Cumberland holiday homes

We found 47 holiday rentals — enter your dates for availability
Discover a selection of 7 homes and other holiday rentals in Cumberland that are perfect for your trip. Holiday rentals offer the best amenities for you and your friends, family or even pets, such as Wi-Fi and a washer and dryer. You'll be sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

The friendly area of Cumberland awaits your stay

Enjoy the art galleries and other features of Cumberland. This welcoming city has many special qualities. 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 Cumberland

Are you searching for attractions to visit during your stay? Venture out of your cosy holiday rental and check out everything that makes Cumberland a fun spot to go on holiday. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Turtleback Golf Club (12.1 mi / 19.5 km)
  • Sunset View Golf Course (22.2 mi / 35.8 km)
  • Spooner Golf Club (23.1 mi / 37.1 km)
  • Rolling Oaks Golf Course (11.7 mi / 18.9 km)
  • Siren National Golf Club (25.7 mi / 41.3 km)
  • Clover Meadow Winery (16.7 mi / 26.9 km)

Exploring the natural landscape of Cumberland

Whether you're an adventurous traveller or just want to appreciate the scenery, Cumberland is a great place to spend some time outside. Here are some of the area’s most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Butternut Lake (8.8 mi / 14.2 km)
  • Horseshoe Lake (9.1 mi / 14.7 km)
  • Silver Lake (11.2 mi / 18 km)
  • Big Round Lake (13.6 mi / 21.9 km)
  • Cedar Side Walking Trail (13.7 mi / 22 km)
  • Rice Lake City Park (14.1 mi / 22.6 km)

