Winter, WI Resort Rentals

Winter Resorts

Resort

"The Loft" @ Moxi Lodge and Lounge

10.0

Exceptional

(16 Reviews)

1 Bath 4 Guests 1500 ft²

US $300/Night 7 Nights - US $2,101

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Resort

"The Birchwood" @ Moxi Lodge and Lounge

10.0

Exceptional

(15 Reviews)

1 Bath 6 Guests 2000 ft²

US $323/Night 7 Nights - US $2,261

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Resort

"The Whitetail" @ Moxi Lodge and Lounge

10.0

Exceptional

(3 Reviews)

1 Bath 6 Guests 2000 ft²

US $352/Night 7 Nights - US $2,462

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Cabin

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

10.0

Exceptional

(40 Reviews)

2 Bedrooms 1 Bath 6 Guests

US $422/Night 7 Nights - US $2,954

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House

The Bear Den

10.0

Exceptional

(1 Review)

1 Bedroom 1 Bath 8 Guests 139.93 ft²

US $110/Night 7 Nights - US $772

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Cabin

EAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River

10.0

Exceptional

(24 Reviews)

1 Bedroom 1 Bath 4 Guests

US $149/Night 7 Nights - US $1,041

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Spacious Winter Retreat w/River Access + Kayaks!

House

Spacious Winter Retreat w/River Access + Kayaks!

7 Bedrooms 5 Baths 18 Guests 6705.92 ft²

US $1,601/Night 7 Nights - US $11,207

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Cabin

Pets & kid Friendly ,direct access to ATV& snow trails, private dock

10.0

Exceptional

(17 Reviews)

2 Bedrooms 1 Bath 5 Guests 400 ft²

US $201/Night 7 Nights - US $1,404

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House

Luck Charlie Lodge home

3 Bedrooms 2 Baths 6 Guests 1313.2 ft²

US $557/Night 7 Nights - US $3,897

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Price Dropped

Cabin

Cozy cabin on Island Lake

10.0

Exceptional

(12 Reviews)

3 Bedrooms 1 Bath 6 Guests 624 ft²

US $203/Night 7 Nights - US $1,422

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Cabin with Golf Course Across the street

House

Cabin with Golf Course Across the street

1 Bedroom 1 Bath 4 Guests 796.53 ft²

US $262/Night 7 Nights - US $1,832

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Cottage

Winter Nights Cottages: Cottage 4 Winter, Wisconsin vacation rental

10.0

Exceptional

(6 Reviews)

1 Bedroom 1 Bath 7 Guests

US $161/Night 7 Nights - US $1,126

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More Top-Rated Resorts in Winter Area

Why Choose Rent By Owner for your Winter Resorts?

What makes our Resorts special?

Verified Listings

Book with confidence knowing every property meets our quality and safety standards.

Unbeatable Value

Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.

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 Resorts stay?

Choosing the optimal time to vacation here can enhance your experience, as seasonal variations in Winter, Wisconsin offer distinct opportunities for relaxation and outdoor activities in the area’s trusted resorts.

Peak Season Highlights

Winter (December to February)

During the peak winter months, you can enjoy ideal conditions for snow sports and cozy indoor activities in this area.

Average Temperature Daytime: 20°F to 30°F - Nighttime: 0°F to 15°F

Early Fall (September to October)

This period offers beautiful foliage and pleasant weather, making it a popular time for outdoor adventures and scenic exploration.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F

Off-Season Highlights

Late Spring (April to May)

In late spring, the region experiences milder weather with fewer visitors, providing a quieter setting for relaxation and exploration.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 30°F to 40°F

Summer (June to August)

The summer months bring warmer temperatures and longer days, perfect for enjoying the natural scenery of this destination.

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

Weekly Weather Forecast for Winter

How to Book Your Winter Resorts

What's our booking process?

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

Booking Steps

Search Properties

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

Select a Rental

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

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 Resorts in Winter Area

Common Resorts Amenities

What amenities can you expect?

Our Resorts 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 a cozy outdoor fireplace to gather around during chilly evenings in this winter destination.
Take advantage of snowshoeing or cross-country skiing trails directly accessible from your resort stay.
Relax on private patios or decks that offer scenic views of the surrounding snowy landscape.
Make use of outdoor hot tubs or spas for a relaxing soak while surrounded by winter scenery.
Benefit from outdoor fire pits perfect for roasting marshmallows and sharing stories under the stars.
Explore nearby nature trails ideal for hiking or snow trekking, right outside your accommodation.
Utilize designated outdoor parking areas designed to accommodate winter conditions easily and safely.

Top Attractions Around Winter

What attractions are nearby?

