Cumberland Vacations from $768

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.

The Latest Cumberland vacation packages

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 $943, price is now $768 per person
$768
per person
Oct 1 - Oct 6
found 6 hours ago
Roundtrip flight included
Colorado Springs (COS) to Charlottesville (CHO)
9.2/10 Wonderful! (2,410 reviews)
Best hotel breakfast set up I’ve ever had.

Reviewed on Aug 27, 2025

Little Mod Hotel at the University

Little Mod Hotel at the University

3 out of 5
Venable
Price was $1,202, price is now $920 per person
$920
per person
Oct 1 - Oct 6
found 6 hours ago
Roundtrip flight included
Colorado Springs (COS) to Charlottesville (CHO)
9.2/10 Wonderful! (245 reviews)
Well decorated, great location and reasonably priced

Reviewed on Aug 22, 2025

DoubleTree by Hilton Hotel Charlottesville

DoubleTree by Hilton Hotel Charlottesville

4 out of 5
Rio
Price was $1,163, price is now $905 per person
$905
per person
Oct 1 - Oct 6
found 6 hours ago
Roundtrip flight included
Colorado Springs (COS) to Charlottesville (CHO)
8/10 Very Good! (1,000 reviews)
We thought it was a very nice hotel.

Reviewed on Aug 26, 2025

Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Jefferson Park Avenue
Price was $1,700, price is now $1,340 per person
$1,340
per person
Oct 1 - Oct 6
found 6 hours ago
Roundtrip flight included
Colorado Springs (COS) to Charlottesville (CHO)
9.2/10 Wonderful! (480 reviews)
The property was nice and not too far from UVA and downtown area

Reviewed on Aug 10, 2025

The Doyle Hotel

The Doyle Hotel

3.5 out of 5
Starr Hill
Price was $1,507, price is now $1,289 per person
$1,289
per person
Oct 1 - Oct 6
found 6 hours ago
Roundtrip flight included
Colorado Springs (COS) to Charlottesville (CHO)
8.6/10 Excellent! (887 reviews)
My recent stay at The Doyle Hotel was nothing short of amazing! The property is stunning, from the beautifully designed interiors to the charming bookstore and the rooftop with incredible views. John Michael was exceptional in guest services—his engaging personality and thoughtful recommendations made the experience even more memorable. Raceme was also wonderful with valet services, ensuring everything went smoothly. Both staff members were kind, professional, and extremely helpful. The only minor challenge was the limited parking in the area, but thanks to Raceme and John Michael, the valet process was as seamless as possible. Overall, an outstanding stay—I look forward to returning!

Reviewed on Aug 18, 2025

Don't see what you're looking for?
See all available trips from Columbus to Cumberland
View all trips

Discover the most popular places to visit in Cumberland

Bear Creek Lake State Park

4/5(2 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.

Bear Creek Lake State Park

Cumberland Hotel Deals

Hotel Weyanoke

Hotel Weyanoke

3.5 out of 5
202 High Street, Farmville, VA
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $119 total per night from Aug 31 to Sep 1
$119 total
Aug 31 - Sep 1
Total with taxes and fees
9.2/10 Wonderful! (1,009 reviews)
Hafer stay
"My 2-day stay was reserved for 8/22-8/24 thru Hotels.com. Concluded my business early, decided to return home Saturday at 7;00 AM, and informed your staff of this at 7:00 AM. Was unable to get any credit for the 2nd night from Hotels.com or your Weyanoke staff. I ask that since you will be paid by ..."

Reviewed on Aug 24, 2025

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
$62 nightly
The price is $70 total per night from Sep 7 to Sep 8
$70 total
Sep 7 - Sep 8
Total with taxes and fees
Days Inn by Wyndham Farmville
Holiday Inn Express & Suites Farmville by IHG

Holiday Inn Express & Suites Farmville by IHG

2.5 out of 5
404 Sunchase Blvd, Farmville, VA
Fully refundable
$132 nightly
The price is $148 total per night from Aug 31 to Sep 1
$148 total
Aug 31 - Sep 1
Total with taxes and fees
9/10 Wonderful! (581 reviews)
"This property was new to me. But I will visit here again."

Reviewed on Aug 24, 2025

Holiday Inn Express & Suites Farmville by IHG
See all 94 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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Cumberland vacation package cost?
You can pick up a vacation package to this top destination from $768 on Expedia. But how much your vacation to Cumberland costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Cumberland?
You can usually find reduced prices and greater availability in November, December and January. Browse our cheap Cumberland vacation packages and you could score some great off-season discounts.
How many days is enough for Cumberland?
With a well-organized itinerary, you can easily hit the top Cumberland attractions in a few days. But if you want to discover lesser-known spots or take day trips, think about booking your Cumberland vacation for longer.
How to find the best Cumberland package deals?
Start your search for a Cumberland package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the ideal Cumberland package deal right away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Cumberland adventure underway.
Is it cheaper to book a Cumberland vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and stays individually. Better still, you can customize your Cumberland trip to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Cumberland?
If you've got your Cumberland travel dates finalized, book as soon as you can to bag some awesome deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are ideal for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Cumberland vacation packages?
Your Cumberland getaway should be an escape from your busy life, not a source of money-related stress. So to allow you more flexibility, we've joined up with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.