Frequently asked questions

What is the best area to stay in Cumberland when booking a holiday rental?
When looking for the best area to stay in Cumberland, Wisconsin, you'll find that the downtown area offers a charming atmosphere with a variety of holiday rental options. This neighbourhood is not only convenient for accessing local shops and restaurants, but it also provides a delightful sense of community. The properties in this area range from cosy cabins to comfortable cottages, making it an appealing choice for families or couples alike.One of the top attractions nearby is the picturesque Beaver Dam Lake, which is great for fishing, boating, and enjoying scenic walks along the shore. Additionally, the quaint downtown features local boutiques and cafes where you can savour the local flavours. For those interested in outdoor activities, the nearby Rice Lake area provides ample opportunities for hiking and exploring the natural beauty of Wisconsin.
Where are the best areas for renting a beach house in Cumberland?
For renting a beach house in Cumberland, the area surrounding Lake Cumberland is an excellent choice. This picturesque lake offers numerous private beach accesses and tranquil waterfront views, superb for a relaxing getaway. Visitors can find a range of properties, including spacious lakeside cabins and charming cottages, many of which come with amenities such as outdoor decks, barbecue grills, and private docks for boating or fishing.The nearby town of Cumberland also provides convenient access to local shops and restaurants, ideal for travellers. Many rentals in this area often feature family-friendly amenities, such as game rooms and access to nearby hiking trails, making it a great spot for those who enjoy outdoor activities.
Where are the best Cumberland ski resort rentals?
For skiing in Cumberland, Wisconsin, the best options for rentals are located in the nearby area of the Turtle Lake and Rice Lake. These locations provide convenient access to local ski hills and winter sports activities. In Turtle Lake, you can find a variety of holiday homes and cabins that often come equipped with amenities such as full kitchens, living areas with fireplaces, and outdoor spaces for enjoying the crisp winter air.In Rice Lake, properties typically offer comfortable accommodations suitable for families or groups, featuring amenities like hot tubs for relaxing after a day on the slopes and proximity to local dining and shopping options. Many rentals in this area also provide easy access to cross-country skiing trails and snowmobile routes, allowing for a full winter experience.Moreover, the natural beauty of the surrounding landscapes offers opportunities for outdoor adventures beyond skiing, with ample trails for hiking and snowshoeing.
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 around 40 available in the area. These properties are often found in scenic locations, providing ample space for families or groups, and typically feature multiple bedrooms, fully equipped kitchens, and outdoor areas for relaxation. Additionally, there are about 16 cabins and 12 cottages, which offer a more rustic experience, ideal for those looking to immerse themselves in nature. Condos are also available, though in smaller numbers, offering a more compact option with essential amenities.
Are there any family house rentals in Cumberland?
In Cumberland, Wisconsin, there are some family-friendly house rentals available, with around 14 options to consider. This charming town offers a serene atmosphere, making it an ideal location for families seeking a relaxing getaway. Many of the properties feature spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces for children to play or for families to enjoy barbecues.Visitors will find amenities such as Wi-Fi to stay connected and comfortable furnishings throughout. The nearby lakes and parks provide ample opportunities for outdoor activities, including fishing, hiking, and swimming, ensuring that families have plenty of options for fun and exploration.
Are there pet-friendly house rentals in Cumberland?
In Cumberland, Wisconsin, there are several pet-friendly house rentals available, providing a great option for travellers who wish to bring their furry companions along. Many of these holiday homes are situated near the scenic beauty of the area, offering amenities such as spacious yards, outdoor decks, and fully equipped kitchens. This makes them ideal for families or groups looking for comfort and convenience during their stay.The vicinity is also known for its proximity to lovely outdoor spaces, including nearby parks and lakes that are pet-friendly. These areas often feature walking trails and open spaces where pets can play and explore.
Are there any remote work holiday rentals in Cumberland?
In Cumberland, Wisconsin, there are numerous remote work-friendly holiday rentals available, with around 68 options for travellers seeking a conducive workspace. Many of these properties come equipped with essential amenities such as reliable Wi-Fi, ensuring a smooth working experience. Guests can expect various accommodations, ranging from cosy cabins to spacious homes, many of which feature dedicated workspaces, free internet access, and comfortable living areas.The town is surrounded by picturesque lakes and forests, providing an inspiring backdrop for remote work. After hours, guests can explore local attractions such as the scenic parks and trails for outdoor activities or enjoy the peaceful charm of the town. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Cumberland?
In Cumberland, popular holiday rental amenities include kitchens, which allow guests to prepare their own meals, and decks or patios that provide outdoor space for relaxation. Many rentals also feature fireplaces, superb for cozy evenings, along with essential appliances such as blenders for smoothies and coffee or tea makers for a warm beverage.
When is the best time to visit Cumberland for a holiday rental?
The most popular time to visit Cumberland is during the summer months, particularly July, when the vibrant setting draws visitors eager to enjoy the beautiful outdoors. This peak season, which spans from June to August, offers a fantastic blend of activities, including boating, fishing, and hiking, all while soaking in the pleasant weather and lush scenery.Cumberland typically enjoys warm temperatures during this time, often reaching highs in the low 30s Celsius. This makes it ideal for outdoor adventures, whether you're exploring the scenic trails or relaxing by one of the area's many lakes. Visitors can also partake in local events and festivals that add to the lively summer spirit.If you're looking for a more budget-friendly option, consider planning your visit in December. While this is the low season, you can embrace the charm of the winter landscape and enjoy a peaceful retreat away from the usual crowds, indulging in cozy indoor activities or winter sports.Ultimately, the best time to book a holiday rental in Cumberland depends on your preference for lively summer adventures or the tranquil beauty of winter.
What are the top attractions in Cumberland?
In Cumberland, visitors can enjoy a range of attractions that highlight the area's natural beauty and small-town charm. The Crystal Lake area is particularly popular, offering opportunities for swimming, fishing, and boating during the warmer months, while in winter, it becomes a serene spot for ice fishing and snowshoeing. Nearby, the scenic trails of the Chequamegon National Forest provide excellent hiking and biking options, allowing for exploration of the region's diverse flora and fauna.The main street in Cumberland features quaint shops and local eateries that reflect the town's friendly atmosphere. The annual events, such as the Cumberland Arts and Crafts Fair, showcase local talent and create a vibrant community spirit.
Are all fees included in the Cumberland holiday homes prices shown on Bookabach?
Bookabach 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?
Bookabach 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 Bookabach, 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 Bookabach?
To find Cumberland holiday rentals with free cancellation, just use Bookabach'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, Bookabach 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 Bookabach?
Bookabach'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 Bookabach 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. Bookabach offers something for every taste and budget, from affordable homes in Cumberland to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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 Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

More holiday ideas