A river flowing through a town with a bridge and a large building with a sign.

Cumberland Vacations from $742

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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.
  • Dec 31 - Jan 4

    Holiday Inn Express & Suites Clear Spring by IHG + Flight

    Clear Spring
    4 nights
    2.5 star property
    8.6/10 - Excellent (1,002 reviews)
    Roundtrip • Los Angeles (LAX) - Hagerstown (HGR)
    LAX - PHL • Nonstop PHL - LAX • 1 stop
    $752
    $742
    per traveler
    found 1 hour ago
    Holiday Inn Express & Suites Clear Spring by IHG
  • Dec 29 - Jan 1

    Red Roof Inn Hagerstown - Williamsport, MD + Flight

    Williamsport
    3 nights
    2.0 star property
    7.2/10 - Good (1,000 reviews)
    "Nice little town to visit. Staff friendly and helpful"
    Reviewed November 1, 2026
    Roundtrip • Los Angeles (LAX) - Hagerstown (HGR)
    LAX - PHL • Nonstop PHL - LAX • Nonstop
    $817
    $800
    per traveler
    found 1 day ago
    Red Roof Inn Hagerstown - Williamsport, MD

Where to stay in and around Cumberland

Explore the charm of downtown Cumberland, Maryland, nestled in scenic river valleys and surrounded by the majestic Maryland mountains. Ideal for outdoor enthusiasts and business travelers alike, this city offers a perfect blend of historical sites, romantic spots, and family-friendly adventures. Enjoy your stay!

Frostburg

Discover Frostburg, a charming destination perfectly suited for family travelers seeking budget-friendly adventures amidst stunning nature. Here, you can explore the scenic beauty of the Savage River and visit the historic Frostburg State University, all while enjoying recreational activities. Just about 9 miles by car from Cumberland, Frostburg offers a seamless travel experience, making it an ideal choice for your stay. Whether you're here for outdoor fun or a romantic getaway, Frostburg is a smart hotel booking choice.

LaVale

Experience the charm of LaVale, an excellent hub for outdoor enthusiasts and families eager to explore the scenic beauty of Cumberland, Maryland. This welcoming village offers easy access to attractions like the historic Western Maryland Scenic Railroad and the picturesque Allegany County Fairgrounds, perfect for creating lasting memories. With its proximity to a stunning lake and a national state park, LaVale is ideal for those seeking adventure year-round. Choosing LaVale as your base ensures a delightful stay in a vibrant community.

Cresaptown-Bel Air

If you are a family traveler or an outdoor enthusiast, look no further than Cresaptown-Bel Air, a charming village in Cumberland, Maryland. This area offers a delightful blend of scenic beauty and adventure, with attractions like the picturesque Allegany County Fairgrounds and the historic Western Maryland Scenic Railroad. Enjoy recreational activities in nearby parks and hit the greens at local golf courses. With easy access to Cumberland's attractions, Cresaptown-Bel Air is a smart choice for your stay.

Ridgeley

Ridgeley, West Virginia, stands out as a prime spot for families and budget-conscious travelers interested in outdoor adventures and scenic experiences. Just a short drive from Cumberland, Ridgeley offers access to attractions like the Western Maryland Scenic Railroad and the beautiful landscapes of the nearby national state park. With amenities that cater to everyone, this charming city is an excellent choice for a memorable stay, providing a perfect blend of relaxation and recreation.

Pinto

Travelers visiting Cumberland, Maryland, will find Pinto to be an ideal base for their vacation, featuring a family-friendly atmosphere that suits budget-conscious visitors and nature enthusiasts alike. This charming village offers access to attractions such as the urban park, the historic Western Maryland Scenic Railroad, and the Allegany County Fairgrounds, making it perfect for those seeking outdoor adventures and city-related experiences. Conveniently located within Cumberland, Pinto is a smart choice for your stay, ensuring you enjoy a delightful blend of activities and relaxation.

Discover the most popular places to visit in Cumberland

Cumberland Hotel Deals

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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.

