Cumberland holiday rentals

We found 37 holiday rentals — enter your dates for availability
Discover a selection of 11 homes, 12 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.

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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)

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)
  • 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)
  • Little Allegheny Mountain (7.4 mi / 11.9 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 near the Historic Downtown district. This charming neighbourhood is rich in history and offers a variety of attractions, including the beautiful Gordon-Roberts House and the Allegany Museum, which showcases the local heritage. The vibrant setting of Downtown Cumberland is great for those who enjoy exploring unique shops, delightful cafes, and local eateries.Another fantastic option is the area around the C&O Canal National Historical Park, which provides access to stunning outdoor activities. Visitors can enjoy hiking, biking, and picturesque views along the canal, making it a great choice for nature lovers. This area also boasts a number of holiday rentals, ensuring you have a comfortable place to unwind after a day of exploration.In both these neighbourhoods, you'll find a variety of properties that cater to different tastes and budgets, allowing you to immerse yourself in the local culture while enjoying the comforts of home.
Where are the best Cumberland ski resort rentals?
For skiing near Cumberland, the closest resort is in the nearby Wisp Resort, located in McHenry, Maryland, roughly a 30-minute drive from Cumberland. In the McHenry area, travellers can find a variety of holiday rentals, including cosy cabins and chalets that cater to winter sports enthusiasts. Many of these properties feature amenities such as fully equipped kitchens, spacious living areas with fireplaces, and outdoor decks with stunning views of the surrounding mountains.In addition to the convenience of being near the ski slopes, these rentals often provide easy access to local attractions such as Deep Creek Lake, which is great for both summer and winter activities. Many cabins come with hot tubs, great for relaxing after a day on the slopes, and some may even offer game rooms or access to community facilities, enhancing the overall experience for families and groups.The nearby town of Oakland also presents additional options for accommodations, with charming lodges and inns that provide a more intimate setting. Here, guests can enjoy local dining experiences and explore the picturesque scenery of Garrett County.
What is the most popular type of holiday rental accomodation in Cumberland?
In Cumberland, holiday houses are the most popular type of holiday rental, with about 28 available across various neighbourhoods. These properties typically offer ample space with multiple bedrooms, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups. Additionally, there are around 24 apartments scattered throughout the city, providing a more compact option for travellers. Many of these apartments come with amenities such as modern kitchens and laundry facilities. For those seeking a charming getaway, several cottages and cabins are also available, offering a rustic experience with access to nature. Campsites can be found as well, suiting outdoor enthusiasts.
Are there any family house rentals in Cumberland?
In Cumberland, Maryland, there are numerous family-friendly holiday rentals available, with around 15 options scattered throughout the area. This charming city offers a rich history and beautiful natural surroundings, making it an excellent choice for families. Many of these homes feature spacious living areas, multiple bedrooms for ample accommodation, and fully equipped kitchens where families can prepare meals together.Visitors can enjoy outdoor spaces as well, often including gardens or patios that provide a ideal setting for children to play. Additionally, amenities such as Wi-Fi and laundry facilities are commonly found, ensuring a convenient and comfortable stay.Cumberland is close to points of interest like the scenic Great Allegheny Passage, ideal for biking and hiking enthusiasts, and the historic downtown area, which offers shops and local dining options.
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, providing a refreshing escape for travellers. The area offers a mix of charming neighbourhoods, including the picturesque downtown area, where historic architecture meets modern amenities. Many of these rentals come equipped with private pools, hot tubs, and outdoor spaces where guests can relax and enjoy the scenic views of the surrounding Appalachian Mountains.Expect amenities such as fully equipped kitchens for home-cooked meals, spacious living areas for family gatherings, and Wi-Fi for keeping connected during your stay. Some properties may also include features like barbecue grills and outdoor seating, making them superb for entertaining or enjoying a quiet evening under the stars.
Are there pet-friendly house rentals in Cumberland?
