Cumberland Vacations from $481
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
Boar's Head Resort
Ednam
$610
per person
Dec 11 - Dec 14
found 24 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Charlottesville (CHO)
9/10 Wonderful! (1,004 reviews)
Nice property, rooms need updating
Restaurant a disaster. long waits, ran out of food, food arrived cold and not as clearly stated on menu. Per server "the menu is a little goofy"
Lawn and outside areas had empty glasses, bottles, garbage apparently from prior events.
Reviewed on Sep 22, 2026
Dinsmore Boutique Inn
Venable
$805
per person
Dec 11 - Dec 14
found 24 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Charlottesville (CHO)
9.6/10 Exceptional! (420 reviews)
Jake was very helpful coordinating our check in. The room was very nice and clean. Breakfast at Farm Bell Kitchen was excellent.
Reviewed on Sep 20, 2026
Stay near popular Cumberland attractions
Bear Creek Lake State Park
8.0/10 (6 reviews)
This serene 40-acre lake in Cumberland State Forest offers excellent fishing, swimming, and boating. Hike trails through lush woodlands or unwind at the sandy beach with picturesque water views.
Cumberland Hotel Deals
Private Barndominium Style Lodge on 40 Acres/ Pets/ Fire Pit/River Access
Cumberland VA
Hotel Weyanoke
202 High Street Farmville VA
Fully refundableReserve now, pay when you stay
$103 nightly
$115 total
Oct 19 - Oct 20
Total with taxes and fees
9/10 Wonderful! (1,007 reviews)
"Such a special little spot. Looking forward to staying here again!"
Reviewed on Sep 26, 2026
Crewe Boutique Inn
16092 W Colonial Trail Hwy Crewe VA
Fully refundableReserve now, pay when you stay
$73 nightly
$81 total
Sep 28 - Sep 29
Total with taxes and fees
8.6/10 Excellent! (246 reviews)
"Good overall except for the strong new paint smell in the room"
Reviewed on Sep 26, 2026
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.
Find the Best Cumberland Vacation Packages
Cumberland Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 390 |
Max Temp Winter | 45ºF |
Max Temp Summer | 90ºF |
More vacations you might like
Frequently asked questions
How much does a Cumberland vacation package cost?
You can pick up a vacation package to this top destination from $481 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.
