time enjoying top attractions such as Bear Creek Lake State Park during your trip to Cumberland. Whoever you're escaping with and whatever you want to spend, your dream Cumberland vacation is only clicks away with Expedia.

Top Cumberland Vacation Deals

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

Shenandoah Wilderness Traveler

2 out of 5
Price was CA $1,118, price is now CA $808 per person
CA $808
per person
Oct 1 - Oct 7
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Charlottesville (CHO)
8.8/10 Excellent! (101 reviews)
This was our second time staying here in the last 6 months (last time being in the winter). The outdoor pool/hotub/splash area was not available either time. Also, WIFI continues to be an issue as you must use a MIFI router (upon request) that also does not provide adequate service. Overall, the stay was ok, and proper for a quick weekend recharge, but I couldn’t imagine staying more than a few days with my family.

Reviewed on Jun 28, 2026

Sonesta ES Suites Charlottesville University

Sonesta ES Suites Charlottesville University

3 out of 5
Barracks Road
Price was CA $1,268, price is now CA $1,125 per person
CA $1,125
per person
Oct 1 - Oct 7
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Charlottesville (CHO)
8.8/10 Excellent! (812 reviews)
Overall v good. Only negative was cat smell in room.

Reviewed on Jul 13, 2026

Bluegreen Vacations Shenandoah Crossing, an Ascend Collection Resort

Bluegreen Vacations Shenandoah Crossing, an Ascend Collection Resort

2.5 out of 5
Price was CA $1,023, price is now CA $919 per person
CA $919
per person
Oct 1 - Oct 7
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Charlottesville (CHO)
8.2/10 Very good! (836 reviews)
PERFECT!!!

Reviewed on Jul 14, 2026

Afton Mountain Vineyards

Afton Mountain Vineyards

3 out of 5
Price was CA $2,148, price is now CA $2,100 per person
CA $2,100
per person
Sep 4 - Sep 7
found 2 hours ago
Roundtrip flight included
Halifax (YHZ) to Charlottesville (CHO)
10/10 Exceptional! (2 reviews)
Cozy and comfortable with pond and mountain views. Wine tasting on site and easy access to Wintergreen. We loved our stay and will be back again!

Reviewed on Jan 18, 2026

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Cumberland Hotel Deals

Private Barndominium Style Lodge on 40 Acres/ Pets/ Fire Pit/River Access

Private Barndominium Style Lodge on 40 Acres/ Pets/ Fire Pit/River Access

Cumberland VA
Get rates
Private Barndominium Style Lodge on 40 Acres/ Pets/ Fire Pit/River Access
Hotel Weyanoke

Hotel Weyanoke

3.5 out of 5
202 High Street Farmville VA
Fully refundableReserve now, pay when you stay
The price is CA $155 per night from Jul 16 to Jul 17
CA $155
CA $192 total
Jul 16 - Jul 17
includes taxes & fees
9.2/10 Wonderful! (1,013 reviews)
"Older building, the mattress was terrible woke feeling sore all over. The pillows were the size of sofa cushions, when I notified the front desk asking for larger pillows, I got the lame excuse the the linen closet was locked. Only good thing about this property is the location, other then that its ..."

Reviewed on Jul 11, 2026

Hotel Weyanoke
Days Inn by Wyndham Farmville

Days Inn by Wyndham Farmville

2 out of 5
2015 South Main St. Farmville VA
Fully refundableReserve now, pay when you stay
The price is CA $83 per night from Aug 3 to Aug 4
CA $83
CA $94 total
Aug 3 - Aug 4
includes taxes & fees
7.4/10 Good! (369 reviews)
"The room and the facilities was in disrepair and trashy. It did not offer much other than a bed that was usable. The property itself was as dirty as I have ever seen. This is what Days Inn has unfortunately become. Cheap but nasty"

Reviewed on Jul 5, 2026

Days Inn by Wyndham Farmville
See all 114 properties in Cumberland
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Stay near popular Cumberland attractions

Bear Creek Lake State Park

8.0/10 (6 reviews)
You can take time to visit Bear Creek Lake State Park during your travels to Cumberland. While you're in the area, wander around the natural setting.
See properties

Frequently asked questions

How much does a Cumberland vacation package cost?
You'll find cheap prices from CA $808 on Expedia for your Cumberland break. However, a range of factors like the season, length of stay and your choice of hotel will influence how much your vacation to Cumberland costs.
What are the cheapest months to go to Cumberland?
January, February and November are great times to look for cheap Cumberland vacation packages. Choosing to travel in less busy periods means you'll typically find lower prices on hotels and flights.
How many days is enough for Cumberland?
With a well-organized travel plan, you can easily visit the most popular Cumberland attractions in a few days. But if you want to discover hidden spots or go on day tours, think about booking your Cumberland vacation for longer.
How to find the best Cumberland package deals?
Bagging a cheap Cumberland package deal is easy with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget range, apply some filters and browse what's available. You can fine-tune your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Cumberland package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Cumberland vacation as a package?
You can enjoy significant savings on your Cumberland getaway by booking a personalized vacation package. Check the "Package" heading, then enter your travel dates and destination to view the best hotel prices and airfares. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Cumberland?
If you have your Cumberland travel dates locked in, book early to bag some awesome deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are great for quick escapes.
How to plan a trip to Cumberland?

  1. Choose the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to travel to Cumberland.
  2. Plan your budget wisely: As well as the price of your hotel, you should factor in other expenses. These include transportation, food and flights. Also, set aside some extra funds for unexpected costs that may come up during your trip to Cumberland.
  3. Work out your trip length: Think about how much time you want to spend discovering Cumberland. Plan your itinerary so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a tailored Cumberland vacation package.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.