Winter vacation rentals

We found 52 vacation rentals — enter your dates for availability

Discover a selection of 13 homes, 24 cabins, and other vacation rentals in Winter that are perfect for your trip. Vacation homes offer the amenities you expect for your stay with friends, family, or just your pet, like WiFi and parking. At the end of the day, you're sure to find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Winter

Why visit Winter

  • Scenic outdoor adventures: Enjoy breathtaking landscapes with opportunities for skiing, snowshoeing, and exploring beautiful lakes.
  • Charming cabin retreats: Experience cozy accommodations ideal for romantic getaways and family fun.
  • Picturesque beaches: Relax on serene beaches and soak in the stunning natural beauty of the area.
  • Local attractions: Visit the local visitor center and charming islands for unique experiences.
  • Warm hospitality: Experience the welcoming atmosphere that makes Winter a memorable vacation spot.

Popular types of accommodation in Winter

Planning a winter getaway? Discover the charm of cozy cabins and houses that make for the perfect retreat. From Wisconsin winter cabins to stunning condos, our selection offers something for everyone. Experience the best cabin rentals that promise comfort and adventure, ensuring your stay is filled with warmth and relaxation. Let us help you find the ideal winter haven for your next vacation.

  • Cabins: The top choice for visitors seeking a cozy escape, cabins in Winter offer a rustic ambiance surrounded by nature.
  • Houses: Perfect for families or groups, these spacious homes provide all the comforts of home during your stay.
  • Condos: A great option for those wanting a modern touch, condos offer convenience and amenities in a compact setting.
  • Cottages: These quaint and charming retreats are ideal for a romantic getaway or a peaceful solo retreat.
  • Chalets: With a distinctive alpine style, chalets provide a unique lodging experience amidst stunning surroundings.**

Top attractions in and around Winter

Winter, Wisconsin, is perfect for outdoor and romantic getaways, offering stunning scenery and beach experiences. Visitors can explore beautiful lakes, charming islands, and the local visitor center, making it an ideal destination for those seeking a relaxing and picturesque vacation. Whether you're looking for adventure or tranquility, Winter has a variety of attractions to enhance your stay.

  • Lake Chippewa: Located 6 miles from Winter, Lake Chippewa offers a beautiful beach and picturesque scenery, making it perfect for romantic getaways and outdoor activities. Enjoy a day of swimming, picnicking, or simply soaking in the stunning views.
  • Ojibwa State Park: Just 3 miles away, Ojibwa State Park is a haven for adventure seekers. With its extensive trails and breathtaking landscapes, it’s ideal for hiking, wildlife watching, and immersing yourself in nature.
  • Black Dan Lake: Situated within Winter, Black Dan Lake features a lovely beach atmosphere, perfect for relaxation and romance. Enjoy scenic walks along the shore or engage in water activities amidst serene surroundings.

Things to do recommended for couples

Planning a romantic getaway in Winter, Wisconsin? Enjoy a cozy evening by the campfire under the stars, explore the serene trails for a peaceful hike, or indulge in a couple's massage at a local spa. Don't miss the charming shops and cafes for a delightful afternoon together.

Things to do recommended for families

Your family will love exploring Doc Smith Park, a serene spot perfect for relaxation. A short drive will take you to Callahan-Mud Lake and Chief River State Wildlife Management Areas, both offering beautiful natural settings for outdoor fun and family bonding.

Things to do recommended for groups

Groups visiting Winter, Wisconsin can enjoy a round of golf at Barker Lake Golf Course for a local experience, or take a short drive to Wildwood Marshes Golf Course, located 18 miles away, for more outdoor fun and camaraderie amidst beautiful landscapes.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Winter

If you're traveling with a group, family, pets, or planning an extended stay, be sure to apply the appropriate filters to match your needs. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Winter with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can customize your search for all these options and more on Vrbo.
  • Traveling to Winter with young kids: Traveling with little ones can be quite a task. It's important to prioritize their comfort and safety, along with having suitable amenities like a private pool. Additionally, keeping in mind the distance to family-friendly attractions can make for a more enjoyable experience.
  • Taking your pets with you to Winter: For many, a family vacation wouldn’t feel complete without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly properties come equipped with food bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Winter: If you're in search of vacation rentals that offer great discounts for stays of a month or more, you've come to the right spot. By utilizing the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to enhance your search.

Where to stay near Winter

Winter, Wisconsin, offers a charming escape for those seeking outdoor adventures and stunning scenery. Embrace cozy winter getaways in inviting cabins, perfect for romantic retreats or family fun. Explore nearby natural wonders for unforgettable experiences, whether you're skiing, snowshoeing, or simply enjoying the breathtaking views. With its picturesque landscapes and warm hospitality, Winter is an ideal destination for a memorable winter vacation.

