Winter holiday lettings

We found 55 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)
  • 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)
  • Park Falls Country Club (29.4 mi / 47.3 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)
  • Black Dan Lake (6.6 mi / 10.6 km)
  • Headflyer Island (8.2 mi / 13.2 km)
  • Callahan Lake (16.1 mi / 25.9 km)
  • Tiger Cat Flowage (18.7 mi / 30 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, the area around the picturesque Chippewa Flowage is highly recommended. This stunning region is renowned for its beautiful natural surroundings and offers a range of outdoor activities such as fishing, boating, and hiking. The Chippewa Flowage itself is a popular attraction, boasting over 15,000 acres of water and numerous islands to explore, making it a superb spot for nature enthusiasts.

Another appealing neighbourhood is the area near the Chequamegon National Forest, where visitors can engage in the beauty of Wisconsin's woodlands. This forest is a fantastic destination for hiking, birdwatching, and enjoying the serenity of nature. With several holiday rentals available in both of these areas, guests can find comfortable accommodations that suit their needs while being conveniently located near these top attractions.
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 Winter ski resort rentals?
For renting ski accommodations in Winter, Wisconsin, the area surrounding the local ski hills is ideal for travellers seeking winter sports. The nearby Telemark Resort offers a range of holiday rentals, including spacious cabins and chalets that can accommodate families or groups. Many of these properties feature amenities such as fully equipped kitchens, private decks, and fireplaces, providing a cozy atmosphere after a day on the slopes.

In addition to Telemark, the area around Winter is home to various charming lodges and rustic cabins that provide direct access to cross-country skiing trails and snowshoeing routes. These rentals often come with essential comforts like central heating, Wi-Fi, and outdoor fire pits, making them superb for relaxing evenings under the stars.

The surrounding landscape also offers opportunities for ice fishing and snowmobiling, with several rental properties located near trails for these activities.
What is the most popular type of holiday rental accomodation in Winter?
In Winter, cabins are the most popular type of holiday rental, with approximately 96 available throughout the area. These cabins typically offer a rustic charm and are equipped with amenities such as fully equipped kitchens, comfortable living areas, and outdoor spaces for enjoying the natural surroundings. Many are located in tranquil settings, providing a superb retreat for those looking to relax and connect with nature.

In addition to cabins, there are around 40 holiday houses available, which cater to larger groups or families seeking more space. These homes often feature multiple bedrooms, spacious living areas, and sometimes outdoor facilities like decks or fire pits for evening gatherings. Cottages also provide a quaint option, with about 20 available, offering a cosy atmosphere ideal for couples or small families.
Are there any family house rentals in Winter?
In Winter, Wisconsin, families will find a variety of holiday rentals available, with around 27 options to choose from. The area is known for its stunning natural beauty and outdoor recreational activities, making it an excellent choice for family getaways. Many of these properties feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can enjoy the fresh air.

Visitors can expect amenities such as Wi-Fi for staying connected, as well as access to nearby lakes and trails for hiking and fishing. The locale also offers proximity to attractions like the Chequamegon National Forest, which is ideal for nature walks and wildlife spotting.
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 several pet-friendly house rentals available, providing a welcoming environment for travellers with pets. Many of these properties come equipped with essential amenities such as fully stocked kitchens, outdoor spaces for your pets to enjoy, and comfortable living areas.

The area surrounding Winter is well-suited for pet owners, with nearby parks and trails offering ample opportunities for outdoor activities. Travellers can explore the Chequamegon National Forest, which features a variety of hiking trails and scenic spots great for walking dogs and enjoying nature. Additionally, the area is known for its peaceful lakes, where you can spend time by the water with your furry companions.
Are there any remote work holiday rentals in Winter?
In Winter, Wisconsin, there are numerous remote work holiday rentals available, with around 124 options for those looking to combine work and leisure. Many of these properties are equipped with essential amenities that cater to remote workers, including high-speed Wi-Fi, dedicated workspaces like desks, and some even offer additional features such as computer monitors on request.

The area is surrounded by stunning natural beauty, making it an ideal backdrop for both productivity and relaxation. Travellers can expect comfortable accommodations that often include fully equipped kitchens, allowing for convenient meal preparation. Additionally, many rentals provide spacious living areas and outdoor spaces to unwind after a day of work. 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 rental amenities include kitchens, allowing guests to prepare their own meals, and decks or patios for enjoying the serene surroundings. Many rentals are pet-friendly, accommodating travellers who wish to bring their furry companions along. Onsite parking is also a common feature, making it convenient for those driving to the area. Additionally, most properties come with a coffee and tea maker, ensuring guests have easy access to their morning brews.
When is the best time to visit Winter for a holiday rental?
July is the most popular time to visit Winter, Wisconsin, as families and outdoor enthusiasts flock to the area during the peak summer season. This vibrant period, running from June to August, offers an abundance of activities, including hiking, fishing, and enjoying the picturesque landscapes that the region is known for. The warm weather, with temperatures typically ranging from the mid-teens to low 30s Celsius, provides a great backdrop for exploring the great outdoors.

For those seeking a quieter experience, consider planning your trip in March. While this is part of the low season, it presents a unique opportunity to enjoy the serene beauty of Winter as the area transitions between seasons. You can experience the last remnants of winter while still engaging in activities like cross-country skiing or snowshoeing.

Whichever time you choose to visit, the charm of Winter awaits with its friendly community and stunning natural surroundings.
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.
What are the top attractions in Winter?
In Winter, Wisconsin, visitors can enjoy a range of outdoor activities that highlight the area's natural beauty. One of the main attractions is the Chequamegon National Forest, which offers ample opportunities for hiking, fishing, and wildlife watching. Holiday rentals in nearby communities often provide easy access to the forest's trails and serene lakes.

The area is also known for its excellent snowmobiling and cross-country skiing in the winter months, with trails that cater to various skill levels. Additionally, the nearby Namekagon River is popular for canoeing and kayaking during the warmer seasons, making it a great spot for adventurous visitors.

For those interested in local culture, the nearby town of Hayward features charming shops and restaurants, as well as the National Fresh Water Fishing Hall of Fame. This museum is a unique attraction that showcases the history of fishing in the region and offers a fun experience for families.
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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