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Cumberland vacation rentals

We found 37 vacation rentals — enter your dates for availability

Discover a selection of 8 homes and other vacation rentals in Cumberland that are perfect for your trip. Whether you're staying in a vacation rental with a group or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include parking and a garden. You'll be sure to find a rental to meet everyone's needs, including places that are non-smoking or accessible.

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Find out more about Cumberland

Why visit Cumberland

  • Scenic Outdoor Activities: Experience breathtaking landscapes perfect for hiking, biking, and nature walks.
  • Rich Historical Attractions: Discover Cumberland's heritage through its historic railways and local museums.
  • Family-Friendly Experiences: Enjoy a variety of attractions suitable for travelers of all ages.
  • Romantic Getaways: Take peaceful strolls around serene lakes, ideal for couples.
  • Diverse Accommodation Options: Choose from cozy cabins, private homes, and charming cottages for your stay.

Popular types of accommodation in Cumberland

When it comes to vacation rentals in Cumberland, Vrbo has you covered with a variety of options. Whether you're looking for cozy cabins, houses, or charming holiday cottages, there's something for everyone. Our travelers often choose from house rentals, Cumberland motels, or delightful cottages, depending on their needs and plans. Explore the perfect escape that suits your style and enjoy a memorable getaway in beautiful Cumberland.

  • Cabins: The top choice for vacation rentals in Cumberland, offering a cozy and rustic atmosphere amidst nature.
  • Houses: Ideal for families or groups, these homes provide spacious accommodations and a home-like feel.
  • Cottages: Charming and quaint, these smaller homes are perfect for a romantic getaway or peaceful retreat.
  • Chalets: These stylish mountain-style lodgings offer a unique experience with scenic views.
  • Apartments: Convenient and comfortable, apartments are perfect for those seeking a central location with essential amenities.**

Top attractions in Cumberland

Cumberland, Maryland, is perfect for outdoor and romantic vacations, offering stunning scenery and a rich history. Visitors can explore local attractions such as serene lakes, historic railways, and golf course resorts. Whether you're seeking cultural experiences or outdoor adventures, Cumberland has something for everyone, making it an ideal destination for solo travelers, couples, or families looking to enjoy a memorable getaway.

  • Western Maryland Scenic Railroad: Experience a journey through picturesque landscapes on this historic train. The scenic route offers a glimpse into the region's rich cultural history and stunning views of the surrounding mountains.
  • Lake Habeeb Beaches: Enjoy a relaxing day at the beautiful beaches of Lake Habeeb. With its serene waters, stunning scenery, and perfect spots for romance, it's an ideal destination for outdoor activities and picnics.
  • Rocky Gap Golf Resort: Play a round of golf at this picturesque resort, featuring breathtaking views and a friendly atmosphere. Explore the historical significance of the area while enjoying various outdoor excursions.

Things to do recommended for couples

Planning a romantic getaway in Cumberland? Be sure to experience the lively atmosphere of Windsor Hall, where you can dance the night away surrounded by culture and entertainment. It's the perfect spot to create unforgettable memories together.

Things to do recommended for families

Families visiting Cumberland can explore the stunning trails at the Great Allegheny Passage, enjoy a ride on the Western Maryland Scenic Railroad, and discover history at the C&O Canal National Historical Park, offering engaging activities for all ages.

Things to do recommended for groups

In Cumberland, groups can enjoy shopping and entertainment in the Downtown Historic District, catch a show at the Palace Theater for a dose of culture, or unwind with a round of golf at Maplehurst Country Club, embracing the outdoor vibe just a short drive away.

