Cumberland holiday lettings

We found 36 holiday rentals — enter your dates for availability

Discover a selection of 10 homes, 10 apartments and other holiday rentals in Cumberland that are perfect for your trip. Whether you're staying in a holiday rental with friends, family or even just your pets, you'll have the amenities that you expect and more, such as Wi-Fi and cable TV. You'll be able to choose a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Cumberland

Showing deals for:20 Feb - 27 Feb

Image gallery for Knit Inn..

Living area
9.4 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)

Knit Inn..

Frostburg, MD

8% off
Price is £2,759
for 7 nights, 1 home
£394 per night
includes taxes & fees
Knit Inn..

Find spaces that suit your style

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Why visit Cumberland

  • Scenic outdoor adventures: Cumberland boasts stunning natural landscapes ideal for romantic walks and family outings.
  • Rich historical charm: Explore the city's historic railways and cultural venues that showcase its heritage.
  • Welcoming neighbourhoods: Discover friendly locals and trendy spots in nearby areas that enhance the charming atmosphere.
  • Diverse accommodation options: Choose from delightful cabins, private holiday homes, and cosy cottages for your stay.
  • Picturesque lakes: Enjoy the serene beauty of Cumberland's lakes, perfect for relaxation and outdoor activities.

Popular types of accommodation in Cumberland

If you're wondering about the types of accommodation available for your stay in Cumberland, look no further. Our most sought-after options include charming cabins, private holiday homes, and delightful cottages. Whether you're searching for a spacious Cumberland house, a cosy apartment, or a relaxing retreat on Cumberland Terrace, we have a variety of holiday rentals to suit your needs. Enjoy transparency, savings, and reassurance as you plan your perfect getaway.

  • Cabins: The top choice for holidaymakers in Cumberland, offering a rustic charm amidst nature.
  • Houses: A popular option for families and groups seeking comfort and privacy during their stay.
  • Cottages: Quaint and cosy, these delightful retreats provide a homely atmosphere for visitors.
  • Chalets: Ideal for those wanting a unique blend of style and comfort, often set in picturesque locations.
  • Apartments: A convenient choice for independent travellers, providing essential amenities in central locations.**

Top attractions in Cumberland

Cumberland, Maryland, is a delightful destination for those seeking outdoor adventures and scenic beauty, perfect for romantic getaways. Visitors can explore a variety of attractions, including picturesque lakes, historic railways, and event venues that showcase the area's rich culture. Whether you're travelling solo, as a couple, or with family, Cumberland offers a charming blend of experiences to enjoy during your stay.

  • Western Maryland Scenic Railroad: Experience a nostalgic journey on this historic railway, where you can enjoy stunning views of the Appalachian Mountains and learn about the region's rich cultural heritage through engaging narratives.
  • Allegany County Fairgrounds: This vibrant venue hosts a variety of events and fairs throughout the year, showcasing local businesses and providing a lively atmosphere perfect for mingling and enjoying community spirit.
  • C&O Canal National Historic Park Visitor's Center: Offering a perfect blend of adventure and education, this centre is ideal for families looking to explore the scenic trails and learn about the history of the Chesapeake and Ohio Canal.

Things to do recommended for couples

Seeking a romantic getaway in Cumberland? Attend the enchanting dance at Windsor Hall for a delightful evening filled with culture and entertainment. Don’t forget to visit Potomac Highland Winery, just 11.8km away, for a charming wine tasting experience amidst stunning scenery.

Things to do recommended for families

Families visiting Cumberland can explore the enchanting trails of the Great Allegheny Passage, enjoy a fun-filled day at the Allegany Museum, and take a scenic ride on the Western Maryland Scenic Railroad, offering captivating views and a delightful experience for all ages.

Things to do recommended for groups

During your group visit to Cumberland, explore the vibrant Downtown Historic District for shopping and dining, enjoy a performance at the Palace Theater for a touch of culture, and unwind with a round of golf at Maplehurst Country Club, all set against beautiful outdoor scenery.

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

If you’re travelling with a group, family, pets, or seeking extended stays, be sure to refine your search according to your key preferences. Here are some helpful Vrbo booking tips for you.

  • Traveling to Cumberland with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all these options, and more, on Vrbo.
  • Traveling to Cumberland with young kids: Travelling with young children can present its difficulties. It's essential to prioritise their comfort and safety, along with suitable amenities, like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that are suitable for families.
  • Taking your pets with you to Cumberland: For many families, a holiday wouldn’t be the same without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Cumberland: If you're searching for holiday rentals with discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. You might also want to include options such as a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay in and around Cumberland

Cumberland, Maryland, offers a delightful blend of outdoor adventures and historical charm. Explore its picturesque natural landscapes, perfect for romantic strolls or family excursions. The city's unique charm is complemented by nearby neighbourhoods, where friendly locals and trendy spots create a welcoming atmosphere. Whether you're wandering through central Cumberland or venturing into surrounding areas, you'll uncover an array of scenic vistas and captivating destinations waiting to be discovered.

