Cumberland Trips (flight + hotel)

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Things to do in and around Cumberland

Shopping

The Downtown Cumberland Historic District offers a delightful shopping experience with a mix of boutiques and local shops, perfect for gifts and souvenirs. If you're up for a drive, visit Country Club Mall, where you'll find more diverse shopping options in a family-friendly atmosphere.

Recreation

Experience the vibrant atmosphere at Windsor Hall, where dance and culture intertwine for an enchanting evening. For a delightful family outing, the Palace Theater offers captivating performances just 14.5km away. Alternatively, enjoy a round of golf amidst nature at Maplehurst Country Club, located 12.9km from Cumberland.

Adventure

Explore the thrills of Mountain Ridge ATV Park, located 40.2km from Cumberland, where you can navigate rugged terrains on powerful ATVs. For a scenic hike, the Allegheny Passage, 17.7km away, offers beautiful landscapes and adventure vibes, perfect for nature enthusiasts.

Experience the adrenaline rush at Bedford Speedway, 46.7km from Cumberland, where you can witness exciting motor racing events in a vibrant sports atmosphere. It's an exhilarating way to enjoy the local culture and excitement.

Nightlife

Cumberland offers a charming nightlife with a variety of venues. Enjoy live music at the historic Palace Theatre, or unwind at the trendy 1812 Brewery for local brews. For a lively atmosphere, visit the downtown pubs where you can mingle with friendly locals and savour delicious food.

*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 idyllic destination for outdoor enthusiasts and couples seeking a romantic getaway. The area boasts a rich tapestry of attractions, including historic railways and picturesque lakes, perfect for those craving cultural and scenic experiences. Visitors can explore Lake Cumberland, revel in the breathtaking views at Cumberland Falls, and discover the beauty of Cumberland Island National Seashore, making it an excellent choice for a memorable vacation.

  • Western Maryland Scenic Railroad: Experience a journey through time aboard this historic train, offering scenic views of the Appalachian Mountains and rich local culture. The vintage carriages and knowledgeable conductors narrate tales of the region's history, making it a unique adventure for all ages.
  • Allegany County Fairgrounds: This vibrant venue hosts a variety of events throughout the year, from fairs to exhibitions, showcasing local talent and produce. The lively atmosphere and community spirit provide an engaging experience, perfect for immersing yourself in local culture.
  • C&O Canal National Historic Park Visitor's Center: Ideal for families and outdoor enthusiasts, this visitor centre offers access to stunning trails along the historic canal. You can explore nature, engage in recreational activities, and discover the area's rich 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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January29.7°F (-1.3°C)Light RainMostly CloudySlightly LowSlightly Low
February32.7°F (0.4°C)Light RainMostly CloudySlightly LowAverage
March40.6°F (4.8°C)Light RainMostly SunnySlightly LowSlightly Low
April51.1°F (10.6°C)Light RainMostly SunnyAverageAverage
May61.0°F (16.1°C)Light RainMostly SunnyAverageAverage
June69.1°F (20.6°C)Light RainMostly SunnyAverageAverage
July74.1°F (23.4°C)Light RainMostly SunnySlightly HighSlightly High
August71.8°F (22.1°C)Light RainMostly SunnySlightly HighSlightly High
September64.9°F (18.3°C)Light RainMostly SunnyAverageAverage
October53.8°F (12.1°C)Light RainMostly SunnySlightly HighSlightly High
November41.7°F (5.4°C)Light RainMostly SunnyAverageSlightly Low
December35.1°F (1.7°C)Light RainMostly CloudyAverageAverage

Tips to save on your trip to Cumberland

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Cumberland.
  • 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.

Top hotels in Cumberland

Rocky Gap Casino & Resort

Rocky Gap Casino & Resort

4 out of 5
16701 Lakeview Road NE Cumberland MD
Fully refundableReserve now, pay when you stay
The price is P6,805 per night from Nov 23 to Nov 24
P6,805
P10,007 total
Nov 23 - Nov 24
includes taxes & fees
9/10 Wonderful! (1,724 reviews)
"Make sure you make a reservation to eat in the restaurant even if they tell you you don’t need one"

Reviewed on Nov 4, 2026

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 P4,520 per night from Nov 11 to Nov 12
P4,520
P5,152 total
Nov 11 - Nov 12
includes taxes & fees
Ramada by Wyndham Cumberland Downtown
Best Western Braddock Inn

Best Western Braddock Inn

2.5 out of 5
1268 National Hwy Cumberland MD
Fully refundableReserve now, pay when you stay
The price is P4,857 per night from Nov 10 to Nov 11
P4,857
P5,536 total
Nov 10 - Nov 11
includes taxes & fees
Best Western Braddock Inn
See all 2,360 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.

Stay near popular Cumberland attractions

A train numbered 501 on tracks under a bridge.
Photo by Sig
Open 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.
See properties

What to do in Cumberland

4-Day Tour of Cumberland

4-Day Tour of Cumberland

P81,640
per adult
4-Day Tour of Cumberland
See all activities in Cumberland

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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.