Winter vacation rentals

We found 51 vacation rentals — enter your dates for availability

Discover a selection of 12 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.

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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)
  • 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 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)
  • Barker Lake (6.4 mi / 10.3 km)
  • Lake Chippewa (6.4 mi / 10.4 km)
  • Black Dan Lake (6.6 mi / 10.6 km)
  • Callahan Lake (16.1 mi / 25.9 km)
  • Tiger Cat Flowage (18.7 mi / 30 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 ski resort rentals in Winter, Wisconsin, travelers should focus on the area surrounding the Flambeau River State Forest and the nearby Park Falls area, which is home to several winter sports opportunities. The closest ski areas are located in the nearby towns, where visitors can find cozy cabins and lodges that cater specifically to winter sports enthusiasts.

Many of these properties offer amenities such as warm, inviting living spaces with fireplaces, fully equipped kitchens for self-catering, and access to outdoor recreational activities right outside their doors. Some rentals may have hot tubs, providing a relaxing way to unwind after a day on the slopes. Additionally, travelers can expect options with proximity to snowmobile trails and cross-country skiing routes, making it easy to explore the winter landscape.

In Winter itself, guests can discover charming cabins that blend rustic charm with modern comforts, often featuring convenient amenities like Wi-Fi and laundry facilities. The community is also close to local shops and dining options, enhancing the overall experience for visitors who want to enjoy both outdoor activities and cozy downtime.
What is the most popular type of vacation rental accomodation in Winter?
In Winter, Wisconsin, cabins are the most popular type of vacation rental, with about 24 available in the area. These cabins are often located in serene natural settings, providing a rustic charm that appeals to travelers looking for a peaceful getaway. Most feature amenities such as fully equipped kitchens, cozy living areas with fireplaces, and outdoor decks or fire pits for enjoying the tranquil surroundings.

In addition to cabins, there are around 10 vacation houses available, which cater to families or larger groups seeking more space and comfort. These houses typically offer multiple bedrooms and living areas, allowing guests to relax and gather together. There are also several cottages scattered throughout Winter, adding to the diverse range of accommodations.
Are there any family house rentals in Winter?
In Winter, Wisconsin, there are numerous family-friendly house rentals available—about 27 options to choose from. This area is surrounded by beautiful forests and lakes, making it an excellent spot for outdoor enthusiasts. Many of these homes offer spacious living areas, fully equipped kitchens, and outdoor spaces superb for family gatherings or barbecues.

Visitors can expect amenities such as cozy fireplaces, game rooms for entertainment, and sometimes even access to private docks or nearby swimming spots. The locale is close to attractions like the Chequamegon National Forest, where families can explore hiking trails, go fishing, or enjoy winter sports during the colder months.
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 can find a variety of pet-friendly house rentals, with around 25 options available to choose from. The area is known for its beautiful natural surroundings, making it a great destination for those looking to enjoy outdoor activities with their pets. Many vacation homes in Winter come equipped with amenities such as spacious yards, decks or patios for relaxation, and fully equipped kitchens for convenient meal preparation.

Additionally, the nearby Chequamegon National Forest offers numerous trails and scenic spots that are great for hiking and exploring with your furry friends. The serene atmosphere of Winter, combined with its pet-friendly accommodations, ensures a delightful experience for both pets and their owners.
Are there any remote work vacation rentals in Winter?
In Winter, Wisconsin, there are numerous options for remote work vacation rentals, with around 31 available in the area. Many properties are equipped with high-speed Wi-Fi, ensuring a reliable connection for work-from-home needs. Travelers can expect a range of amenities, including comfortable workspaces, large living areas, and fully equipped kitchens, making it easy to balance work and leisure during their stay.

The surrounding area offers opportunities for outdoor activities, such as hiking and fishing, allowing for a refreshing break from work. The scenic landscape of Winter provides a peaceful backdrop, enhancing productivity and relaxation alike. 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, popular vacation rental amenities include fully equipped kitchens, allowing guests to prepare their own meals and enjoy dining in the comfort of their rental. Many properties feature decks or patios, providing outdoor spaces to relax and take in the natural surroundings. Additionally, several rentals permit pets, making it easier for travelers to bring their furry companions along. Onsite parking is also commonly available, ensuring convenience for guests with vehicles. Lastly, amenities like coffee and tea makers are often included, suiting those who enjoy a warm beverage to start their day.
When is the best time to visit Winter for a vacation rental?
The peak season for visiting Winter, Wisconsin, spans from June to August, making it the ideal time for families and outdoor enthusiasts eager to enjoy the great outdoors. During these summer months, travelers can partake in a myriad of activities such as fishing, hiking, and boating on the picturesque lakes that surround the area. The warm temperatures, typically ranging from the mid-60s to mid-80s Fahrenheit, create a welcoming environment for exploring the stunning natural beauty of the Northwoods.

July stands out as the most popular month to visit Winter, as it offers the superb blend of warm weather and vibrant community events. This is when you'll find the local festivities in full swing, including outdoor concerts and farmers' markets, bringing a lively option to the region. The long daylight hours provide ample opportunity for sightseeing and outdoor adventures, making it a favorite among travelers seeking a mix of relaxation and excitement.

For those looking for more budget-friendly options, consider planning your trip in March. While temperatures can be cooler, usually hovering in the mid-30s to low 50s Fahrenheit, this month offers a unique charm as the area transitions from winter to spring. You'll find fewer tourists, allowing for a more serene experience while enjoying the early signs of nature's awakening.

Ultimately, whether you're drawn to the bustling summer activities or the peacefulness of early spring, Winter has something to offer every traveler.
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, Wisconsin, United States of America?
In Winter, Wisconsin, visitors can take part in the natural beauty of the area. One of the main attractions is the nearby Chequamegon National Forest, where outdoor enthusiasts can enjoy hiking, biking, and wildlife viewing. The forest offers numerous trails and scenic spots, superb for a day of exploration.

For those interested in water activities, the Namekagon River provides opportunities for fishing, canoeing, and kayaking, making it a popular destination for summer recreation. Additionally, the Winter Sports Area is a great spot for winter activities, including snowmobiling and cross-country skiing, attracting visitors during the colder months.

The town itself features charming local shops and restaurants that reflect the community's character, providing a cozy atmosphere for travelers to enjoy.
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.

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