Winter vacation rentals

We found 53 vacation rentals — enter your dates for availability

Discover a selection of 13 homes, 25 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.

Vacation rentals with weekly discounts - Winter

Showing deals for:Nov 7 - Nov 14

Image gallery for Luxury Cabin, 800+ feet frontage, 733 acre Lake, Hot tub, Pontoon, Fireplace .

Property grounds
10 out of 10 rating
Exceptional
(27 reviews)

Luxury Cabin, 800+ feet frontage, 733 acre Lake, Hot tub, Pontoon, Fireplace .

Winter, WI

8% off
Price is $328
$2,299 for 7 nights
All fees included
Luxury Cabin, 800+ feet frontage, 733 acre Lake, Hot tub, Pontoon, Fireplace .

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Find out more about Winter

Find out more about Winter

Why visit Winter

  1. Outdoor Activities: Winter, Wisconsin, is a paradise for outdoor enthusiasts, offering snow tubing, hiking, and more.
  2. Scenic Lakes and Islands: Explore the stunning natural beauty of picturesque lakes and charming islands in the area.
  3. Cozy Accommodations: Choose from cozy cabins and vacation rentals for a comfortable winter retreat.
  4. National Parks: Visit nearby national parks to experience breathtaking landscapes and winter adventures.
  5. Romantic Getaways: Enjoy a perfect setting for couples seeking a romantic escape amidst serene winter beauty.

Popular types of accommodation in Winter

When winter arrives, cozy cabins, houses, and condos become the top choices for travelers seeking the perfect getaway. Whether you’re looking for winter cabin rentals in Wisconsin or a charming retreat to escape the cold, our platform connects you with a variety of options. Embrace the season with the comfort and reassurance of a vacation rental tailored to your needs.

  • Cabins: The top choice for vacationers in Winter, offering a rustic and cozy retreat surrounded by nature.
  • Houses: Ideal for families or groups, these homes provide space and comfort for a memorable stay.
  • Condos: A popular option for those seeking modern amenities and easy access to local attractions.
  • Cottages: Quaint and charming, these small homes offer a peaceful escape in a picturesque setting.
  • Chalets: Rustic yet stylish, chalets provide a unique alpine experience with beautiful views.**

Top attractions in and around Winter

Winter, Wisconsin, is perfect for outdoor enthusiasts and couples seeking a romantic getaway. Explore scenic lakes, charming islands, and nearby national parks. Engage in thrilling winter activities like snow tubing and hiking, or simply enjoy the breathtaking winter landscapes. Whether you're with family or friends, Winter offers a delightful mix of adventure and relaxation, making it an ideal vacation destination.

  1. Lake Chippewa: Experience the romance and stunning scenery of Lake Chippewa, located 6 miles from Winter. Enjoy outdoor activities, relax on the beach, or take in breathtaking sunsets over the water.
  2. Ojibwa State Park: Just 3 miles away, Ojibwa State Park offers adventure and beautiful landscapes. Explore hiking trails, engage in outdoor sports, and immerse yourself in nature’s tranquility.
  3. Winter Town Hall: Situated in Winter, this visitor center is perfect for families. Engage in outdoor adventures and discover local attractions, making it a great starting point for your exploration.

Things to do recommended for families

Your family vacation in Winter, Wisconsin, promises memorable experiences. Enjoy the serene vibes at Doc Smith Park, explore the natural beauty at Chief River State Wildlife Management Area, or unwind at Callahan-Mud Lake State Wildlife Management Area. Each spot offers a perfect blend of relaxation and outdoor fun.

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

When traveling with a group, family, pets, or planning an extended stay, it's important to prioritize your filters effectively. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Winter with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Winter with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Winter: For many families, a vacation wouldn’t feel complete without their furry companion. If you can relate, take a look at Vrbo listings that welcome pets. Most of these pet-friendly accommodations offer amenities like feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Winter: If you're in search of vacation rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Winter

Winter, Wisconsin, offers a cozy retreat perfect for outdoor enthusiasts and romantic getaways. Explore stunning natural scenery and engage in thrilling adventures during the winter months. Whether you're seeking a serene escape or fun entertainment options, this charming city and its surrounding areas provide an ideal backdrop for your vacation. Don't miss the opportunity to experience the magic of a winter getaway in this picturesque location.

  • Ojibwa: Situated a mere 5 miles from Winter, Ojibwa is a charming city that beckons travelers with its stunning natural beauty and outdoor activities. The area is perfect for those seeking a romantic getaway or simply a chance to connect with nature. Visitors can explore recreational areas, enjoy a round of golf at local courses, and take in the picturesque scenery around the town. With nearby landmarks such as pristine lakes and the expansive national state park, Ojibwa offers an ideal backdrop for hiking, picnicking, and taking in the serene surroundings.
  • New Post: A quaint village located 10 miles from Winter, New Post is a hidden gem for outdoor enthusiasts. Known for its breathtaking landscapes and recreational opportunities, this village is perfect for couples and families looking for adventure. Skiing at local resorts is a popular winter activity, while the lakes and water features offer summer fun such as fishing and swimming. With its close-knit community vibe and beautiful scenery, New Post invites visitors to unwind and enjoy the great outdoors.
  • Radisson: Just 11 miles from Winter, Radisson is a lively city that captures the essence of outdoor exploration. Known for its scenic views and romantic atmosphere, Radisson is a haven for those who love golf and recreational activities. Visitors can indulge in a day of golfing at nearby courses, or simply relax by the lakes that dot the landscape. The national state park nearby adds to the allure, providing ample opportunities for hiking and wildlife watching, making Radisson a perfect destination for nature lovers.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 a breeze

Are you interested in cutting costs on your upcoming journey? One way to do this is by being flexible with your travel dates, as prices can vary. Additionally, choosing to book a longer stay often results in significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the best options for your travel needs.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your entire booking. Being the planner truly has its rewards! When you join our travel rewards program, One Key, you'll gain access to exclusive member discounts and earn OneKeyCash™ on eligible bookings. Sign up today and begin enjoying your savings!

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a convenient way to plan your trips, pick up right where you left off, and manage your travel arrangements. You can easily access your previously saved and booked properties, which are organized under Potential, Upcoming, or Current Trips. To explore the features of Trip Boards, simply visit: https://www.vrbo.com/en-ca/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)
  • Lake Chippewa (6.4 mi / 10.4 km)
  • Bluegill Lake (8.8 mi / 14.1 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)

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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.