Cumberland Vacations from $338

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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.
2-Bedroom cabin Hot tub Fireplace PS5

2-Bedroom cabin Hot tub Fireplace PS5

The Woods
$338
per person
Dec 11 - Dec 14
found 6 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Hagerstown (HGR)
6.4/10 (12 reviews)
This cabin needs a LOT of care. It was OK for our purposes, because we just needed a place to sleep more than anything, but if we were actually looking to "vacation" or "rest and relax" it left a lot to be desired--especially regarding upkeep and how it was furnished 1. Our sheets had HOLES in them! 2. No toiletries, other than body wash in the bathroom 3. No bath mat 4. Insufficient towels 5. Not enough dishes or mugs 6. No sponge for washing dishes, or anything to clean and wipe down counters 7. Furniture had stains, basically didn't look very clean 8. Vertical blinds were missing many, many verticals. No privacy in living areas.

Reviewed on Sep 9, 2026

Highland Retreat by Taylor Made Deep Creek

Save 100% on your flight
$1,079
per person
Dec 11 - Dec 14
found 6 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Hagerstown (HGR)
No reviews

Wander Inn by Taylor Made Deep Creek

$784
per person
Dec 11 - Dec 14
found 6 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Hagerstown (HGR)
No reviews
Canadian Day by Taylor Made Deep Creek

Canadian Day by Taylor Made Deep Creek

$792
per person
Dec 11 - Dec 14
found 6 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Hagerstown (HGR)
No reviews
Green Gables by Taylor Made Deep Creek

Green Gables by Taylor Made Deep Creek

$661
per person
Dec 11 - Dec 14
found 6 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Hagerstown (HGR)
No reviews
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Stay near popular Cumberland attractions

A train numbered 501 on tracks under a bridge.
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.
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A calm lake with a person paddleboarding, surrounded by autumn-colored trees.

Lake Habeeb

9.0/10 (8 reviews)
Lake Habeeb's crystal-clear waters create a stunning blue centerpiece within Rocky Gap State Park. Enjoy premium fishing for bass and trout or hike the scenic Lakeside Loop for breathtaking mountain reflections.
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Western Maryland Scenic Railroad

9.0/10 (224 reviews)
Journey through the Allegheny Mountains on a historic steam locomotive while admiring picturesque landscapes. The 4-hour excursion offers prime photography at Helmstetter's Curve and a charming layover in Frostburg.
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Rocky Gap Casino and Golf Course

8.8/10 (301 reviews)
This mountain resort blends casino gaming with outdoor adventure in Maryland's Appalachian landscape. Unwind at the lakeside spa after a round on the Jack Nicklaus Signature Golf Course.
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Allegany County Fairgrounds

8.2/10 (29 reviews)
The Allegany County Fairgrounds hosts Maryland's vibrant week-long fair with national acts and agricultural exhibits. Visit in mid-July to experience demolition derbies, amusement rides, and local fair food traditions.
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Lake Habeeb Beaches

8.2/10 (10 reviews)
Lake Habeeb dazzles with crystal-clear blue waters against a dramatic mountain backdrop. Three sandy beaches offer pristine swimming conditions and forested surroundings, creating a perfect natural retreat.
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Canal Place

8.4/10 (56 reviews)
This historic 58-acre park marks the western end of the C&O Canal. Explore the replica boat, stroll the towpath, or catch the scenic railroad for a glimpse into America's industrial past.
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Country Club Mall

8.0/10 (97 reviews)
This regional shopping hub offers retail therapy, dining options, and an AMC theater under one roof. Visit during holiday seasons to experience festive decorations and special community events.
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Cumberland Hotel Deals

Rocky Gap Casino & Resort

Rocky Gap Casino & Resort

16701 Lakeview Road NE Cumberland MD
$140 nightly
$160 total
Nov 2 - Nov 3
Total with taxes and fees
9/10 Wonderful! (1,704 reviews)
"Very easy check in and was quick. Casino was not packed and was so relieved they have designated smoking. Would go again."

Reviewed on Oct 13, 2026

Rocky Gap Casino & Resort
Ramada by Wyndham Cumberland Downtown

Ramada by Wyndham Cumberland Downtown

100 South George Street Cumberland MD
Fully refundableReserve now, pay when you stay
$70 nightly
$80 total
Nov 8 - Nov 9
Total with taxes and fees
6.8/10 (1,006 reviews)
"Property provided a place to sleep but not much more. There is notbactual worker working the front desk, just a guy on a tablet talking to you from a screen from remote location. They have no type of helpfulness for guests. I had a party with six rooms and we asked if we could have early check in ..."

Reviewed on Oct 11, 2026

Ramada by Wyndham Cumberland Downtown
Sleep Inn & Suites Cumberland - LaVale

Sleep Inn & Suites Cumberland - LaVale

13320 Ali Ghan Road NE Cumberland MD
Fully refundable
$80 nightly
$91 total
Nov 8 - Nov 9
Total with taxes and fees
9.2/10 Wonderful! (1,000 reviews)
"good"

Reviewed on Oct 13, 2026

Sleep Inn & Suites Cumberland - LaVale
See all 2,354 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

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.

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 SunnyAverageSlightly 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 SunnySlightly HighAverage
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 SunnyAverageSlightly High
November41.7°F (5.4°C)Light RainMostly SunnyAverageSlightly Low
December35.1°F (1.7°C)Light RainMostly CloudySlightly LowAverage

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.

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

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.

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