While staying at this destination, you can enjoy a variety of winter activities nearby, including skiing, snowboarding, and snowshoeing, all set against the picturesque backdrop of Winter, Wisconsin, making it an ideal spot for outdoor enthusiasts seeking a reliable and memorable getaway.

Family Activities

Snowshoeing and Winter Hiking: Explore the scenic trails throughout the region, offering an active way to enjoy the winter landscape with your family.
Skiing and Snowboarding: Experience exhilarating downhill adventures at nearby ski resorts suitable for all skill levels within this charming destination.
Ice Skating: Enjoy classic winter fun on outdoor ice skating rinks that are perfect for families seeking a festive activity in the area.
Wildlife Watching and Nature Tours: Discover local wildlife and enjoy guided nature excursions that highlight the unique winter ecosystem of here.

Adult Activities

Snowshoeing and Cross-Country Skiing: Explore the scenic trails in the region by snowshoeing or cross-country skiing, offering a peaceful way to enjoy winter’s beauty right outside your resort.
Ice Skating: Enjoy glide sessions on local outdoor rinks or frozen lakes, providing a classic winter activity for adults seeking outdoor fun in this area.
Sleigh Rides: Experience the charm of a traditional sleigh ride through snowy landscapes, perfect for a romantic or relaxing outing during your stay here.
Winter Photography Tours: Capture breathtaking winter scenery on guided photography tours that highlight the area's stunning snowy vistas and natural beauty.

Other Places to Stay in Winter, WI

Winter Travel Tips

How Can You Make the Most of Your Stay?

Plan Your Winter Excursions in Advance: Secure your preferred resorts in Winter, Wisconsin early to ensure access to the best amenities and comfortable accommodations during peak season.
Explore Local Winter Activities: Take advantage of the region's seasonal offerings by engaging in activities such as snowshoeing or cross-country skiing right near your resort.
Pack Appropriately for Cold Weather: Bring layered clothing, waterproof gear, and essentials to stay warm and comfortable throughout your stay in this destination.
Utilize On-Site Amenities: Maximize your experience by making full use of the amenities available at your resort, from cozy common areas to recreational facilities designed for winter fun.

Transportation Options

Personal Vehicles: Renting or driving your own car offers the flexibility to explore the area at your own pace, especially useful for visiting nearby outdoor attractions and scenic spots in Winter, Wisconsin.
Shuttle Services: Local shuttle services provide convenient transportation between resorts and key points of interest, ensuring a hassle-free experience during your stay in this region.
Public Transit: Buses operated within the area connect you to various parts of Winter and neighboring communities, offering an economical way to navigate the region.
Taxi and Ride-Sharing: Taxis and ride-sharing options like Uber or Lyft are readily available here, providing quick and reliable transportation for short trips around the destination.

Local Customs Options

Winter Water Lantern Festival: During the winter months, residents and visitors celebrate this beautiful event featuring floating lanterns that symbolize hope and remembrance on local lakes.
Ice Fishing Traditions: Embracing the cold, engaging in ice fishing is a beloved regional custom, where communities gather on frozen surfaces to enjoy this peaceful outdoor activity.
Snowman Building Contests: The region hosts lively snowman building competitions that bring locals together to showcase their creativity amidst the snowy landscape.
Winter Harvest Festivals: Seasonal harvest celebrations highlight regional produce and crafts, fostering community spirit despite the chilly weather.

Winter Resorts Frequently Asked Questions

1. What are the top Resorts 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 Resorts in Winter:

2. How many Resorts are available in Winter?

Currently, the total number of properties listed by RBO in 2026 is over 3 in the Winter area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Resorts in Winter. 

3. What is the cancellation policy for resorts in Winter, Wisconsin?

Cancellation policies vary depending on the specific resort you book. To ensure your plans are flexible, review the policy details on the listing or contact the property owner directly for precise information.

4. Are there any additional fees I should be aware of when booking a resort in this area?

Additional fees such as cleaning charges, resort fees, or security deposits may apply. For a clear understanding of all costs involved, please read the listing details or reach out to the host before finalizing your reservation.

5. What amenities can I expect during my stay at resorts in Winter, Wisconsin?

Amenities differ from one property to another, but common features include cozy fireplaces, outdoor recreational facilities, and modern conveniences. Check the specific listing for a comprehensive list of available amenities during your visit.

6. How do I confirm my reservation at a resort in this destination?

Reservation confirmation typically occurs after booking through the platform, with payment processed directly. For any special requests or confirmation needs, contacting the property owner is recommended.

7. Is there a minimum stay requirement for resorts in this region during winter?

Minimum stay requirements may vary depending on the resort and the time of year. Review the booking details for the specific property or contact the owner to clarify the minimum nights needed for your desired dates.