Discover Your Perfect Winter Vacation Homes

Winter Pet Friendly Vacation Rentals

9.8 (14 Reviews)
Cabin
Cozy cabin on Island Lake
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
9.8 (7 Reviews)
Cabin
Private, Pet Friendly Lakefront Cabin
  • Pet Friendly
  • Bedding/Linens
  • Wellness Facilities
View Availability
See More Pet-Friendly Vacation Rentals in Winter on PetFriendly.io

Why Choose Rent By Owner for your Winter Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Winter

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here can enhance your experience, whether you're seeking winter scenery or seasonal activities in this charming region of Wisconsin.

Peak Season Highlights

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Winter (December to February)

This destination experiences its peak during the winter months when snow sports and holiday festivities attract many visitors eager to enjoy the region's winter wonderland.

Average Temperature Daytime: 20°F to 30°F - Nighttime: 5°F to 15°F
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Late Fall (November)

The early winter season also sees increased activity as travelers visit for seasonal events and to prepare for the snowy months ahead, making it an ideal time to secure cozy vacation rentals in the area.

Average Temperature Daytime: 40°F to 50°F - Nighttime: 25°F to 35°F

Off-Season Highlights

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Spring (March to May)

As the snow melts and temperatures rise, this destination transitions into a quieter period perfect for enjoying the area’s natural beauty without the crowds.

Average Temperature Daytime: 45°F to 65°F - Nighttime: 25°F to 45°F
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Summer (June to August)

During the warm summer months, fewer visitors come, offering a serene escape where you can explore the region's outdoor scenery at your own pace with comfortable weather conditions.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F

Weekly Weather Forecast for Winter

How to Book Your Winter Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Winter

More Top-Rated Vacation Rentals in Winter Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor seating areas such as patios or decks to relax and take in the scenic surroundings.
  • Take advantage of private fire pits for cozy evenings under the stars.
  • Benefit from well-maintained hiking or nature trails nearby, perfect for exploring this region's natural beauty.
  • Utilize spacious yards or gardens for outdoor activities with family and friends.
  • Make use of outdoor grills and barbecue stations to prepare meals while enjoying the fresh air.
  • Access to outdoor sports amenities like volleyball courts or horseshoe pits commonly found here.
  • Experience outdoor water features or hot tubs that enhance your relaxation amidst the region’s natural setting.

Top Attractions Around Winter

What attractions are nearby?

During your stay here, you'll find a variety of winter activities nearby, including snowshoeing, cross-country skiing, and scenic nature trails to explore in this charming destination.

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Family Activities

  • Winter Sports at Nordic Mountain: Experience thrilling downhill skiing and snowboarding right in the area, perfect for family members of all ages seeking winter adventure.
  • Snowshoeing and Cross-Country Skiing: Explore scenic trails that weave through the region’s snow-covered landscape, offering a peaceful way to enjoy the winter outdoors with your loved ones.
  • Winter Festival Events: Participate in local seasonal celebrations that feature festive activities, crafts, and entertainment suitable for the entire family to enjoy together.
  • Ice Skating at Local Rinks: Enjoy family-friendly ice skating at nearby rinks, providing fun and active entertainment during your stay in this winter destination.
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Adult Activities

  • Skiing and Snowboarding: Enjoy the world-class slopes in this winter haven, perfect for adrenaline-filled days on your vacation rental's doorstep.
  • Snowshoeing and Cross-Country Skiing: Explore scenic trails around the area that offer peaceful winter adventures right from your rental property.
  • Ice Skating: Experience outdoor ice skating at popular local rinks or frozen lakes, ideal for a fun-filled winter activity during your stay.
  • Winter Wildlife Viewing: Discover the region’s winter wildlife by visiting nearby parks and nature reserves, providing a serene escape for nature enthusiasts staying in this destination.

Other Places to Stay in Winter, WI

Sawyer County
Sawyer County Vacation Rentals
Draper
Draper Vacation Rentals
Lake Chippewa
Lake Chippewa Vacation Rentals
More Places to Stay Near Winter

Winter Travel Tips

How Can You Make the Most of Your Stay?

  • Embrace Local Winter Activities: Take advantage of the area’s popular winter sports, such as cross-country skiing and snowshoeing, available near your vacation rental to fully enjoy the season.
  • Plan Ahead for Weather Conditions: Keep an eye on local weather reports to ensure your outdoor plans are safe and enjoyable during your stay in this winter destination.
  • Choose a Cozy Accommodation: Select a well-equipped vacation rental with heating and warm amenities to make your winter experience comfortable and memorable.
  • Explore Nearby Scenic Spots: Use your stay as an opportunity to discover scenic winter landscapes and peaceful areas that showcase the region’s natural beauty in the colder months.

Transportation Options

  • Personal Vehicles: Driving your own car provides the freedom and convenience to explore the area at your own pace while staying close to your vacation rental.
  • Rental Cars: Renting a vehicle is an excellent option for easy access to nearby attractions and for navigating the region comfortably during your stay.
  • Public Transit: Public transportation services offer a cost-effective way to get around here, connecting you to key points of interest without the hassle of parking.
  • Taxi and Ride-Sharing Services: Taxis and ride-sharing options like Uber or Lyft provide quick, reliable transportation directly to your vacation rental or local destinations in this destination.

Local Customs Options

  • Winter Wisconsinites' Winter Rituals: Participating in local snowshoeing and cross-country skiing traditions is a common way to embrace the area's snowy landscape during your stay.
  • Frosty Festivities: Community celebrations often feature hearty, traditional foods like warm soups and seasonal baked goods, reflecting the region’s cozy winter hospitality.
  • Respect for Nature's Cycles: It’s customary here to observe and respect the local wildlife and natural surroundings, especially during the freezing months when the landscape transforms.
  • Holiday and Winter Celebrations: You’ll find that local customs include participating in festive holiday events and winter fairs that bring residents and visitors together to celebrate the season.

Frequently Asked Questions About Winter?

1. What are the top vacation rentals in Winter?

There are a lot of options in Winter. If you plan on staying in the Winter area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Winter:

2. Which vacation homes in Winter are best for families?

If you are looking for a family-friendly vacation home in Winter, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Winter:

3. How many Rentbyowner vacation rentals are available in Winter?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 68 in the Winter area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Winter. 

4. What is the cancellation policy for vacation rentals in Winter, Wisconsin?

The cancellation policy varies depending on the property owner and listing details. It’s important to review the specific policies listed on the property page or contact the owner directly to understand the terms before booking.

5. Are there any additional fees I should be aware of when booking a vacation rental here?

Additional fees such as cleaning fees, service charges, or local taxes may apply. These details are typically outlined in the listing, so it’s advisable to read through the full fee breakdown or reach out to the owner for clarification.

6. How do I ensure my reservation is secure when booking in this area?

Book through trusted platforms that offer secure payment options. Always verify the listing details and communicate with the owner through verified channels to ensure your reservation is legitimate and protected.

7. What amenities are typically available in vacation rentals in Winter, Wisconsin?

Amenities can vary widely but often include essentials like Wi-Fi, kitchen facilities, heating, and parking. For specific amenities, check the individual listing or contact the property owner directly.

8. How far in advance should I book to guarantee availability during peak seasons?

To secure the best options during busy times, it’s recommended to book several months ahead. Availability can fill quickly, especially for popular dates or properties in this destination, so early planning is advised.