  • LaVale: Nestled within the vicinity of Cumberland, LaVale is a picturesque village that offers a delightful escape into nature. Known for its scenic beauty, visitors flock here for outdoor activities and romantic getaways. The area features recreational spaces perfect for picnics and leisurely strolls, along with an arena entertainment facility that hosts various events. Nearby, you can explore a lovely lake, delve into history at local landmarks, or venture into the stunning national state park that showcases the region’s natural splendour.
  • Frostburg: Located approximately 5.6km from Cumberland, Frostburg is a charming city renowned for its breathtaking landscapes and outdoor adventures. The town is a haven for those seeking scenic views and romantic experiences. Visitors can enjoy a variety of activities, including skiing in the winter months or exploring recreational areas throughout the year. Notable attractions include a historic college university and the nearby national state park, where visitors can immerse themselves in nature and learn about the area's rich history.
  • Ridgeley: Just 1.6km away from Cumberland, Ridgeley offers a quaint and inviting atmosphere for tourists. This city attracts those who appreciate outdoor pursuits and beautiful scenery, making it a delightful spot for a romantic escape. With access to recreational areas, an arena entertainment facility, and educational venues, there's plenty to keep visitors engaged. The nearby lake and national state park offer perfect settings for exploration, while historic landmarks add a touch of charm to the local experience.

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 in July to August and October, 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 SunnyAverageSlightly Low
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 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 SunnyModerately HighAverage
November41.7°F (5.4°C)Light RainMostly SunnyAverageAverage
December35.1°F (1.7°C)Light RainMostly CloudyAverageAverage

Booking with Vrbo is simple

Looking to cut costs on your next holiday? Consider being flexible with your travel dates, as prices can change significantly. Moreover, opting for a longer stay can often result in substantial savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a hassle-free way to plan your journeys, allowing you to start new trips, continue from where you last paused, or review and arrange your itineraries. You can easily find your saved or booked properties sorted into sections for Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

The majestic setting of Cumberland is ready to explore

The area's history and churches are just some of the reasons to come on holiday to Cumberland. Travellers to this scenic city praise the casino gaming, hiking and cycling. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday 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

Are you searching for attractions to visit in the city? You'll be sure to enjoy Cumberland for its hiking and cycling. Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Cumberland a fun place to get away to. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Maplehurst Country Club (8.2 mi / 13.2 km)

Exploring the natural features in Cumberland

Travellers enjoy Cumberland for its mountain views, riverfront and lakeside setting. Whether you're looking for fun outdoor activities or just want to take in the scenery, Cumberland is a great place to get out in nature. Here are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Lake Habeeb Beaches (6.8 mi / 10.9 km)
  • Savage River (11 mi / 17.7 km)
  • Canal Place (0.3 mi / 0.6 km)
  • Lake Habeeb (6.9 mi / 11.1 km)
  • Little Allegheny Mountain (7.4 mi / 11.9 km)
  • Allegheny Passage (10.7 mi / 17.2 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 centre.

If you're travelling by train, 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 when booking a holiday rental?
When considering a holiday rental in Cumberland, Maryland, a popular area to stay is the historic downtown district. This charming neighbourhood is filled with quaint shops, delightful restaurants, and a vibrant arts scene, making it a superb base for exploring the city. One of the top attractions nearby is the Allegany Museum, where visitors can immerse themselves in the rich history of the region. Additionally, the scenic rides along the Great Allegheny Passage provide excellent opportunities for cycling and enjoying the picturesque views of the surrounding landscapes.

Another appealing area is the South End, which offers a more residential feel while still being close to key attractions. Here, you can easily access the beautiful Rocky Gap State Park, ideal for outdoor enthusiasts looking to hike, fish, or simply relax in nature. This neighbourhood typically features a variety of holiday rentals, providing options for different group sizes and budgets.
How much does it cost to rent a holiday home in Cumberland?
Prices for holiday 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 holiday 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, Maryland, the closest skiing opportunities can be found at Wisp Resort, which is located approximately 30 miles away in McHenry, Maryland. In the vicinity of Wisp Resort, travellers can find a range of holiday rentals, including cozy mountain lodges and modern chalets. Many of these properties come equipped with amenities such as spacious living areas, full kitchens, and fireplaces, ideal for warming up after a day on the slopes.

