Cumberland Vacations from $674

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Your Cumberland Vacation

You'll find plenty to like about Cumberland, from its laid-back lifestyle to its family-friendly attractions. When you're ready to say hello to this interesting city, our Cumberland vacation packages will be just the thing. If sightseeing is on the to-do list during your trip to Cumberland, visit big attractions like Western Maryland Railroad Station, Downtown Cumberland Historic District and Canal Place. Expedia has what you need to escape the everyday. Tailor your vacation to Cumberland to match your travel style, whatever that may look like.

The Latest Cumberland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Rocky Gap Casino & Resort

Rocky Gap Casino & Resort

3 out of 5
Save 100% on your flight
per person
Jul 9 - Jul 14
found 8 hours ago
Roundtrip flight included
Dallas (DFW) to Hagerstown (HGR)
8.8/10 Excellent! (1,001 reviews)
Very nice midweek stay.

Reviewed on May 30, 2024

Big and Boulder

Big and Boulder

4 out of 5
Save 100% on your flight
per person
Jul 9 - Jul 14
found 8 hours ago
Roundtrip flight included
Dallas (DFW) to Hagerstown (HGR)
No reviews

Cumberland Essential Information

Language
English
Currency
U.S dollars
Population
20,100
Max Temp Winter
40ºF
Max Temp Summer
85ºF
Top Sights
Rocky Gap State Park, Dans Mountain State Park and Tri-State Zoological Park

Cumberland Hotel Deals

Rocky Gap Casino & Resort
Rocky Gap Casino & Resort
3 out of 5
16701 Lakeview Road NE, Cumberland, MD
The price is $129 per night from Jun 3 to Jun 4
$129
$177 total
includes taxes & fees
Jun 3 - Jun 4
8.6/10 Excellent! (1,003 reviews)
Amazing Stay
"Amazing stay. Wonderful customer service. Clean and comfortable rooms. Great return in the casino. Beautiful outdoor scenery. Especially the new added beach area. If this resort adds more late night dining options and more entertainment this’ll be the best hidden gem in the state of Maryland."

Reviewed on May 29, 2024

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 $88 per night from Jun 17 to Jun 18
$88
$101 total
includes taxes & fees
Jun 17 - Jun 18
7/10 Good! (1,002 reviews)
"Great location! Near churches, train station, & Fairgrounds."

Reviewed on May 30, 2024

Ramada by Wyndham Cumberland Downtown
Secluded, romantic cabin with hot tub on 12 acres of woodland.
Secluded, romantic cabin with hot tub on 12 acres of woodland.
Cumberland
The price is $195 per night from Jun 5 to Jun 6
$195
$329 total
includes taxes & fees
Jun 5 - Jun 6
10/10 Exceptional! (55 reviews)
Beautiful Little Cottage
"We greatly enjoyed r stay at this little cottage & would definitely recommend! My husband & I both love the outdoors & took the opportunity to do some hiking at Rocky Gap State Park close by, which had some great trails & beautiful scenery!"

Reviewed on May 4, 2024

Secluded, romantic cabin with hot tub on 12 acres of woodland.
See all 2,657 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

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Cumberland vacation package cost?
Our Cumberland vacation packages, which begin from just $674, are an awesome way to save precious money. Handpick your favorite hotels, flights and more to create a custom-built itinerary.
How do I get a cheap travel package to Cumberland?
You’ll save a pile of money if you combine your car rentals, flights and hotels into a Cumberland travel package. Sometimes cheap means fewer choices. But that’s not the case with Expedia. We offer over 550 partner airlines and 1,000,000 hotels globally, so you’ll always have plenty of variety to choose from. Like to save even more? Add some popular activities to your package deal and unlock even more discounts! After all, travel is about more than simply getting to your destination.
Where should I stay in Cumberland?
Stay where the action happens. Many people book hotels in the vicinity of top attractions, such as Rocky Gap Casino and Golf Course, Western Maryland Railroad Station and Downtown Cumberland Historic District.
What are the top hotels in Cumberland?
Best Western Braddock Inn is a sought-after Bowmans Addition hotel. Alternatively, if you intend to stay in Bel Air, consider checking in to Best Western Braddock Inn.
How far in advance should I book my Cumberland vacation?
While not all airlines advertise tickets early, you can usually start comparing international fares on Expedia up to a year in advance. This is the time when you’ll bag some incredible deals. If you’ve left everything to the last minute, there’s a chance you could get lucky. Low prices sometimes appear just weeks before departure.
What does an Expedia Cumberland travel package include?
Expedia has all you need to plan your Cumberland getaway, but what goes into your package is entirely up to you. Choose from any combination of hotels, flights and rental cars. After some activities or tours to keep you busy? Once you’ve made your booking, you can add them too. No matter your style, there’s a vacation package to suit your needs.
What should I know before booking a Cumberland travel package?
Our prices are already low. However, you’ll snap up even better deals if you book your flights, hotels and car rentals together. With an Expedia package, you’ll get transparent pricing and tons of choice.
If I'm not able to travel, can I cancel my Cumberland vacation package?
Certainly, and we’ll help you every step of the way. You may be able to amend or cancel your Cumberland vacation package for free within 24 hours of booking. However, you may incur a fee from your airline, hotel or car rental company for older bookings. If your travel plans unexpectedly change, take a look at our Customer Service Portal for further information.

Discover the most popular places to visit in Cumberland

Image for 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
Image for Rocky Gap Casino and Golf Course

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
Image for Western Maryland Railroad Station

Western Maryland Railroad Station

4.5/5(49 reviews)

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

Western Maryland Railroad Station

Other vacations you might like

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