  • Ojibwa: Located 5 miles from Winter, Ojibwa is a charming city that invites travelers to explore its stunning outdoor scenery. Known for its romantic ambiance, Ojibwa offers an array of recreational activities, including golf at local courses, making it an ideal destination for both relaxation and adventure. Visitors can enjoy the beautiful landscapes surrounding the nearby lakes and the enchanting national state park, which provide ample opportunities for hiking and wildlife observation. The town's welcoming neighborhood vibe ensures a delightful experience for all who visit.
  • New Post: Situated 10 miles from Winter, New Post is a picturesque village that is perfect for outdoor enthusiasts and those seeking a serene escape. Known for its scenic beauty, this village offers numerous recreational activities, including skiing and exploring its delightful outdoor areas. The breathtaking lakes and charming water features nearby serve as the perfect backdrop for romantic outings or peaceful reflections. Whether you're hiking or simply enjoying the natural surroundings, New Post promises a refreshing experience with a small-town feel.
  • Radisson: Just 11 miles from Winter, Radisson is another lovely city that captures the essence of outdoor beauty and adventure. With its scenic landscapes and recreational areas, Radisson is a favored spot for golf enthusiasts, boasting well-maintained golf courses. The nearby lakes and national state park provide stunning views and opportunities for exploration, making it an ideal destination for nature lovers. The town's inviting neighborhoods offer visitors a warm welcome, ensuring a memorable experience filled with charm and tranquility.

Best time to go to Winter

If you're planning a trip to Winter, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like February to March and October tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January12.0°F (-11.1°C)No Rain (Dry)Very CloudyAverageAverage
February14.2°F (-9.9°C)No Rain (Dry)Very CloudySlightly LowSlightly High
March28.4°F (-2.0°C)Light RainMostly CloudySlightly LowSlightly Low
April39.2°F (4.0°C)Light RainMostly CloudyAverageSlightly Low
May54.1°F (12.3°C)Light RainMostly SunnyAverageAverage
June64.0°F (17.8°C)Light RainMostly SunnySlightly HighAverage
July68.5°F (20.3°C)Light RainMostly SunnySlightly HighSlightly High
August66.4°F (19.1°C)Light RainMostly SunnySlightly HighSlightly High
September59.0°F (15.0°C)Light RainMostly SunnyAverageAverage
October45.0°F (7.2°C)Light RainMostly CloudySlightly LowAverage
November31.3°F (-0.4°C)Light RainMostly CloudyAverageSlightly Low
December18.7°F (-7.4°C)Light RainMostly CloudyAverageAverage

Booking with Vrbo is simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Also, extending your stay can lead to significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Unlock savings with One Key

When you reserve an eligible Vrbo for your group getaway, you'll receive OneKeyCash on the full booking amount. Being the organizer truly has its benefits. Join our One Key rewards program to unlock exclusive savings for members and earn OneKeyCash on qualifying stays. Sign up today and begin reaping the rewards.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly platform where you can easily create new trips, continue from where you last left off, or manage your travel plans. You'll discover your saved or booked properties neatly organized under categories such as Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Find the perfect vacation rental for your Winter getaway

Experience the unique character of Winter with a stay in a vacation home rental. This city has something for everyone. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Winter

Are you hoping to discover attractions to visit during your stay? Venture out of your cozy vacation rental and experience everything that makes Winter a fun spot to vacation. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • The Tee-Away Golf Course and Supper Club (23.9 mi / 38.4 km)
  • Barker Lake Golf Course (6.8 mi / 10.9 km)
  • Park Falls Country Club (29.4 mi / 47.3 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 looking for exciting outdoor activities or just want to appreciate the scenery, Winter is a great place to spend some time outside. Here are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Lake Winter (1.2 mi / 2 km)
  • Perch Lake (6.3 mi / 10.1 km)
  • Lake Chippewa (6.4 mi / 10.4 km)
  • Campers Island (8.5 mi / 13.6 km)
  • Callahan Lake (16.1 mi / 25.9 km)
  • Teal Lake (18.9 mi / 30.4 km)

Frequently asked questions

How much does it cost to rent a vacation home in Winter?
Prices for vacation 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 vacation 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 skiing in Winter, Wisconsin, the best area to consider for rentals is near the Whitecap Mountains Ski Resort, located a short drive from the town. In and around Winter, visitors can find cozy cabins and chalets that cater to ski enthusiasts. Many properties offer rustic charm, with amenities such as fireplaces, fully equipped kitchens, and outdoor spaces for enjoying the serene winter landscape.

Additionally, nearby attractions include the scenic Chequamegon National Forest, where travelers can find trails for cross-country skiing and snowshoeing. Rentals in Winter often feature easy access to these outdoor activities, with some properties providing warm, inviting living areas superb for relaxing after a day on the slopes.
What is the most popular type of vacation rental accomodation in Winter?
In Winter, cabins are the most popular type of vacation rental, with around 24 available throughout the area. These rustic properties are often located in serene wooded settings, providing a cozy atmosphere ideal for relaxing after a day of outdoor activities. Most cabins feature amenities such as fully equipped kitchens, comfortable living spaces, and porches or decks to enjoy the natural surroundings.

