Cumberland Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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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.
English Inn of Charlottesville

English Inn of Charlottesville

3 out of 5
The Meadows
Price was CA $1,036, price is now CA $978 per person
CA $978
per person
Sep 10 - Sep 12
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Charlottesville (CHO)
9.2/10 Wonderful! (2,911 reviews)
Everything was good but the Ice machine was not working

Reviewed on Jul 4, 2026

Little Mod Hotel at the University

Little Mod Hotel at the University

3 out of 5
Venable
Price was CA $1,169, price is now CA $1,034 per person
CA $1,034
per person
Sep 10 - Sep 12
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Charlottesville (CHO)
9.2/10 Wonderful! (349 reviews)
This place is so unique and fun!

Reviewed on Jun 30, 2026

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

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

3 out of 5
The Meadows
Price was CA $1,093, price is now CA $1,066 per person
CA $1,066
per person
Sep 10 - Sep 12
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Charlottesville (CHO)
9/10 Wonderful! (1,160 reviews)
This was a very clean, Best Western. The bedding was extremely soft and comfortable. The wait staff was excellent! Highly recommend coming here. It was also right off the expressway

Reviewed on Jul 5, 2026

Ready to book your vacation to Cumberland?

 

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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 $127 per night from Jul 7 to Jul 8
CA $127
CA $159 total
Jul 7 - Jul 8
includes taxes & fees
Hotel Weyanoke
Crewe Boutique Inn

Crewe Boutique Inn

2.5 out of 5
16092 W Colonial Trail Hwy Crewe VA
Fully refundableReserve now, pay when you stay
The price is CA $105 per night from Jul 6 to Jul 7
CA $105
CA $117 total
Jul 6 - Jul 7
includes taxes & fees
8.8/10 Excellent! (215 reviews)
"Everything was great."

Reviewed on Jul 5, 2026

Crewe Boutique Inn
See all 116 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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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 $978 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.