In Cumberland, there are several pet-friendly house rentals available that cater to travellers with furry companions. The city is surrounded by beautiful natural scenery, making it an excellent choice for those looking to explore the outdoors with their pets. Many of the holiday homes in the area offer amenities such as spacious yards, fully equipped kitchens, and comfortable living spaces, ensuring a pleasant stay for both humans and pets.Cumberland's location also provides access to nearby parks and recreational areas, where you can enjoy walks and outdoor activities with your pet. The scenic C&O Canal National Historical Park is not far away, offering trails that are ideal for hiking and enjoying nature.
Are there any remote work holiday rentals in Cumberland?
In Cumberland, Maryland, there are numerous remote work holiday rentals available, with around 64 options to choose from. This charming city, located in the Appalachian Mountains, offers a variety of accommodations suitable for those looking to work remotely while enjoying a change of scenery. Many properties come equipped with essential amenities such as free Wi-Fi, dedicated workspaces, and comfortable desk chairs, ensuring a productive environment.Travellers can expect a range of options, including cozy apartments and spacious houses that provide both comfort and functionality. The proximity to local attractions, such as the historic downtown area with its shops and eateries, adds to the appeal, allowing for leisurely breaks amidst work commitments. The surrounding natural beauty, including the scenic Great Allegheny Passage, offers ample opportunities for outdoor activities, making it an ideal location for remote workers seeking both productivity and relaxation. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Cumberland?
In Cumberland, popular rental amenities often include kitchens, allowing guests to prepare their own meals during their stay. Many properties feature decks or patios, providing outdoor spaces for relaxation and enjoying the scenic views. A coffee and tea maker is typically available, great for those who enjoy a warm beverage in the morning. Onsite parking is also common, ensuring convenience for travellers with vehicles. Additionally, some rentals may offer porches or lanais, enhancing the overall experience by providing extra space to unwind outdoors.
When is the best time to visit Cumberland for a holiday rental?
September is the most popular time to visit Cumberland, as the summer crowds begin to dwindle and the region showcases its natural beauty in a more tranquil setting. The peak season runs from August to October, and during this time, visitors can enjoy a range of outdoor activities, including hiking, biking, and exploring the scenic C&O Canal National Historical Park.With temperatures typically ranging from 10 to 25 degrees Celsius in September, the weather is pleasantly mild, making it ideal for sightseeing and enjoying leisurely strolls through the charming downtown area. This month also features various local events and festivals, allowing travellers to immerse themselves in the vibrant community spirit.For those looking for a more budget-friendly option, May offers a quieter experience while still presenting the opportunity to appreciate the natural beauty of the area as spring blossoms. The milder weather in early spring can be quite refreshing, providing a peaceful backdrop for outdoor activities and exploration without the hustle and bustle of peak season.Ultimately, your choice of when to visit Cumberland will hinge on whether you prefer the lively option of the late summer and early autumn months or the serene beauty of the springtime.
What are the top attractions in Cumberland?
Cumberland, Maryland, offers a variety of attractions that highlight its rich history and natural beauty. The historic downtown area features the Allegany Museum, which showcases the region's history, including its industrial past and the importance of the Chesapeake and Ohio Canal. Nearby, the iconic C&O Canal National Historical Park provides opportunities for hiking, cycling, and enjoying scenic views along the canal.For outdoor enthusiasts, the nearby Rocky Gap State Park is a must-visit, offering a beautiful lake, hiking trails, and picnic areas, great for family outings. The park also features a golf course and opportunities for fishing and camping.Cumberland is also known for its vibrant arts scene, with venues such as the Maryland Theatre hosting various performances and events throughout the year.
Are all fees included in the Cumberland holiday homes prices shown on Stayz?
Stayz 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.
Are there any Cumberland holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Cumberland holiday homes?
You can find great discounts on holiday homes in Cumberland on Stayz, 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.
Can I change or cancel my Cumberland holiday home booking on Stayz?
To find Cumberland holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Cumberland?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Cumberland holiday home?
Book your Cumberland holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Cumberland?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Cumberland to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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