Discover a selection of 118 vacation rentals in Winter that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including WiFi and air conditioning. Prices start at $130 per night, and cabins and bungalows are popular options for a stay in Winter. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Winter
Destination guide

Winter's coming

It may be small and it may be a day's drive from the nearest city, but Wisconsin's Winter is at the heart of something huge—the great outdoors. With woods that run from horizon to horizon, lakes that glint pristine in the sun, and rivers that split and meander in endless play, Winter is an adventurer's dream. Canoeists delight in the watery possibilities, cross-country skiers lose themselves in the snowy wonder, and families breathe in the pine-scented air. Winter vacation rentals are just the ticket—no matter what the season.

Things to do

Winter's path—from trails to rivers

Winter lies at the heart of the famed Tuscobia State Trail, an old railroad route that's plied by adventurers of every persuasion. It's well-tracked throughout the seasons, but especially when the snows arrive. Many visitors will time the booking of their Winter vacation rentals to coincide with the Tuscobia Winter Ultra—a wintry run-bike-and-ski event. The Flambeau River State Forest is another sight worth days of your time, even if you're not a canoeist. Then there's the 70-foot high-Morgan Falls in the heart of the Chequamegon-Nicolet Forest Park. It commands beautiful views over the Chequamegon Bay of Lake Superior.


Canoers' Winter paradise

Surrounded on all sides by vast expanses of wild landscapes, there is very little you can’t do here in Winter. Highlights include canoeing and kayaking on the waters found rippling all across the landscape (especially the Flambeau River) and the hundreds of miles of tracks open to ATVs, snowmobiles, and mountain bikers alike. Families booking Winter vacation rentals can enjoy camping by tranquil lakes or taking strolls through the delightful woods. And the nearby towns offer up arts and craft festivals that are sure to satisfy the curious.


A Winter for all seasons

Winter by name, winter by nature. Temperatures in this northern Wisconsin town can stay below freezing from November through March. Not that you'll be cozying up in your Winter cabin; it's the time to snap on the cross-country skis or snowshoes and to go and explore. Spring may be brief here, but it comes with an explosion of color on the prairies and in the woodland clearings. But summer is when Winter's wilds become a delight to all— temperatures lift to the mid-70s from June through August. The trails are finally snow-free, while the lakes and rivers are ready for paddling.

Natural features

A wild Winter

The horizon may seem to stretch without a break around your Winter vacation rentals. But there's an incredible diversity to the landscapes here. Once you're out of the surrounding farmland, you'll discover the pine thickets of the Flambeau River State Forest. The Flambeau River itself meanders to the south, while north is the lake country of New Post. Wildlife comes as part of the scenery here; so, expect to see plenty of deer, coyotes, and chipmunks. Bears and wolves are more reclusive, but perhaps the star (if you stay in the forest at night) is the nocturnal flying squirrel.

How many vacation rentals are available around Winter?

Our 2021 property listings offer a large selection of 118 vacation rentals around Winter. From 72 cabin rentals to 72 bungalow rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.