Cumberland holiday lettings

We found 34 holiday rentals — enter your dates for availability

Discover a selection of 8 homes 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:24 Oct - 31 Oct
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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.

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.

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

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.

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 / 10.5 km)
  • Rocky Gap Golf Resort (6.7 mi / 10.8 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)
  • Lake Habeeb (6.9 mi / 11.1 km)
  • Savage River (11 mi / 17.7 km)
  • Canal Place (0.3 mi / 0.6 km)
  • Little Allegheny Mountain (7.4 mi / 11.9 km)
  • Chesapeake and Ohio Canal National Historical Park (17.8 mi / 28.7 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?
Among the more sought-after destinations to book your holiday rental in Cumberland is LaVale. Set up home here and have fun visiting its must-see attractions, including La Vale Tollgate House and Country Club Mall.
What is the most popular type of holiday rental accommodation in Cumberland?
The most in-demand types of holiday rentals in Cumberland are houses. Ready for more choices? Vrbo has numerous options to match the unique needs of our guests, so you'll see holiday properties in all sizes, and for all budgets. The perfect home away from home is waiting for you — snap up yours today.
How much does it cost to rent a holiday rental in Cumberland?
Length of stay, property type and season are some factors that can affect the price of a holiday home. Simply click on your dates of travel to find your dream escape. From comfy cottages to sprawling villas, all Vrbo holiday rentals provide incredible value.
How much does it cost to rent a beach house in Cumberland?
When you travel and the size and style of the property will influence how much you'll pay for your beachside escape. Put in your Cumberland travel dates to see all your options on Vrbo. Can't live without a hot tub? Use the filters to choose the features and amenities you want in your rental.
Are there pet-friendly holiday rentals in Cumberland?
Pack a tug toy and treats for your puppy dog because Cumberland has five holiday homes that throw out the welcome mat to doggie guests. Let your furriest pal join in on the family trip at one of our pet-friendly holiday rentals on Vrbo. Simply enter your destination and travel dates, then check our "Pets allowed" filter box.
What are popular rental amenities in Cumberland?
High-speed internet services, an oven and winery tours rank as the most popular rental amenities in Cumberland. Whether you plan to travel on your own, with your sweetheart or a group of friends, Vrbo can help you find a holiday rental that fits your tastes with all the conveniences you're looking for.
Are there large group holiday rentals in Cumberland?
Take your pick of three Vrbo properties in Cumberland that can host a group of five or more guests. You'll get all the space and privacy you need to relax with the people you're holidaying with — and no one else.
Are there holiday rentals in Cumberland that welcome kids?
Bring the whole group together for an epic adventure in Cumberland at one of our five family-friendly holiday homes. Many of these stays offer amenities that are perfect for getaways with the little ones, like laundry facilities, extra bedrooms and entertainment areas. Just click on the "Properties good for families" filter and book your favourite.
What are the top attractions for families in Cumberland?
You'll find lots of cool things to see and do with the family in Cumberland, such as:

  • Western Maryland Railroad Station
  • Tri-State Zoological Park
  • Allegany Museum

Can I find two-bedroom holiday rentals in Cumberland?
Pick from two two-bedroom holiday properties in Cumberland. Settle the kids into the second room or fill it with a couple of your besties. There's ample space for whoever's lucky enough to be joining your adventure.
How can I find holiday rentals with air conditioning in Cumberland?
Select your travel dates and then make use of our filters to search for holiday rentals with air conditioning in Cumberland on Vrbo. With four air-conditioned properties on offer here, you can enjoy a comfy and cool stay.
How old do you have to be to rent a holiday rental in Cumberland?
The minimum required age is generally 16, 18 or 21. It can differ between properties on Vrbo, so check the rules of your preferred Cumberland holiday rental before booking your trip.
How long can I rent a holiday rental in Cumberland for?
It's down to the Cumberland property. To view a list of options offering extended stays, simply enter your travel dates and guest number into Vrbo. Enjoy having the entire property to yourself, along with home comforts such as air conditioning, a kitchen and an outdoor space where your little ones can play. Keep your eyes peeled for long-term stays that offer discounted weekly or monthly prices.

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