Cumberland Vacations from $283

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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.
Super 8 by Wyndham Hancock MD

Super 8 by Wyndham Hancock MD

2 out of 5
per person
Sep 14 - Sep 17
found 24 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Hagerstown (HGR)
7/10 Good! (626 reviews)
Staff was friendly.

Reviewed on Jul 4, 2025

Liberty Mountain Resort

Liberty Mountain Resort

2.5 out of 5
per person
Sep 14 - Sep 17
found 24 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Hagerstown (HGR)
8.8/10 Excellent! (444 reviews)
Very nice place. Very clean and views were great!

Reviewed on Jun 6, 2025

2-Bedroom cabin Hot tub Fireplace PS5

2-Bedroom cabin Hot tub Fireplace PS5

2 out of 5
The Woods
per person
Sep 14 - Sep 17
found 24 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Hagerstown (HGR)
No reviews
HomeTowne Studios Hagerstown - Williamsport, MD

HomeTowne Studios Hagerstown - Williamsport, MD

3 out of 5
per person
Sep 14 - Sep 17
found 24 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Hagerstown (HGR)
7.6/10 Good! (20 reviews)
They were very accomodating

Reviewed on Jun 29, 2025

Holiday Inn Express & Suites Clear Spring by IHG

Holiday Inn Express & Suites Clear Spring by IHG

2.5 out of 5
per person
Sep 14 - Sep 17
found 24 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Hagerstown (HGR)
8.4/10 Very Good! (1,002 reviews)
Needs a good update and a deep cleaning! Staff was okay… breakfast was good.

Reviewed on Jun 29, 2025

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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
$172 nightly
The price is $196 total per night from Jul 27 to Jul 28
$196 total
Jul 27 - Jul 28
Total includes taxes and fees
8.8/10 Excellent! (1,216 reviews)
"Wonderful experience.. looking forward to our return trip next year!"

Reviewed on Jul 3, 2025

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
$86 nightly
The price is $98 total per night from Jul 14 to Jul 15
$98 total
Jul 14 - Jul 15
Total includes taxes and fees
6.8/10 (1,003 reviews)
"The over night front desk clerk was amazing"

Reviewed on Jun 22, 2025

Ramada by Wyndham Cumberland Downtown
Comfort Inn & Suites LaVale - Cumberland
Comfort Inn & Suites LaVale - Cumberland
2.5 out of 5
1216 National Hwy, Cumberland, MD
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $144 total per night from Aug 3 to Aug 4
$144 total
Aug 3 - Aug 4
Total includes taxes and fees
9.2/10 Wonderful! (1,007 reviews)
"Blackout curtains, AC, water pressure etc all worked very well making for a restful stop."

Reviewed on Jun 24, 2025

Comfort Inn & Suites LaVale - Cumberland
See all 2,640 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.

Find the Best Cumberland Vacation Packages

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

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Frequently asked questions

How much does a Cumberland vacation package cost?
You'll find cheap prices from $283 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.