Additionally, there are about 13 vacation houses available, which typically offer more space and amenities suitable for families or larger groups. These houses often include multiple bedrooms, private yards, and entertainment areas, making them great for gatherings. There are also several cottages in the area, which provide a quaint and charming alternative for travelers seeking a peaceful getaway.
Are there any family house rentals in Winter?
In Winter, Wisconsin, there are numerous family-friendly vacation rentals available, with around 29 options to choose from. This area is known for its beautiful natural surroundings and outdoor activities, making it a superb spot for families looking to enjoy time together. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and cozy dining spaces for gathering.

Visitors can expect amenities such as game rooms for entertainment, private decks or patios, and sometimes even access to nearby lakes for swimming or fishing. The local area offers a variety of outdoor adventures, including hiking, biking, and winter sports during the colder months. Additionally, families can explore attractions like the nearby Chequamegon National Forest, which provides opportunities for wildlife viewing and scenic walks. See all family-friendly rentals in Winter.
Can I find long-stay vacation rentals in Winter?
A long-stay vacation rental in Winter is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Winter?
In Winter, Wisconsin, travelers will find a variety of pet-friendly house rentals available, with approximately 22 options to choose from. Many of these rentals are located near natural attractions such as the Chequamegon National Forest, offering a serene setting for those looking to enjoy outdoor activities with their pets. Expect amenities like spacious living areas, fully equipped kitchens, and outdoor spaces where pets can roam freely. Some properties may also feature fire pits and decks, ideal for relaxing after a day of exploring the scenic surroundings. See all pet-friendly rentals in Winter.
Are there any remote work vacation rentals in Winter?
In Winter, Wisconsin, there are a variety of remote work vacation rentals available, with about 32 options to choose from. This area is known for its beautiful natural surroundings, making it an ideal getaway for those who need to balance work and leisure. Many of these properties come equipped with essential remote work amenities such as Wi-Fi, dedicated computer stations, desks, and comfortable chairs, ensuring a productive environment.

Travelers can expect cozy accommodations that often include modern kitchens, spacious living areas, and outdoor spaces superb for taking breaks amidst the scenic beauty of the Northwoods. The nearby Chequamegon National Forest offers numerous recreational opportunities, including hiking and fishing, making it easy 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 vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Winter with parking available—perfect for families or travelers 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, travelers can expect a variety of popular vacation rental amenities that enhance their stay. Most rentals feature fully equipped kitchens, allowing guests to prepare their own meals and enjoy home-cooked dining experiences. WiFi is commonly available, ensuring connectivity for work or leisure. Many properties also include coffee and tea makers, great for starting the day with a warm beverage. Outdoor spaces such as patios are frequent, providing a lovely spot to relax and enjoy the natural surroundings. Additionally, some rentals may offer blenders, ideal for making smoothies or other drinks.
When is the best time to visit Winter for a vacation rental?
The best time to visit Winter for a vacation rental is during the summer months, particularly from June to August. This peak season attracts travelers looking to embrace the great outdoors, with opportunities for hiking, fishing, and exploring the beautiful surrounding landscapes. The warm temperatures, typically ranging from the mid-60s to low 80s Fahrenheit, create ideal conditions for a variety of outdoor activities, allowing visitors to fully enjoy the natural beauty of the area.

July stands out as the most popular month, as it brings a vibrant atmosphere filled with outdoor events and activities. Families and adventure enthusiasts flock to Winter to partake in everything from canoeing on the nearby lakes to enjoying the local festivals that celebrate the region's culture and community spirit. The long daylight hours mean ample time for sightseeing and making the most of your vacation.

If you're looking for a more budget-friendly experience, consider planning your visit in March. During this month, you can take advantage of off-peak rates while still enjoying the tranquility of Winter.
How early should I book a Winter vacation rental?
Book your Winter vacation 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 vacation 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 variety of attractions that highlight the natural beauty of the area. The Chequamegon National Forest offers numerous outdoor activities, including hiking, biking, and wildlife viewing, making it an ideal spot for nature enthusiasts. Vacation rentals in nearby neighborhoods often provide easy access to the forest trails and lakes.

The area is also known for its excellent fishing opportunities, particularly on the nearby Flambeau River, where anglers can find a tranquil setting and a chance to catch various species. In winter, the region transforms into a paradise for snow sports, with opportunities for snowmobiling and cross-country skiing.

Additionally, the local community hosts seasonal events and festivals that celebrate the culture and traditions of Northern Wisconsin, providing a great experience for visitors.
Can I change or cancel my Winter home rental booking on Vrbo?
To find Winter vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, 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 organizing 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.

More Vacation Ideas