In McHenry, visitors can also explore options that offer breathtaking views of Deep Creek Lake, with some properties featuring large decks or balconies, great for enjoying the scenic surroundings. Many rentals here cater to families or larger groups and may include additional amenities like hot tubs, game rooms, and access to nearby hiking trails for off-slope activities.
What is the most popular type of holiday rental accomodation in Cumberland?
In Cumberland, a variety of holiday rental options are available, with holiday houses, apartments, cottages, cabins, and campsites all being quite popular. Numerous holiday houses can be found throughout the town, often featuring multiple bedrooms, fully equipped kitchens, and outdoor spaces for relaxation. The apartments tend to be centrally located, offering easy access to local attractions and amenities. Cottages provide a quaint and charming experience, typically set in more scenic areas, while cabins offer a rustic retreat, making them great for nature lovers wanting to explore the surrounding landscapes. For those seeking a more adventurous stay, several campsites are situated near the area's parks and recreational areas.
Are there any family house rentals in Cumberland?
In Cumberland, Maryland, there are several family-friendly house rentals, with around 14 options available throughout the area. Neighbourhoods such as the historic downtown and the scenic areas near the Potomac River provide a variety of spacious homes suited for families. Many of these properties come equipped with essential amenities like full kitchens, inviting living rooms, and outdoor spaces for children to play.
Can I rent a holiday home with a pool or hot tub in Cumberland?
In Cumberland, Maryland, there are several holiday homes available for rent that feature pools and hot tubs, making it an appealing destination for travellers seeking relaxation. The area boasts a variety of neighbourhoods, each offering great experiences. Properties in the downtown area often provide easy access to local attractions, while those located in more suburban settings might offer a quieter retreat surrounded by nature.
Can I find long-stay holiday rentals in Cumberland?
A long-stay holiday rental in Cumberland is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Cumberland?
In Cumberland, there are several pet-friendly house rentals available, offering a variety of amenities to ensure a comfortable stay for travellers with pets. Many of these properties come equipped with spacious backyards, ideal for pets to roam and play, as well as modern conveniences like fully equipped kitchens and comfortable living areas.

The city is surrounded by beautiful natural landscapes, including the scenic Great Allegheny Passage, which provides ample opportunities for outdoor activities such as hiking and biking. This trail is particularly welcoming for those with pets, allowing for enjoyable walks and excursions.
Are there any remote work holiday rentals in Cumberland?
In Cumberland, Maryland, there are several remote work-friendly holiday rentals available, with around 17 options to choose from. These properties are well-equipped to cater to the needs of remote workers, typically featuring dedicated workspaces that include desk chairs, desks, and computer monitors. Additionally, high-speed Wi-Fi is commonly provided, ensuring a reliable internet connection for productivity. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Cumberland holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Cumberland with parking available—perfect for families or travellers 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 holiday rental amenities include fully equipped kitchens featuring essential cookware, dishware, and utensils, as well as modern appliances like microwaves, refrigerators, and stovetops. These amenities provide guests with the convenience of preparing their own meals, making it an ideal choice for those seeking a home-like experience during their stay in this charming city.
When is the best time to visit Cumberland for a holiday rental?
September is the most popular time to visit Cumberland, a charming city located in the picturesque Appalachian Mountains. This month falls within the peak season, which spans from August to October, and is superb for travellers looking to enjoy a variety of outdoor activities. As the summer heat begins to fade, visitors can explore the scenic trails of the Great Allegheny Passage, immerse themselves in the vibrant local arts scene, or take leisurely strolls through the historic downtown area.

During September, temperatures are generally mild, averaging in the low 20s Celsius, making it an ideal time for sightseeing and outdoor pursuits. The stunning autumn foliage begins to emerge, painting the landscape in rich hues of red, orange, and gold, creating a breathtaking backdrop for both photography and leisurely drives.

For those seeking a more budget-friendly experience, May can be an excellent time to visit. During this month, you can enjoy the early blooms of spring and a quieter atmosphere, superb for peaceful exploration. The natural beauty of the surrounding area is particularly captivating, and the mild weather allows for comfortable hiking and biking.
How early should I book a Cumberland holiday rental?
Book your Cumberland holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Cumberland?
In Cumberland, Maryland, visitors can explore a variety of attractions that showcase the area's rich history and natural beauty. The historic downtown area features charming shops and local eateries, making it a lovely spot to wander and enjoy the local culture. Nearby, the C&O Canal National Historical Park offers scenic views and recreational opportunities such as hiking and cycling along the canal towpath, which is great for those who enjoy outdoor activities.

The Allegany Museum, located in the heart of Cumberland, provides insight into the region's history and heritage, with exhibits ranging from the Civil War to the area's coal mining past. For those interested in the great outdoors, the nearby Rocky Gap State Park offers stunning landscapes, a lake for fishing, and trails for hiking, ensuring a variety of options for nature enthusiasts.
Can I change or cancel my Cumberland home rental booking on Vrbo?
To find Cumberland holiday 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 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 travellers 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 cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, 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 organising 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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