68+ Private Villas and Holiday Rentals in Winter |
  1. USA
  2. Wisconsin
  3. Hayward
  4. Winter

Winter Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Winter

Discover more than 68 vacation rentals available in Winter. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Winter.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Winter, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Winter. On average, places to stay near Winter offer 906.08 ft², with nightly prices averaging US $314.

With Casai, finding and comparing holiday rentals in Winter is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Winter

Type Count
Vacation Homes 21
Cottages 6
Holiday Apartments 2

Use these Quick Filters to Find a Holiday Rental in Winter

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Winter.

Weather in Winter, WI

View the weather forecast for Winter before booking your Winter Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Winter, WI

Casai offers a large selection of top attractions around Winter . Research things to do on your vacation before you visit Winter.


Lake Chippewa
Nelson Lake
Chequamegon National Forest
American Birkebeiner Trail
National Fresh Water Fishing Hall of Fame and Museum
Lac Courte Oreilles
Shues Pond Park
Teal Wing Golf Club
Lost Land Lake
Tremblays Sweet Shop
Hayward Information Center
Hayward Golf Club
Lower Clam Lake
Wilderness Walk Zoo and Recreation Park
Lake Namakagon
Park Theater
Fred Smith's Wisconsin Concrete Park
Park Falls Country Club
Josie Creek County Park
Tiger Cat Flowage

Other Places to Stay in Winter, WI


Sawyer County 482 Properties
Draper 62 Properties
Lake Chippewa 53 Properties

Frequently Asked Questions About Winter?

What are the top holiday rentals in Winter?

With numerous options available in Winter, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Winter:

Which holiday homes in Winter are best for families?

If you're searching for a family-friendly holiday home in Winter, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Winter:

How many Casai.com holiday rentals are available in Winter?

As of 2026, Casai boasts over 68 properties listed in the Winter area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Winter.


People Also Ask

There are 68 Winter, WI Holiday Rentals

Recently Booked Holiday Rentals in Winter