Winter vacation rentals

We found 53 vacation rentals — enter your dates for availability

Escape to the enchanting landscapes of Wisconsin, where breathtaking national parks, serene lakes, and charming neighborhoods await your discovery. Whether you’re hiking through Ojibwa State Park’s stunning trails or unwinding by the tranquil shores of Lake Chippewa, adventure beckons at every turn. Perfect for group travelers, our cozy cabins and modern condos provide the comfort and convenience of home, ensuring a memorable retreat filled with nature’s beauty and shared experiences.

Find the best place to stay - Winter

Property grounds
Premier Host
10
Exceptional
48 reviews
Luxury Cabin, 800+ feet frontage, 733 acre Lake, Hot tub, Pontoon, Fireplace .
Winter Vacation Rental | 7BR | 4BA | 6,700 Sq Ft | Stairs Required
Premier Host
9.4
Exceptional
37 reviews
Spacious Winter Retreat w/ River Access + Kayaks!
Firewood available. Lighter on top of refrigerator in the garage.
Premier Host
9.8
Exceptional
72 reviews
5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.
Outdoor dining
Premier Host
9.4
Exceptional
13 reviews
Private, Pet Friendly Lakefront Cabin
Property grounds
10
Exceptional
9 reviews
Pfaff Winter Retreat on Lake Winter. Minutes from Tuscobia trail.
Living area
10
Exceptional
2 reviews
Haven Island on Lake Winter

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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.

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 Chippewa (11.6 mi / 18.7 km)
  • Moose Lake (14 mi / 22.5 km)
  • Callahan Lake (16.1 mi / 25.9 km)
  • Tiger Cat Flowage (18.7 mi / 30 km)
  • Teal Lake (18.9 mi / 30.4 km)
  • Round Lake (19.9 mi / 32.1 km)

Frequently asked questions

What are the best areas to stay in a vacation rental in Winter?
Vacation rentals in Winter offer a variety of options across the city, providing space, privacy, and room to settle in comfortably. You'll find over 40 vacation rentals in Winter, with a strong focus on cabins and houses. For those planning a trip with a large group, over 25 vacation rentals in Winter are well-suited, often featuring multiple bedrooms and spacious living areas. If you're looking for value, over 30 budget-friendly vacation rentals are available, primarily cabins, which offer a cozy stay without compromising on comfort.
What are the most popular vacation rentals in Winter?
The most popular vacation rentals in Winter are cabins, with over 25 available, followed by houses. Guests often choose these property types for their whole-home privacy and ample space, making them ideal for families and groups seeking a comfortable retreat. Cabins provide a rustic charm, while houses offer a more traditional residential experience, both allowing guests to fully immerse themselves in the local environment.
What amenities do vacation rentals in Winter usually offer?
Vacation rentals in Winter typically offer a range of amenities designed for a comfortable stay. You'll often find fully equipped kitchens, internet access, and climate control to ensure a pleasant environment. Many properties also include outdoor areas for relaxation, parking for convenience, and entertainment options like TVs. For those seeking extra comfort, some vacation rentals in Winter feature pools or spa facilities, and several offer winter sport amenities for seasonal activities.
Are there family-friendly vacation rentals in Winter?
Yes, Winter offers over 30 family-friendly vacation rentals, with cabins and houses being the most common property types. These rentals provide the space and privacy families need to relax and enjoy their trip together. Many family-friendly vacation rentals in Winter come equipped with amenities such as games, kayaks for lake activities, and fully equipped kitchens, making meal preparation easy. You might also find properties with firepits for evening gatherings and laundry facilities for longer stays.
Are there pet-friendly vacation rentals in Winter?
Yes, you'll find over 20 pet-friendly vacation rentals in Winter, primarily consisting of cabins and houses. These properties welcome your furry companions, ensuring the whole family can enjoy the trip. Pet-friendly vacation rentals in Winter often feature amenities that cater to pets, such as designated pet areas and clear guidelines for a comfortable stay for everyone. Many properties also permit service animals.
What are the best areas for group vacation rentals in Winter?
Vacation rentals in Winter are well-suited for groups, with over 25 properties designed to accommodate larger parties. Cabins and houses are the most common types of group-friendly rentals, offering ample space and multiple bedrooms for everyone to spread out. These vacation rentals in Winter often include amenities like large dining areas, fully equipped kitchens for shared meals, and plenty of parking, ensuring a comfortable and convenient stay for your entire group.
What are the best luxury vacation rentals in Winter?
For a premium experience, you'll find a selection of luxury vacation rentals in Winter, predominantly houses. These properties offer enhanced comfort and amenities for an indulgent stay. Luxury vacation rentals in Winter often feature amenities such as spa facilities, fireplaces for cozy evenings, and jetted bathtubs, providing a relaxing retreat. These homes are designed to offer a high level of privacy and comfort, perfect for a special getaway.
Are there any budget-friendly vacation rentals in Winter?
Yes, Winter offers over 30 budget-friendly vacation rentals, with cabins being the most prevalent property type for those seeking great value. These rentals provide a comfortable and affordable way to experience the area, often featuring essential amenities that help keep costs down. Budget-friendly vacation rentals in Winter typically include fully equipped kitchens, allowing you to prepare your own meals, and parking, which adds to the overall savings. Choosing a cabin can offer more space for your money, especially when traveling with family or friends.
Are there any vacation rentals in Winter with a hot tub?
Yes, you can find several vacation rentals in Winter that feature a hot tub, primarily cabins and houses. These properties offer a relaxing amenity, perfect for unwinding after a day of exploring. Vacation rentals in Winter with a hot tub often also include other comforting features like fireplaces or firepits, creating a cozy atmosphere for your stay.
Are there any short-term vacation rentals in Winter for a weekend getaway?
Yes, Winter has over 40 vacation rentals available for short-term stays, making it easy to plan a weekend getaway. Cabins and houses are popular choices for shorter trips, offering the convenience of a full home with privacy and space. These vacation rentals in Winter are perfect for a quick escape, providing a comfortable base to explore the area before returning to your private retreat.
Are there any remote work vacation rentals in Winter?
Yes, Winter offers over 30 vacation rentals suitable for remote work or extended stays. These properties, often cabins and houses, provide the necessary amenities to maintain productivity while enjoying a change of scenery. Remote work vacation rentals in Winter typically come with reliable internet access, fully equipped kitchens for convenience, and laundry facilities, allowing for a comfortable and seamless long-term stay.
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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