Cumberland Holidays

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    Save up to S$1,300 when you book a flight and hotel together*

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Top hotels in Cumberland

Quality Inn Harlan

Quality Inn Harlan

2.5 out of 5
2608 South Highway 421 Harlan KY
Fully refundable
The price is S$127 per night from 6 Dec to 7 Dec
S$127
6 Dec - 7 Dec
includes taxes & fees
Quality Inn Harlan
The Inn at Wise

The Inn at Wise

3 out of 5
110 E Main Street Wise VA
Fully refundableReserve now, pay when you stay
The price is S$149 per night from 3 Dec to 4 Dec
S$149
3 Dec - 4 Dec
includes taxes & fees
9.4/10 Exceptional! (1,003 reviews)
"This is a great place to stay. It is a good location where you can walk to restaurants and shops. It is very clean and quiet. The Staff is friendly and very helpful with any and all questions. I would highly recommend it."

Reviewed on 13 Nov, 2026

The Inn at Wise
Hampton Inn Norton, VA

Hampton Inn Norton, VA

2.5 out of 5
1051 Park Ave SW Norton VA
Fully refundableReserve now, pay when you stay
The price is S$119 per night from 6 Dec to 7 Dec
S$119
6 Dec - 7 Dec
includes taxes & fees
9.4/10 Exceptional! (236 reviews)
"The staff were exceptionally kind!"

Reviewed on 14 Nov, 2026

Hampton Inn Norton, VA
See all 77 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.

Stay near popular Cumberland attractions

Kingdom Come State Park

8.4/10 (13 reviews)
Perched atop Pine Mountain, this Appalachian gem features dramatic sandstone formations like 290-foot Raven Rock. Hike scenic trails to breathtaking overlooks or enjoy tranquil paddle boating on the park's serene lake.
See properties

Frequently asked questions

How much does a Cumberland holiday package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Cumberland costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Cumberland?
If you're looking to snag a cheap Cumberland holiday package, consider travelling in January, February and November. You'll usually find lower prices on hotels and flights during these months — ideal for a budget-friendly getaway.
How many days is enough for Cumberland?
The ideal length for your Cumberland holiday depends on what you'd like to do. Usually, a handful of days to a week will give you plenty of time to go to all the main sights and explore some hidden treasures along the way.
How to find the best Cumberland package deals?
Begin your search for a Cumberland package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply a few filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Cumberland package deal straight away, just tweak 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 off to a flying start.
Is it cheaper to book a Cumberland holiday as a package?
You can enjoy significant savings on your Cumberland retreat by booking a tailored holiday package. Click on the "Package" heading, then select your destination and travel dates to browse the best flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday package to Cumberland?
If you've got your Cumberland travel dates locked in, book as soon as you can to snap up some terrific deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for travelling on a whim.
How to plan a trip to Cumberland?

  1. Choose your travel dates: What you plan to do in Cumberland and your favourite season will help you decide when to travel.
  2. Figure out your budget: Ensure you have enough money to pay for everything from transportation and meals to experiences and flights. Your accommodation will probably be the biggest expense during your trip to Cumberland.
  3. Decide how long to go away for: Now that you know more about Cumberland, you can work out the ideal length of your holiday. Pull together a draft itinerary and give yourself enough time to get through everything on your must-do list.
  4. Combine your airfare and accommodation: Once you've settled on your trip dates and duration, lock in the perfect Cumberland holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.