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

What do I need to keep in mind when booking a vacation in Cumberland

If you're traveling with a group, with family, bringing along pets, or planning an extended stay, be sure to use filters that align with your specific needs. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Cumberland with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor area for group gatherings. Luckily, you can easily refine your search for all of these options, and much more, on Vrbo.
  • Traveling to Cumberland with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with amenities suited for their age, like a private swimming pool. Additionally, you might want to think about how close you are to attractions that are family-friendly.
  • Taking your pets with you to Cumberland: For many, a family vacation isn't truly whole without their furry companion by their side. If you can relate, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Cumberland: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Cumberland

Cumberland, Maryland, is a charming destination perfect for outdoor enthusiasts and those seeking a relaxing getaway. Nestled in the heart of Western Maryland, this city offers a blend of scenic beauty and rich history. Explore family-friendly attractions, enjoy romantic strolls, and immerse yourself in the area's friendly atmosphere. Whether you're looking for a perfect family vacation or a tranquil escape, Cumberland and its surrounding neighborhoods have something special to offer every traveler.

  • Frostburg: Situated 9 miles from Cumberland, Frostburg is a charming city known for its stunning outdoor scenery and romantic atmosphere. This destination is perfect for nature enthusiasts and those seeking a peaceful retreat. Visitors can explore the nearby national state park, offering a myriad of hiking trails and picturesque landscapes. Frostburg State University adds an educational flair to the city, while the local lake provides excellent recreational opportunities such as fishing and boating. Whether you’re enjoying a scenic walk or a cozy evening in a café, Frostburg offers an inviting escape.
  • LaVale: Nestled within the Cumberland area, LaVale is a quaint village that attracts travelers with its beautiful outdoor settings and scenic views. This charming locale is home to various recreational areas, perfect for a day of hiking or picnicking. LaVale also boasts an entertainment arena, making it a great spot for catching local events. The nearby lake and historic sites enrich the experience, allowing visitors to soak in the area’s culture and history. LaVale’s intimate atmosphere makes it an ideal destination for couples seeking a romantic getaway.
  • Ridgeley: Just 1 mile from Cumberland, Ridgeley is a delightful city that combines outdoor adventure with scenic beauty. This area is perfect for those looking to engage in recreational activities, with easy access to parks and educational venues. Ridgeley’s proximity to a beautiful lake and national state park offers ample opportunities for hiking, fishing, and exploring nature. The historic places within the city add a layer of charm and intrigue, making it a fascinating stop for history buffs and outdoor lovers alike.

Best time to go to Cumberland

If you're planning a trip to Cumberland, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like January to March tend to have fewer bookings and better deals.

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

Booking with Vrbo is simple

Are you eager to save on your upcoming journey? Being flexible with your travel dates can really help, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, feel free to utilize our filters to sort by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve an eligible Vrbo for your group getaway and earn OneKeyCash on your booking. Being the organizer has its perks. When you join our travel rewards program, One Key, you'll gain immediate access to member discounts and the opportunity to earn and redeem OneKeyCash on qualifying reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a convenient platform to plan new trips, pick up right where you left off, and manage your travel arrangements effortlessly. You can easily access properties you've saved or booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

The majestic setting of Cumberland is ready to explore

The area's history and churches are just a few of the reasons to vacation in Cumberland. Travelers to this scenic city praise the casino gaming, hiking and biking. Whether you're planning a family vacation, friends trip or romantic retreat, Vrbo has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in and around Cumberland

Do you want to find attractions to visit while you're in the area? You'll be sure to enjoy Cumberland for its hiking and biking. Venture out of your cozy vacation rental and experience everything that Cumberland has to offer. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Allegany County Fairgrounds (3.6 mi / 5.9 km)
  • Rocky Gap Casino and Golf Course (6.5 mi / 10.4 km)
  • Tri-State Zoological Park (2.5 mi / 4.1 km)

Exploring the natural features in Cumberland

Travelers enjoy Cumberland for its mountain views, riverfront and lakeside setting. Whether you're an adventurous traveler or just want to appreciate the scenery, Cumberland is a great place to get outside. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Lake Habeeb Beaches (6.8 mi / 10.9 km)
  • Allegheny Passage (10.7 mi / 17.2 km)
  • Savage River (11 mi / 17.7 km)
  • Canal Place (0.3 mi / 0.6 km)
  • Lake Habeeb (6.9 mi / 11.1 km)
  • Green Ridge State Forest (17 mi / 27.4 km)

How to get to and around Cumberland

The nearest airport is in Hagerstown, MD (HGR-Hagerstown Regional), located 54.9 mi (88.4 km) from the city center.

