How much does a Cumberland vacation package cost?

You'll find cheap prices from $529 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?

Pick your travel dates: What you plan to do in Cumberland and your preferred season will help you decide when to go. 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. 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. 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. Combine your accommodations and airfare: After you've nailed down your trip dates and duration, lock in the ideal Cumberland vacation package for you. 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.

Cumberland Vacation Packages 2026 from $529

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.

University Hotel & Suites Shippensburg, Trademark by Wyndham

$529

per person

May 29 - Jun 1

found 8 hours ago

Roundtrip non-stop flight included

Miami (MIA) to Hagerstown (HGR)

8.8/10 Excellent! (994 reviews)

Clean room and comfortable bed

Reviewed on Mar 1, 2026

Holiday Inn Express & Suites Shippensburg by IHG

$573

per person

May 29 - Jun 1

found 8 hours ago

Roundtrip non-stop flight included

Miami (MIA) to Hagerstown (HGR)

9.2/10 Wonderful! (764 reviews)

Yes the room was clean and the staff was very friendly. Also the breakfast buffet was amazing. I would definitely stay there again.

Reviewed on Feb 28, 2026

Mountain Dreams

$1,749

per person

May 28 - Jun 1

found 1 day ago

Roundtrip non-stop flight included

Kansas City (MKC) to Hagerstown (HGR)

No reviews

Westwind

$1,610

per person

May 28 - Jun 1

found 1 day ago

Roundtrip non-stop flight included

Kansas City (MKC) to Hagerstown (HGR)

No reviews

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Cumberland Hotel Deals

Sleep Inn & Suites Cumberland - LaVale

13320 Ali Ghan Road NE Cumberland MD

Fully refundable

$93 nightly

$106 total

Mar 25 - Mar 26

Total with taxes and fees

9.2/10 Wonderful! (1,001 reviews)

Staff was friendly. Room was nice and clean. Breakfast was decent enough

Reviewed on Feb 25, 2026

Ramada by Wyndham Cumberland Downtown

100 South George Street Cumberland MD

Fully refundableReserve now, pay when you stay

$73 nightly

$83 total

Mar 29 - Mar 30

Total with taxes and fees

6.8/10 (1,000 reviews)

Very clean, staff helpful.

Reviewed on Feb 25, 2026

Hampton Inn Cumberland

109 Welton Dr Cumberland MD

Fully refundableReserve now, pay when you stay

$108 nightly

$123 total

Mar 13 - Mar 14

Total with taxes and fees

9.6/10 Exceptional! (648 reviews)

ROOM WAS VERY CLEAN AND COMFORTABLE,GREAT BREAKFAST STAFF VERY FRIENDLT AND HELPFUL.OUR GRANDCHILDREN LOVED THE POOL CLEANEST I'VE SEEN

Reviewed on Mar 1, 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.

Things to do in and around Cumberland

Cumberland, Maryland, is perfect for outdoor and romantic getaways, offering a range of activities such as kayaking trips, picnicking in scenic areas, and enjoying local golf courses. Visitors can explore recreational areas and take part in seasonal festivities and upcoming events, making it an ideal destination for nature lovers and adventurers alike.

Shopping

For a unique shopping experience, explore the Downtown Cumberland Historic District, where you'll find local shops and boutiques reflecting the city's charm. If you're up for a drive, check out the Country Club Mall, offering a larger selection of stores and family-friendly entertainment options.

Recreation

Windsor Hall in Cumberland offers a vibrant dance experience, perfect for immersing yourself in local culture and romance. Just 8 miles away, Maplehurst Country Club invites you to enjoy outdoor sports and golfing. Meanwhile, Music at Penn Alps, 20 miles from Cumberland, presents engaging theater performances for the whole family.

Adventure

Experience the thrill of off-roading at Mountain Ridge ATV Park, located 25 miles from Cumberland. For speed enthusiasts, Bedford Speedway offers exciting motor racing 29 miles away. Additionally, enjoy the scenic beauty of the Schellsburg / Shawnee Loop, an outdoor adventure spot also 29 miles from town.

Nightlife

Cumberland's nightlife offers a charming mix of local bars and live music. Visit The Toasted Goat for unique wines and a cozy vibe, or head to the Allegany Museum for special events. For a lively atmosphere, check out the nightlife at the nearby pubs and enjoy the local talents.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Cumberland

Cumberland, Maryland, is an ideal destination for outdoor enthusiasts and couples seeking a romantic getaway. Visitors can explore attractions like Lake Cumberland, known for its breathtaking views, as well as historic rail sites and golf resorts. For a scenic experience, don’t miss Cumberland Falls and the nearby Cumberland Island National Seashore, which showcase the area’s natural beauty and cultural heritage, making it perfect for travelers looking for adventure and relaxation.

Western Maryland Scenic Railroad: Experience a nostalgic journey on this historic railroad, where you can take in the stunning landscapes of Western Maryland. The vintage trains offer a unique glimpse into the region's rich cultural heritage, making it a delightful adventure for history buffs and families alike.
Lake Habeeb Beaches: Relax at the beautiful Lake Habeeb Beaches, where you can enjoy sun-soaked days by the water. The scenic surroundings provide a perfect backdrop for outdoor activities, romantic picnics, or simply soaking up the natural beauty of the area.
C&O Canal National Historic Park Visitor's Center: Embark on an adventurous day at the C&O Canal National Historic Park Visitor's Center. Ideal for families, this site offers engaging exhibits and access to numerous outdoor trails, perfect for hiking and exploring the canal's history.

Best time to go to Cumberland

The best time to visit Cumberland is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly cloudy with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	29.7°F (-1.3°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly Low
February	32.7°F (0.4°C)	Light Rain	Mostly Cloudy	Slightly Low	Average
March	40.6°F (4.8°C)	Light Rain	Mostly Sunny	Average	Slightly Low
April	51.1°F (10.6°C)	Light Rain	Mostly Sunny	Average	Average
May	61.0°F (16.1°C)	Light Rain	Mostly Sunny	Average	Average
June	69.1°F (20.6°C)	Light Rain	Mostly Sunny	Slightly High	Average
July	74.1°F (23.4°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	71.8°F (22.1°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
September	64.9°F (18.3°C)	Light Rain	Mostly Sunny	Average	Average
October	53.8°F (12.1°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	41.7°F (5.4°C)	Light Rain	Mostly Sunny	Average	Slightly Low
December	35.1°F (1.7°C)	Light Rain	Mostly Cloudy	Slightly Low	Average

Tips to save on your trip to Cumberland

Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
Consider traveling to Cumberland during the low season (January, March and November) for more affordable options.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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

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