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.

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.

Frequently Asked Questions

What's included in a Cumberland vacation package?

A Cumberland vacation package lets you combine round-trip flights, hotel stays, and a rental car, which is often useful for exploring this outdoor and nature destination. Nearly a third of package hotels offer mountain views, allowing you to fully appreciate the scenic surroundings. Additionally, some hotels here offer free breakfast, providing a convenient start to your day.


Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.

How can I save money on a Cumberland vacation package?

When you bundle, you can save up to 30%*. To save money on a Cumberland package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

What's the best vacation package for Cumberland?

For couples seeking a romantic Cumberland vacation package, The Wills Hotel, rated 9.2 out of 10, is an excellent choice. Located about a 5-minute walk from central Cumberland, it offers a bar/lounge and restaurant, perfect for evening relaxation.


Families will find a great stay at Hampton Inn Cumberland, rated 9.3 out of 10. This hotel, about 1 mile from central Cumberland, features family rooms, an indoor pool, and a game room, with travelers frequently praising the lovely pool and welcoming staff.


If you're looking for the best value among vacation packages in Cumberland, consider Comfort Inn & Suites LaVale - Cumberland. Rated 9.1 out of 10 and costing around $180 per night, it includes free breakfast, an indoor pool, and family rooms, with travelers often highlighting its great location and comfortable overall experience.


*Package availability and prices may change depending on dates and demand.

Which Cumberland vacation packages include a mountain view?

Nearly a third of Cumberland vacation packages include hotels that offer mountain views. When building your Cumberland vacation package, you can find options like The Wills Hotel, rated 9.2 out of 10 by travelers, which provides rooms with scenic outlooks. Another choice is Fairfield Inn & Suites by Marriott Cumberland, rated 8.5 out of 10, where travelers frequently praise the amazing views from their rooms. Keep in mind that specific mountain views depend on the room type and rate booked.

What are the top things to do in Cumberland?

A Cumberland vacation can focus on outdoor adventures and exploring the region's rich history:


Browse and book things to do in Cumberland on Expedia.

Do you need to rent a car in Cumberland, or is public transport enough?

For a Cumberland vacation package, a rental car is highly recommended for exploring the wider region. While the downtown area is very walkable, with a pedestrian-only mall and easy access to attractions like the Canal Place Heritage Area and the Western Maryland Scenic Railroad, a car offers the flexibility to venture further.


Allegany County Transit provides local bus service in and around Cumberland, but to truly experience the outdoor and nature attractions outside the city, such as Rocky Gap State Park or Lake Habeeb, having your own vehicle is advised. This allows you to set your own pace and reach destinations that may not be easily accessible by public transport, enhancing your Cumberland vacation packages with flights.

Are Cumberland vacation package hotels conveniently located?

Cumberland vacation package hotels offer a mix of central and slightly outlying locations, providing options for different travel styles. Many properties are within easy reach of central Cumberland, which is ideal for exploring the downtown area on foot.


For example, The Wills Hotel, rated 9.2 out of 10, is about a 5-minute walk from central Cumberland. Fairfield Inn & Suites by Marriott Cumberland, rated 8.5 out of 10, is also conveniently located about a 10-minute walk away. If you prefer a slightly quieter spot but still close to the action, Hampton Inn Cumberland, rated 9.3 out of 10, is about 1 mile from central Cumberland. These locations make it easy to access local attractions and dining during your stay.

Can I change or cancel my Cumberland vacation package if my plans change?

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Do One Key members get extra savings when booking Cumberland vacation packages?

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Does Expedia offer Book Now, Pay Later Cumberland vacation packages?

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Cumberland vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

How do I find last-minute vacation packages to Cumberland?

To find last-minute vacation packages to Cumberland, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

How does free cancellation work on Cumberland vacation packages?

Free cancellation on a Cumberland vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Is it cheaper to book a Cumberland vacation as a package or separately?

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Cumberland getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Why should I book my Cumberland vacation package with Expedia?

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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