Cumberland holiday lettings

We found 44 holiday rentals — enter your dates for availability

Discover a selection of 10 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.

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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)
  • Spooner Golf Club (23.1 mi / 37.1 km)
  • Rolling Oaks Golf Course (11.7 mi / 18.9 km)
  • Clover Meadow Winery (16.7 mi / 26.9 km)
  • Luck Golf Course (21.4 mi / 34.5 km)
  • Sunset View Golf Course (22.2 mi / 35.8 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)
  • Little Horseshoe Lake (11.9 mi / 19.2 km)
  • Cedar Side Walking Trail (13.7 mi / 22 km)
  • Rice Lake City Park (14.1 mi / 22.6 km)
  • McKenzie Lake (14.7 mi / 23.7 km)

Frequently asked questions

What is the best area to stay in Cumberland when booking a holiday rental?
When considering a holiday rental in Cumberland, Wisconsin, the downtown area is an excellent choice. This charming neighbourhood offers a delightful mix of local shops, eateries, and easy access to the scenic beauty of the surrounding lakes. Staying here places you within walking distance of the vibrant Cumberland area, where you can explore unique boutiques and enjoy delicious meals at local restaurants.

Another appealing option is the area around Beaver Dam Lake. This picturesque location is superb for those who enjoy outdoor activities. The lake provides opportunities for fishing, boating, and swimming, making it a popular spot for families and nature enthusiasts alike. Numerous holiday rentals can be found here, offering stunning views and a tranquil atmosphere.

For those interested in history and culture, the vicinity of the Cumberland Historical Society is also worth considering. Here, you can learn about the rich heritage of the area and appreciate local art. The combination of historical charm and natural beauty makes this neighbourhood a wonderful place to stay.
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 areas for renting a beach house in Cumberland?
For renting a beach house in Cumberland, Wisconsin, the area surrounding the picturesque Beaver Dam Lake is highly recommended. This serene location boasts a variety of holiday rentals that provide direct access to the sandy shores and tranquil waters, making it great for swimming, fishing, and boating. Properties in this area often come equipped with amenities such as private docks, outdoor grills, and spacious patios for enjoying the views.

Additionally, the nearby Turtle Lake offers another charming option for travellers seeking a lakeside retreat. Here, you can find lakeside cabins and cottages that feature amenities like fire pits, kayaks, and fully stocked kitchens for self-catering. Many of these properties are designed for family gatherings, with ample space for outdoor activities and relaxation by the water.
Where are the best Cumberland ski resort rentals?
For renting ski resort accommodations near Cumberland, Wisconsin, the closest ski area is the Christie Mountain ski resort, located approximately a 30-minute drive away. In the vicinity of Cumberland, travellers should consider options in the nearby town or even along the scenic Turtle Lake area, where various holiday rentals can be found.

Properties in these areas typically include chalets and cabins, often equipped with essential amenities such as kitchens for self-catering, cosy living areas for relaxation, and sometimes outdoor spaces for enjoying the winter scenery. Many rentals cater to families or groups, offering multiple bedrooms and communal spaces to unwind after a day on the slopes.
What is the most popular type of holiday rental accomodation in Cumberland?
In Cumberland, holiday houses are the most popular type of rental, with about 10 available throughout the area. These houses typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups. Alongside holiday houses, there are several cabins and cottages that offer a rustic charm, often set in tranquil surroundings, superb for those looking to immerse themselves in nature. Condos are also available in the area, providing a more modern accommodation option with amenities such as pools and fitness centres.
Are there any family house rentals in Cumberland?
In Cumberland, Wisconsin, there are numerous family-friendly house rentals available—specifically, around 14 options to choose from. The area is known for its beautiful lakes and outdoor activities, making it a superb destination for families looking to enjoy nature together. Many of these homes offer spacious living areas, fully equipped kitchens to prepare family meals, and outdoor spaces ideal for children to play and explore.
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, making it an excellent destination for travellers with pets. Many of these holiday homes are situated near beautiful lakes, offering stunning views and easy access to outdoor activities. Expect amenities such as spacious backyards, modern kitchens, and cozy living areas, which create a welcoming environment for both guests and their furry companions.
Are there any remote work holiday rentals in Cumberland?
In Cumberland, Wisconsin, there are several remote work holiday rentals available, with around 17 options to choose from. This charming area offers a serene environment great for balancing work and relaxation. Many of the properties are equipped with essential amenities for remote work, including Wi-Fi, dedicated desk spaces, and comfortable chairs, ensuring a productive stay. 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, which are a common feature in many properties. Travellers can expect cookware, dishware, and utensils to make meal preparation straightforward. Additionally, most rentals come with microwaves and refrigerators, ensuring guests have the necessary appliances for convenience during their stay.
When is the best time to visit Cumberland for a holiday rental?
July is the most popular time to visit Cumberland, Wisconsin, as families and outdoor enthusiasts flock to the area during the summer months from June to August. This peak season is characterised by warm weather, with average temperatures reaching the high 20s Celsius, making it great for a variety of outdoor activities such as boating, hiking, and fishing in the beautiful surrounding lakes and forests.

During this vibrant time, visitors can engage in local events and festivals, enjoying the lively community atmosphere. The long days and pleasant evenings create an ideal setting for sightseeing and outdoor dining, where you can savour local cuisine while taking in the stunning natural views.

For those seeking a more budget-friendly option, consider planning your visit in December. While this is considered the low season, it offers a unique charm with winter activities like snowmobiling and ice fishing. The serene landscape covered in snow provides an entirely different perspective of Cumberland, great for cosy getaways.
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.
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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