Cumberland Vacation Packages

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Your Cumberland Vacation

With one of our vacation packages to Cumberland, you'll have endless opportunities for fun and adventure. There's loads to enjoy, including its laid-back lifestyle and family-friendly attractions. A trip to Cumberland is a great opportunity to do some sightseeing. Make sure you visit big-name attractions such as Western Maryland Railroad Station, Downtown Cumberland Historic District and Canal Place. Your perfect Cumberland vacation is only clicks away. Explore hotels, airfares and more on Expedia for a trip that's tailored to suit your travel style.

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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
The price is CA $148 per night from Sep 1 to Sep 2
CA $148
CA $220 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (1,253 reviews)
The perfect getaway
"The pillows are so soft like sleeping on a cloud the food was excellent and the alcohol cocktails were very good can’t wait to get back there for another few nights love the casino"

Reviewed on Jul. 31, 2025

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 CA $110 per night from Aug 10 to Aug 11
CA $110
CA $126 total
Aug 10 - Aug 11
includes taxes & fees
7.8/10 Good! (1,002 reviews)
"Another nice stay. Had a problem with the card key which was quickly taken care of. Highly recommend this hotel."

Reviewed on Aug. 1, 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 CA $110 per night from Aug 10 to Aug 11
CA $110
CA $126 total
Aug 10 - Aug 11
includes taxes & fees
6.8/10 (1,006 reviews)
"Pet friendly"

Reviewed on Aug. 1, 2025

Ramada by Wyndham Cumberland Downtown
See all 2,635 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.
All Inclusive Vacations
All Inclusive Vacations
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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

Country Club Mall

4.5/5(2 reviews)

You can do some window-shopping at Country Club Mall during your visit to Cumberland. Discover the area's mountain views and seek out the biking trails.

Country Club Mall

Frequently asked questions

How much does a Cumberland vacation package cost?
Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a vacation to Cumberland costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Cumberland?
You can typically find reduced prices and greater availability in January, February and March. Browse our cheap Cumberland vacation packages and you could get some great off-season deals.
How many days is enough for Cumberland?
We suggest planning a Cumberland vacation for a minimum of 2 days. This will allow you time to tick off top attractions such as C&O Canal National Historic Park Visitor's Centre and Canal Place, as well as explore neighbourhoods like Bowmans Addition and Mount Savage Junction. You could even squeeze in one or two day trips from Cumberland.
Is it worth booking a vacation package to Cumberland?
Well known for its nature, history and culture, a Cumberland vacation has something for everyone. Be sure to visit major sights like Downtown Cumberland Historic District and C&O Canal National Historic Park Visitor's Centre, and consider renting a car for day trips to experience even more.
How to find the best Cumberland package deals?
Bagging a cheap Cumberland package deal is a breeze with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget range, add some filters and browse what's available. You can personalize your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most economical Cumberland package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Cumberland vacation as a package?
You can enjoy significant savings on your Cumberland escape by booking a customized vacation package. Click on the "Package" heading, then select your travel dates and destination to see the best hotel prices and airfares. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Cumberland?
If you have your Cumberland vacation dates locked in, book early to bag some incredible deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are perfect for quick escapes.
How to plan a trip to Cumberland?

  1. Choose the right time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to travel to Cumberland.
  2. Set your budget: Consider expenses like flights, food and transportation when calculating how much to put aside for your trip to Cumberland. Then, select a hotel that suits your budget, whether that's a low-cost option or a more luxurious retreat.
  3. Work out your trip length: Consider how much time you want to spend exploring Cumberland. Plan your itinerary so you can get to all the activities and attractions you're interested in without rushing.
  4. Bundle your airfare and accommodations: After you've settled on your travel dates and duration, book the ideal Cumberland vacation package for you.

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