If you prefer train travel, make your way to Cumberland Station or Allegany College Bus Stop to see more of the city.

Frequently asked questions

What is the best area to stay in Cumberland, Maryland, United States of America when booking a vacation rental?
When considering a vacation rental in Cumberland, Maryland, you'll find that the downtown area is an excellent choice. This vibrant neighborhood offers a mix of historic charm and modern amenities, making it a delightful place to explore. You'll be close to attractions like the Allegany Museum, which showcases the rich history and culture of the region, and the scenic Great Allegheny Passage, superb for outdoor enthusiasts looking to hike or bike along its picturesque trails.

Another great option is the area around the Cumberland City Park, which provides a more relaxed atmosphere while still being conveniently located. Here, you can enjoy the beautiful green spaces, as well as nearby attractions like the historic Western Maryland Scenic Railroad, where you can take a scenic train ride through the stunning landscapes of western Maryland.

Overall, both neighborhoods offer a variety of properties, ranging from charming historic homes to modern rentals, ensuring you'll find something that suits your needs.
How much does it cost to rent a vacation home in Cumberland?
Prices for vacation rentals in Cumberland vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Cumberland to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Cumberland vacation house rentals?
You can find great discounts on house rentals in Cumberland on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best Cumberland ski resort rentals?
For ski resort rentals near Cumberland, travelers should consider the nearby Wisp Resort, located about an hour's drive from Cumberland in McHenry, Maryland. This area offers a variety of lodging options, including cozy cabins and chalets that often feature amenities like fireplaces, full kitchens, and outdoor decks for enjoying the scenic mountain views. Many properties here cater to families and groups, providing ample space and comfortable living areas for relaxation after a day on the slopes.

In the vicinity of Wisp Resort, the Deep Creek Lake area is particularly appealing, with vacation rentals that provide easy access to both skiing and the beautiful lake. Many of these rentals come with amenities such as hot tubs, game rooms, and proximity to hiking trails and winter sports activities, making them ideal for those looking to enjoy a winter getaway. The charming local shops and restaurants in McHenry and surrounding areas add convenience for travelers, ensuring a delightful experience both on and off the mountain.
What is the most popular type of vacation rental accomodation in Cumberland?
In Cumberland, a variety of vacation rentals can be found, including vacation houses, apartments, cottages, cabins, and campsites, each offering a great experience. Many of these properties are situated in scenic areas that provide easy access to local attractions such as the historic downtown, the Great Allegheny Passage, and the beautiful Western Maryland Scenic Railroad.

Travelers can expect vacation houses to feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups. Apartments typically provide a more compact, convenient option with modern amenities, while cottages and cabins often bring a rustic charm with cozy interiors and outdoor spaces for relaxation. Campsites cater to those looking for a more adventurous stay, offering a connection to nature.
Are there any family house rentals in Cumberland?
In Cumberland, Maryland, there are some family-friendly house rentals available, with around 15 options to choose from. This charming city offers a mix of historic and modern neighborhoods, providing ample opportunities for families to enjoy their stay. Many of these homes feature spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces where children can play or families can gather for barbecues.

Visitors will appreciate the proximity to local attractions such as the C&O Canal National Historical Park, which offers beautiful trails for hiking and biking, as well as the scenic Great Allegheny Passage for outdoor adventures. Additionally, families can explore downtown Cumberland, where they'll find shops, restaurants, and cultural sites that showcase the area's rich history.
Can I rent a vacation home with a pool or hot tub in Cumberland?
In Cumberland, Maryland, there are several vacation homes available for rent that feature pools and hot tubs. This charming city, located in the Appalachian Mountains, offers a variety of accommodations suited for travelers looking to relax and unwind. Many properties come with amenities such as private pools, outdoor hot tubs, and spacious patios, making them great for family gatherings or group retreats. Additionally, travelers can expect fully equipped kitchens, comfortable living areas, and sometimes even game rooms, enhancing the overall experience. Find your rental in Cumberland with a pool or a hot tub.
Can I find long-stay vacation rentals in Cumberland?
A long-stay vacation rental in Cumberland is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Cumberland?
In Cumberland, Maryland, there are several pet-friendly house rentals available for travelers seeking a comfortable stay. Many of these properties are equipped with essential amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces, ideal for families or groups traveling with pets. The city is surrounded by beautiful natural landscapes, providing opportunities for outdoor activities with your furry companions.

