Winter holiday lettings

We found 52 holiday rentals — enter your dates for availability

Discover a selection of 12 homes, 24 cabins and other holiday rentals in Winter that are perfect for your trip. Holiday homes offer the best amenities for your family, friends or furry companion, such as air conditioning and cable TV. No matter what you're looking for, you'll be sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

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Find the perfect holiday rental for your Winter getaway

Learn about the unique charm of Winter with a stay in a holiday home rental. This city has something for everyone. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Winter

Do you want to discover attractions to see while you're in town? Venture out of your holiday home and experience everything that makes Winter a fun spot to go on holiday. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • The Tee-Away Golf Course and Supper Club (23.9 mi / 38.4 km)
  • Park Falls Country Club (29.4 mi / 47.3 km)
  • Barker Lake Golf Course (6.8 mi / 10.9 km)
  • Wildwood Marshes Golf Course (17.9 mi / 28.9 km)
  • Josie Creek County Park (21.1 mi / 33.9 km)
  • St Croix Rod Company (28.4 mi / 45.8 km)

Exploring the natural landscape of Winter

Whether you're an active traveller or just want to spend some time taking in the scenery, Winter is a great place to get outside. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Lake Winter (1.2 mi / 2 km)
  • Lake Chippewa (6.4 mi / 10.4 km)
  • Callahan Lake (16.1 mi / 25.9 km)
  • Clear Lake (18.5 mi / 29.7 km)
  • Tiger Cat Flowage (18.7 mi / 30 km)
  • Teal Lake (18.9 mi / 30.4 km)

Frequently asked questions

What is the best area to stay in Winter when booking a holiday rental?
When considering a holiday rental in Winter, Wisconsin, a fantastic area to stay is near the charming downtown district. This location offers a delightful mix of convenience and local character. Staying here places you within easy reach of several attractions, such as the scenic Winter Park, which is great for outdoor enthusiasts looking to enjoy activities like skiing and snowshoeing in winter, or hiking during the warmer months. The nearby Namekagon River is also a wonderful spot for those interested in fishing or kayaking, providing a serene backdrop for relaxation.

Another appealing option is to find a rental close to the Chequamegon National Forest. This expansive area is renowned for its stunning natural beauty and extensive trails, making it a haven for nature lovers and hikers. The forest is particularly enchanting in winter when it transforms into a snowy wonderland, ideal for winter sports enthusiasts.
How much does it cost to rent a holiday home in Winter?
Prices for holiday rentals in Winter 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 Winter 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 Winter holiday house rentals?
You can find great discounts on house rentals in Winter 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 Winter?
For renting a beach house in Winter, Wisconsin, focus on the scenic areas surrounding the many lakes in the region. The area around the scenic Round Lake is particularly appealing, offering properties with direct water access and stunning views. Many of these rentals come equipped with amenities such as private docks, outdoor fire pits, and spacious decks superb for gatherings, allowing families and groups to enjoy summer activities like swimming, fishing, and boating.

Another excellent option is the area near the Tuscobia State Trail, which not only provides a beautiful natural setting but also easy access to hiking and biking paths. Here, you can find charming cabins and cottages that often feature rustic interiors, modern kitchens, and cozy living spaces with fireplaces, ideal for relaxing after a day outdoors.
Where are the best Winter ski resort rentals?
For ski resort rentals in Winter, Wisconsin, the best options are typically found around the nearby area of Cable and the surrounding Chequamegon National Forest. These locations provide easy access to ski trails and snowmobiling routes, making them ideal for winter sports enthusiasts. In Cable, travellers can find a variety of cabin rentals that often come with rustic charm and modern amenities. Many properties feature cosy fireplaces, fully equipped kitchens, and outdoor decks, allowing guests to enjoy the natural beauty of the snow-covered landscape.

Additionally, some lodges in the area offer communal facilities such as hot tubs and sauna access, superb for unwinding after a day on the slopes. Staying in Cable also provides proximity to the local shops and restaurants, where visitors can sample regional cuisine and enjoy a warm drink after a day of skiing.
What is the most popular type of holiday rental accomodation in Winter?
In Winter, cabins are the most popular type of holiday rental, with about 25 available in the area. These rustic lodgings are often situated near the beautiful natural surroundings, offering travellers a peaceful retreat. Most cabins come equipped with essential amenities such as fully functional kitchens, comfortable living areas, and outdoor spaces like decks or fire pits, superb for enjoying the crisp air and scenic views.
Are there any family house rentals in Winter?
In Winter, Wisconsin, there are numerous family-friendly holiday rentals available, with around 31 options to choose from. This charming area is great for families looking to enjoy outdoor activities together, especially during the winter months when snow sports are in full swing. Many of these homes come equipped with spacious living areas, full kitchens for preparing meals, and often feature amenities like game rooms or outdoor fire pits for evening gatherings.
Can I find long-stay holiday rentals in Winter?
A long-stay holiday rental in Winter 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 Winter?
In Winter, Wisconsin, there are numerous pet-friendly house rentals available, providing a welcoming environment for those travelling with their furry companions. Many of these rentals are equipped with amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces, making them ideal for families or groups looking for a comfortable stay.
Are there any remote work holiday rentals in Winter?
In Winter, Wisconsin, there are numerous options for remote work holiday rentals, with around 33 available in the area. Travellers can expect properties that are well-equipped for productivity, featuring amenities such as high-speed Wi-Fi, dedicated desk spaces, and comfortable desk chairs. Many rentals also include computer stations and monitors, making it easy to set up a functional workspace. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Winter holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Winter 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 Winter?
In Winter, Wisconsin, popular holiday rental amenities typically include fully equipped kitchens, which are essential for preparing meals during a stay. Many rentals feature microwaves, stovetops, and necessary cookware, dishware, and utensils, allowing guests to enjoy the convenience of home cooking. This makes the area's rentals particularly appealing for families or groups looking to gather and share meals after a day of exploring the beautiful natural surroundings.
When is the best time to visit Winter for a holiday rental?
The best time to visit Winter, Wisconsin, is during the summer months from June to August, when the area comes alive with outdoor activities and vibrant community events. This peak season attracts travellers looking to enjoy the beautiful natural surroundings, including fishing, hiking, and boating in the pristine lakes that define this charming region.

July is particularly popular, offering warm temperatures averaging around 25°C, ideal for exploring the great outdoors and participating in local festivities. The long days provide ample time for sightseeing, whether you're wandering through the lush forests or soaking up the sun by the water.

For those seeking a more budget-friendly experience, consider planning your visit in March. This month, while quieter, offers its own unique charm with the potential for late-season winter sports and a chance to appreciate the peaceful, snow-covered landscape.
How early should I book a Winter holiday rental?
Book your Winter 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 Winter home rental booking on Vrbo?
To find Winter 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 Winter 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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