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Vacation rentals in Winter

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Top-rated vacation rentals in Winter

Guests agree: these stays are highly rated for location, cleanliness, and more.

Cabin in Ladysmith
Flaming Torch Lodge (No Cleaning Fee)
This is a quaint little cabin on the Flambeau River just outside of Ladysmith, WI (flambeau translastes to flaming torch) It is a clean space with rustic charm. It has a fully equipped kitchen, stove and fridge. A gas fireplace is the centerpiece of the living room. Snuggle up on the sofa or recliner, turn on the fireplace, and relax. There is one bedroom with a memory foam mattress. A loft with a sleeper couch. Free amenities, including cleaning. No pets and no smoking at any time please.
ﺩ.ﺇ535 per night
Cabin in Hayward
Hayward Haus, Modern Design w/ Classic Experience
Built as a winter or summer escape for a couple or small group, this beautiful four season cabin is a great way to experience the Northwoods of Wisconsin in a modern, well-appointed, aesthetically rich space designed with relaxation in mind. A heavy emphasis has been placed on style, comfort, usability of space, and privacy. Cabin is brand new as of August 2021. Host is 13 year "superhost" Note: Summer and Fall calendars have restrictions intended to eliminate one night calendar gaps.
ﺩ.ﺇ743 per night
Cabin in Frederic
Nordlys Lodging Co. - MetalLark Tower
Perched high among the trees with breathtaking views of the hidden lake and wildflower meadows, MetalLark Tower is the perfect getaway. This two-story, 800 sq.ft. cabin has one king bed, one hide-away bunk bed, and one bathroom. We put the living area high up on the second floor to give our guests a bird’s eye view. Floor to ceiling glass brings the outdoors inside, and each season brings its own unique perspective. Staying in MetalLark tower is truly a one-of-a-kind experience.
ﺩ.ﺇ1,309 per night

Other great vacation rentals in Winter

Cabin in Winter
Loons Nest Cabin on Private Lake
ﺩ.ﺇ584 per night
Cabin in Hayward
Cozy cabin on the water but close to everything!
ﺩ.ﺇ417 per night
Home in Ladysmith
North Country Cottage
ﺩ.ﺇ341 per night
Apartment in Hayward
Sunset Lake View Apt Callahan Lake
ﺩ.ﺇ441 per night
Home in Winter
Bungalow Trail
ﺩ.ﺇ404 per night
Cabin in Winter
Bobbers Cabin on Private Lake
ﺩ.ﺇ606 per night
Apartment in Winter
Gateway to the Great North Woods by DonBar
ﺩ.ﺇ422 per night
Guesthouse in Ojibwa
ATV/Side by Side enthusiasts! Private rd.
ﺩ.ﺇ290 per night
Cabin in Ojibwa
Secluded Ski-In/Ski-Out Cabin-2 King Beds
ﺩ.ﺇ469 per night
Cabin in Winter
The Hideaway on Highland
ﺩ.ﺇ845 per night
Cabin in Winter
Northwoods Cabin
ﺩ.ﺇ655 per night
Cabin in Hayward
The Seeley Oaks A-Frame
ﺩ.ﺇ569 per night

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.

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