Cumberland Trips (flight + hotel)

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to P 3,118 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

Top hotels in Cumberland

Rocky Gap Casino & Resort

Rocky Gap Casino & Resort

3 out of 5
16701 Lakeview Road NE, Cumberland, MD
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,254 reviews)
"electric on tv wall didint work"

Reviewed on Aug 5, 2025

Get rates
Rocky Gap Casino & Resort
Best Western Braddock Inn

Best Western Braddock Inn

2.5 out of 5
1268 National Hwy, Cumberland, MD
Fully refundableReserve now, pay when you stay
The price is P4,421 per night from Sep 1 to Sep 2
P4,421
P5,040 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (1,003 reviews)
"While traveling it was a good place to sleep. Appeared clean and well lit."

Reviewed on Aug 5, 2025

Best Western Braddock Inn
Ramada by Wyndham Cumberland Downtown

Ramada by Wyndham Cumberland Downtown

3 out of 5
100 South George Street, Cumberland, MD
Fully refundableReserve now, pay when you stay
The price is P4,513 per night from Sep 1 to Sep 2
P4,513
P5,145 total
Sep 1 - Sep 2
includes taxes & fees
6.8/10 (1,000 reviews)
"This hotel is great if you want to be walking distance to dining and shops in the downtown, as well as historic trails and museums. Staff was friendly. Rooms were average- clean. Bathroom was good, vanity was small in the double queen room. There is a train that runs right behind the hotel- was surprised ..."

Reviewed on Aug 3, 2025

Ramada by Wyndham Cumberland Downtown
See all 2,633 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.

Frequently asked questions

How much does a Cumberland vacation package cost?
You'll find cheap prices on Expedia for your Cumberland break. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Cumberland costs.
What are the cheapest months to go to Cumberland?
If you're hoping to book a cheap Cumberland vacation package, consider traveling in January, February and March. You'll usually find better rates on hotels and airfares during these months — ideal for budget-conscious travelers.
How many days is enough for Cumberland?
We recommend planning a Cumberland vacation for a minimum of 2 days. This gives you enough time to check off top sights such as F. Brooke Whiting House and Museum and Gilchrist Gallery, as well as check out neighborhoods like Bowmans Addition and Mount Savage Junction. You might even be able to fit in a day trip outside of Cumberland.
Is it worth booking a vacation package to Cumberland?
Whether you want to check out top sights such as Downtown Cumberland Historic District and C&O Canal National Historic Park Visitor's Center on your Cumberland vacation, or coming for its excellent nature, history and culture, there's something for everyone here. With so much to experience, you'll soon find out why so many families think Cumberland is a good vacation destination.
How to find the best Cumberland package deals?
Begin your search for a Cumberland package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply 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 big savings. If you don't find the ideal Cumberland package deal right away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Cumberland getaway off to a flying start.
Is it cheaper to book a Cumberland vacation as a package?
You can enjoy significant savings on your next Cumberland getaway by booking a tailored vacation package. Click on the "Package" heading, then enter your travel dates and destination to see some great flight and hotel prices. Bundling can save travelers 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're planning a spontaneous Cumberland vacation, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land amazing deals on your hotels and flights by booking ahead.
How to plan a trip to Cumberland?

  1. Choose when to go: Check your schedule and get packing. Your favorite season and the type of activities available will also help you decide when to vacation in Cumberland.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and meals to airfares and activities. Your hotel will likely be the largest expense during your trip to Cumberland.
  3. Decide your trip length: Think about how much time you want to spend discovering Cumberland. Plan your days so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to find a Cumberland vacation package that brings all your bookings together.

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