Cumberland Vacations

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Find the Best Cumberland Vacation Packages

Cumberland Hotel Deals

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! (1,257 reviews)
"Could use better pillows otherwise room was great. Would love to see a buffet but not necessary"

Reviewed on 15 August 2025

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Rocky Gap Casino & Resort
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 AED 297 per night from Aug 20 to Aug 21
AED 297
AED 338 total
20 Aug - 21 Aug
includes taxes & fees
6.8/10 (1,003 reviews)
Great choice for Hotels
"It was great and comfortable"

Reviewed on 15 August 2025

Ramada by Wyndham Cumberland Downtown
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 AED 284 per night from Sep 1 to Sep 2
AED 284
AED 324 total
1 Sep - 2 Sep
includes taxes & fees
7.8/10 Good! (1,003 reviews)
"Very accommodating"

Reviewed on 17 August 2025

Best Western Braddock Inn
See all 2,632 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.

Discover the most popular places to visit in Cumberland

Downtown Cumberland Historic District

Downtown Cumberland Historic District

Find out about the history of Cumberland when you spend time at Downtown Cumberland Historic District. Discover the area's mountain views and casinos.

Downtown Cumberland Historic District

Rocky Gap Casino and Golf Course

Enjoy a round of golf in Cumberland at Rocky Gap Casino and Golf Course. While in this family-friendly area, you can savor the top-notch restaurants.

Rocky Gap Casino and Golf Course

Western Maryland Scenic Railroad

You can find out about the history of Cumberland with a visit to Western Maryland Scenic Railroad. Discover the area's mountain views and seek out the biking trails.

Western Maryland Scenic Railroad

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 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.