Cumberland Vacations
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Find the Best Cumberland Vacation Packages
Cumberland Hotel Deals
Rocky Gap Casino & Resort
16701 Lakeview Road NE Cumberland MD
Fully refundableReserve now, pay when you stay
₩138,878
₩208,436 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (1,674 reviews)
"Rooms were clean"
Reviewed on Aug 17, 2026
Ramada by Wyndham Cumberland Downtown
100 South George Street Cumberland MD
Fully refundableReserve now, pay when you stay
₩114,316
₩130,321 total
Sep 7 - Sep 8
includes taxes & fees
7/10 Good! (1,001 reviews)
"Easy clean and polite"
Reviewed on Aug 15, 2026
Sleep Inn & Suites Cumberland - LaVale
13320 Ali Ghan Road NE Cumberland MD
Fully refundable
₩131,163
₩149,526 total
Sep 13 - Sep 14
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
"X"
Reviewed on Aug 17, 2026
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
Photo by Sig
Downtown Cumberland Historic District
8.6/10 (424 reviews)
Stroll through Cumberland's revitalized historic district, where 19th-century architecture frames vibrant local shops. Savor outdoor dining and seasonal festivals in this pedestrian-friendly downtown hub.
Lake Habeeb
9.0/10 (8 reviews)
Lake Habeeb's crystal-clear waters create a stunning blue centerpiece within Rocky Gap State Park. Enjoy premium fishing for bass and trout or hike the scenic Lakeside Loop for breathtaking mountain reflections.
Western Maryland Scenic Railroad
9.0/10 (224 reviews)
Journey through the Allegheny Mountains on a historic steam locomotive while admiring picturesque landscapes. The 4-hour excursion offers prime photography at Helmstetter's Curve and a charming layover in Frostburg.
Rocky Gap Casino and Golf Course
8.8/10 (301 reviews)
This mountain resort blends casino gaming with outdoor adventure in Maryland's Appalachian landscape. Unwind at the lakeside spa after a round on the Jack Nicklaus Signature Golf Course.
Allegany County Fairgrounds
8.2/10 (29 reviews)
The Allegany County Fairgrounds hosts Maryland's vibrant week-long fair with national acts and agricultural exhibits. Visit in mid-July to experience demolition derbies, amusement rides, and local fair food traditions.
Lake Habeeb Beaches
8.2/10 (10 reviews)
Lake Habeeb dazzles with crystal-clear blue waters against a dramatic mountain backdrop. Three sandy beaches offer pristine swimming conditions and forested surroundings, creating a perfect natural retreat.
La Vale Tollgate House
8.2/10 (37 reviews)
This rare seven-sided toll house from 1836 stands as the last remaining on Maryland's National Road. Explore its historic architecture and interpretive displays chronicling America's westward expansion.
Canal Place
8.4/10 (56 reviews)
This historic 58-acre park marks the western end of the C&O Canal. Explore the replica boat, stroll the towpath, or catch the scenic railroad for a glimpse into America's industrial past.
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?
- 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.
- 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.
- 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.
- 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.