Nearby, the scenic Great Allegheny Passage offers numerous walking and biking trails, great for pet owners who enjoy exploring the outdoors. Additionally, the area features various parks where pets are welcome, enhancing the overall experience for travelers with pets.
Are there any remote work vacation rentals in Cumberland?
In Cumberland, Maryland, there are about 16 vacation rentals that are well-suited for remote work, making it a convenient choice for those looking to blend work and leisure. Many of these properties offer amenities such as free Wi-Fi, dedicated workspaces, and comfortable living areas, allowing for an efficient work-from-home experience.

Travelers can expect a variety of accommodations, including cozy apartments and charming houses, which often come equipped with full kitchens for meal preparation and laundry facilities for added convenience. The scenic surroundings of Cumberland, with its rich history and access to outdoor activities, provide a great backdrop for unwinding after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Cumberland vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Cumberland with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Cumberland?
In Cumberland, popular vacation rental amenities include kitchens, which allow travelers to prepare their own meals and enjoy a home-like experience. Many rentals also feature decks or patios, providing outdoor spaces to relax and take in the scenic views of the surrounding area. Additionally, coffee and tea makers are commonly found in these properties, ensuring guests can start their day with a warm beverage. Onsite parking is another convenient amenity, making it easier for guests to explore the local attractions. Many rentals also offer porches or lanais, superb for enjoying the fresh air and local charm.
When is the best time to visit Cumberland for a vacation rental?
September is the most popular time to visit Cumberland, Maryland, as it marks the transition into the beautiful fall season. This month attracts travelers keen on enjoying outdoor activities such as hiking and biking, all while basking in the mild temperatures, typically ranging from the low 50s to mid-70s Fahrenheit. The surrounding Appalachian Mountains provide a stunning backdrop, making it an ideal time for sightseeing and leisurely strolls.

The peak travel season in Cumberland spans from August to October, with August being particularly vibrant. During this time, you'll find a mix of outdoor enthusiasts and families taking advantage of summer's last hurrah before the cooler weather sets in. The region is alive with events and activities, offering a wealth of options for both adventure and relaxation.

If you are looking for a more budget-friendly option, consider planning your trip in May. This month offers a quieter experience while still allowing you to appreciate the lush greenery and blooming flowers as spring unfolds. Enjoy the peace of the area and explore local attractions without the hustle and bustle of the peak season.

Ultimately, the best time to book a vacation rental in Cumberland hinges on your preference for lively summer activities or the serene beauty of early fall.
How early should I book a Cumberland vacation rental?
Book your Cumberland vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Cumberland, Maryland, United States of America?
In Cumberland, Maryland, visitors can explore a variety of attractions that highlight the area's rich history and natural beauty. The downtown area features the historic Western Maryland Scenic Railroad, where travelers can enjoy scenic train rides along the picturesque mountains and valleys. Nearby, the Allegany Museum offers insights into the local heritage, showcasing artifacts and exhibits related to the region's railroad and mining history.

For outdoor enthusiasts, the Great Allegheny Passage provides miles of trails for hiking and biking, connecting Cumberland to Pittsburgh. The scenic vistas along the trail make it a popular spot for nature lovers. Additionally, the nearby Rocky Gap State Park offers recreational opportunities such as fishing, hiking, and golfing, with stunning views of the lake and surrounding mountains.

Cumberland's location also provides easy access to the scenic Potomac River, where visitors can partake in kayaking and canoeing.
Can I change or cancel my Cumberland home rental booking on Vrbo?
To find Cumberland vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Cumberland vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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