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Vacation rentals in Winter

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Vacation rentals for every style

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Popular amenities for Winter vacation rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Stay near Winter's top sights

Winter Co-Op Grocery Store/Hardware Hank3 locals recommend
Lakewood Cafe3 locals recommend
Patti's On 705 locals recommend

Other great vacation rentals in Winter

Top guest favorite
A circular concrete patio surrounds a fire pit, featuring a variety of chairs arranged to encourage gathering. Shadows dance across the surface, and the serene water of the lake is visible in the background, offering a tranquil setting for outdoor activities.
Cabin in Rice Lake
5 out of 5 average rating, 14 reviews

Lakefront Pet-Friendly Cabin on Red Cedar Lake

Guest favorite
Home in Bessemer
5 out of 5 average rating, 9 reviews

Oui Ski Inn: Snowy Summit

Guest favorite
Vacation home in Iron River
4.79 out of 5 average rating, 19 reviews

5 bdrm/Snowmobile trails/hunting/Fishing/Touring

Guest favorite
Chalet in Bessemer
4.96 out of 5 average rating, 112 reviews

Big Chalet with Hot Tub on Big Powderhorn Mountain

Superhost
Cabin in Danbury
4.75 out of 5 average rating, 8 reviews

Great Bear Getaway

Guest favorite
A snow-covered balcony railing is visible in the foreground, while a snow-dusted road extends into the distance. Pine trees are partially obscured by snow, and a glimpse of distant hills is seen under a partly cloudy sky.
Condo in Ironwood Township
4.96 out of 5 average rating, 24 reviews

Cozy home away from home #4 Schnickelfritz

Guest favorite
Home in Ironwood
4.93 out of 5 average rating, 27 reviews

Cheerful 4-bedroom home with a hot tub

Guest favorite
Villa in Bessemer Township
5 out of 5 average rating, 5 reviews

Ultimate Summer Get Away I Alpen Villas at Powderh

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Your guide to Winter

Welcome to Winter

Winter bills itself one of Wisconsin’s largest towns, but it’s referring to the size of the township, not the population — its 900-some residents are scattered across 285 square miles. Winter draws visitors from all over the Midwest because it’s a rustic and gorgeous part of the Northwoods, free of ticky-tacky tourist attractions and vacation traffic. Vast expanses of forest cup the town around its eastern side, and to the northwest is the sprawling Chippewa Flowage. Canoe on the Flambeau River’s whitewaters. Hike through the Chequamegon National Forest. Cross-country ski along the Flambeau Hills Trail. Fish in the Chippewa River or one of the dozen or so lakes that the state keeps stocked with walleye, muskie, bass, and panfish. Your trip to Winter can be as relaxing or exciting as you choose. And isn’t that the reason we take vacations?

The best time to stay in a vacation rental in Winter

The Northwoods region of Wisconsin is known for its comfortable, recreation-friendly summers and its long, snowy winters. Spring comes and goes relatively quickly here, with temperatures settling into the 70s and low 80s Fahrenheit by July, humid but not oppressive. If you’re hiking deep in the woods, you will want breathable long-sleeve shirts and pants, just to protect against bug bites, but bring a swimsuit, too, for all the time you’ll want to spend swimming and boating.

In late September and October, the autumn foliage is so colorful the region experiences another tourism bump — it’s a perfect time to hike, bike, and explore the trails on ATVs. Below-freezing temperatures start in late October, and stick around until April — and the snow cover in December and January gets deep. But that’s the right time to head back into the woods on skis, snowshoes, fat-tire bikes, and snowmobiles, reveling in the magical winter landscapes.

Top things to do in Winter

Tuscobia State Trail

Fans of off-road driving love this corner of the Northwoods for the plethora of well-groomed, scenic ATV trails. And one of Wisconsin’s best is the 62-mile Tuscobia State Trail, which passes through Winter. If you head northeast from town, you’ll hit a spur trail that takes you through the Flambeau River State Forest or, further along, you can link up with the Chequamegon-Nicolet National Forest routes. To the west, you’ll follow the curves and rapids of the Chippewa River before delving into lush woodlands. In winter, snowmobiles take over the trail.

Chippewa Flowage

The damming of the Chippewa River in 1923 created this spectacular, multi-tendriled artificial lake, which has 15,000 acres of water and more than 200 miles of shoreline. Fishing is the main attraction here — anglers particularly love scouting out the moving bogs where walleye, crappie, and muskie hang out — and in the winter, guides help visitors find the right spot on the ice. There are dozens of spots around the lake to slip a canoe or kayak into the water, too. Bring your binoculars for birding — or for getting a closer look at the deer, bears, and otters who make their home here, too.

Chequamegon-Nicolet National Forest

The eastern Chequamegon half of Wisconsin’s largest swath of federally protected land starts about 10 miles north of Winter and stretches out over 865,000 acres of dense maple, oak, pine, and spruce — most of it second-growth forest restored 90 years ago after the area was logged. Here you’ll find hundreds of miles of trails for hiking and cross-country skiing, crystal-clear glacial lakes for swimming and fishing in, streams for navigating in a canoe, and well-groomed routes for exploring on ATV or snowmobile.

Destinations to explore

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