Cumberland Vacations from $740

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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.

The Latest Cumberland vacation packages

Price found within the past 48 hours. Click for updated prices.
Lake Pointe Inn

Lake Pointe Inn

3 out of 5
Price was $811, price is now $740 per person
$740
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Hagerstown (HGR)
9.6/10 Exceptional! (164 reviews)
The staff at the property is amazing, very pleasant.

Reviewed on Aug 20, 2025

Lake Love

Lake Love

3.5 out of 5
Price was $3,941, price is now $3,558 per person
$3,558
per person
Oct 17 - Oct 24
found 1 hour ago
Roundtrip non-stop flight included
Springfield (SPI) to Hagerstown (HGR)
No reviews
Misty Creek

Misty Creek

3.5 out of 5
Price was $2,785, price is now $2,549 per person
$2,549
per person
Oct 17 - Oct 24
found 1 hour ago
Roundtrip non-stop flight included
Springfield (SPI) to Hagerstown (HGR)
No reviews
Gone Fish Inn

Gone Fish Inn

4 out of 5
Price was $2,813, price is now $2,576 per person
$2,576
per person
Oct 17 - Oct 24
found 1 hour ago
Roundtrip non-stop flight included
Springfield (SPI) to Hagerstown (HGR)
No reviews
Lucky Bear Lakeside

Lucky Bear Lakeside

4 out of 5
Waterfront Greens
Price was $2,397, price is now $2,199 per person
$2,199
per person
Oct 17 - Oct 24
found 1 hour ago
Roundtrip non-stop flight included
Springfield (SPI) to Hagerstown (HGR)
No reviews
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Discover the most popular places to visit in Cumberland

Downtown Cumberland Historic District

Downtown Cumberland Historic District

4/5(124 reviews)

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

4.5/5(67 reviews)

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

4.5/5(49 reviews)

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

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
$152 nightly
The price is $173 total per night from Sep 28 to Sep 29
$173 total
Sep 28 - Sep 29
Total with taxes and fees
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
$77 nightly
The price is $88 total per night from Sep 16 to Sep 17
$88 total
Sep 16 - Sep 17
Total with taxes and fees
Best Western Braddock Inn
Sleep Inn & Suites Cumberland - LaVale

Sleep Inn & Suites Cumberland - LaVale

2.5 out of 5
13320 Ali Ghan Road NE, Cumberland, MD
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $106 total per night from Sep 14 to Sep 15
$106 total
Sep 14 - Sep 15
Total with taxes and fees
Sleep Inn & Suites Cumberland - LaVale
See all 2,619 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.

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Frequently asked questions

How much does a Cumberland vacation package cost?
You'll find cheap prices from $740 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?
December, January and February are great times to look for cheap Cumberland vacation packages. Traveling in less busy periods means you can generally find better prices on flights and hotels.
How many days is enough for Cumberland?
Allow around 2 days for your Cumberland vacation in order to take in everything that makes this place special. Wander around key neighborhoods, including Bowmans Addition and Mount Savage Junction. Then check out top sights such as Wills Mountain State Park and Western Maryland Railroad Station. With a well-planned itinerary, you'll be kept busy with room for some rest and relaxation too. Want to venture beyond Cumberland? Consider squeezing in a day trip or two.
Is it worth booking a vacation package to Cumberland?
Popular for its culture, history and nature, a Cumberland vacation offers something for everyone. Be sure to visit key sights like Western Maryland Railroad Station and Downtown Cumberland Historic District, and consider renting some wheels for day trips to discover even more.
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. Pick your travel dates: What you plan to do in Cumberland and your preferred season will help you decide when to go.
  2. Set a budget: Factor in expenses like flights, food and transportation when working out how much to set aside for your trip to Cumberland. Then, pick a property that fits your budget, whether that's a wallet-friendly stay or a high-end retreat.
  3. Use our trip planning tool to discover Cumberland: Research every aspect of your trip to Cumberland with this comprehensive planner. Invite your family and friends to collaborate on a group getaway, search for hotels or things to do and make bookings.
  4. Determine how many days away: Start by making a list of all the activities and attractions you want to get to in Cumberland. Then, estimate how long you'll need for each, including any travel time.
  5. Combine your accommodations and airfare: After you've nailed down your trip dates and duration, lock in the ideal Cumberland vacation package for you.
  6. Add on experiences and excursions: Read our dedicated travel guide to find some awesome things to do in Cumberland. Book tickets or make reservations as soon as you can to save time and avoid the hassle of looking for activities when you arrive.

Does Expedia offer Book Now, Pay Later Cumberland vacation packages?
Secure your perfect escape to Cumberland with our Book Now, Pay Later vacations. No need to save like crazy or wait for your next payday — we've teamed up with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans mean you can spread the total cost across 3, 6 or 12 months. With no late payment fees or hidden charges, it's easy to stay on budget and snap up bargains before they disappear.

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Explore a world of travel with Expedia

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