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Winter winter cabin rentals

Book unique cabins, vacation rentals, and more on Airbnb

Top-rated cabin rentals in Winter

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

Cabin in Ladysmith
Flaming Torch Lodge
This is a quaint little cabin on the Flambeau River just outside of Ladysmith, WI (flambeau translastes to flaming torch) It is clean and newly remodeled. It has a fully equipped kitchen, stove and fridge. A gas fireplace is the centerpiece of the living room space. Snuggle up on the leather sofa or recliner, turn on the fireplace, grab a good book, hot chocolate and relax. There is one bedroom with a memory foam mattress. A loft with a sleeper couch. No pets and no smoking at any time please.
$132 per night
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Cabin in Winter
Paradise Pines
Quiet, cozy north woods cabin located about 45 minutes southeast of Hayward, WI. Perfect place to escape the grind of everyday life! Fishing, hiking, ATV/snowmobile trails accessible within a mile of the cabin, cross country skiing, golf, and hunting close by. Property borders thousands of acres of public hunting land. Hayward area amenities also include mini golf, many small shops and candy/ice cream, and freshwater fishing hall of fame. Please note: pets are not allowed inside.
$99 per night
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Cabin in Ojibwa
Available Christmas! Secluded Riverview Cabin
This secluded cabin is perfect for a Christmas getaway with family. A full coffee bar, cozy two-sided fireplace, fast WIFI for streaming Christmas movies, and panoramic windows make for great family memories in a winter wonderland. Sleds included-the driveway makes for a great snow hill! Just 3/4 miles away from the Tuscobia Trail for snowmobile enthusiasts. Christmas dates will go fast, so book today.
$102 per night

Winter cabin rentals

Cabin in Hayward
Osprey Cabin
$83 per night
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Cabin in Hayward
Private Home on Upper Twin Lake, Close to Trails
$113 per night
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Cabin in Hayward
Hayward Four Season Moose Lake Getaway
$148 per night
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Cabin in Hayward
Your Northwoods Escape!
$157 per night
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Cabin in Hayward
Aspen Cabin-Lost Land Lake Waterfront Getaway
$153 per night
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Cabin in Winter
Hemlock Haven Resort 1
$165 per night
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Cabin in Hayward
Cabin 5 on beautiful Round Lake Grand Pines Resort
$149 per night
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Cabin in Hayward
Charming Cabin right on Round Lk in Richardson Bay
$198 per night
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Cabin in Hayward
Vintage 1940's Hayward Cabin!
$162 per night
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Private room in Hayward
Hayward, WI Chippewa Flowage Cozy Studio Apt Cabin
$76 per night
Cabin in Exeland
Lakeside Northwoods Retreat
$132 per night
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Cabin in Winter
Waterfront cabin on Connor’s Lake. Sleeps 6
$147 per night
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Christmas cabin rentals in Winter

Cabin in Winter
Connors Lake Cabin
$400 per night
Cabin in Hayward
Osprey Hideaway; So Cozy and Close to Trails!
$214 per night
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Cabin in Hayward
Lovely Private Lakefront Retreat, Near Hayward
$164 per night
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Cabin in Hayward
Private Hayward Lodge, 3 Docks on 8 Forested Acres
$385 per night
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Cabin in Hayward
Country Cabin on the Chippewa Flowage, Hayward WI
$129 per night
Cabin in Hayward
The Pines Cabin at Timber Bay on Spider Lake!
$139 per night
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Cabin in Hayward
Cabin #5 on the Chippewa Flowage
$91 per night
Cabin in Weirgor
Cozy Cabin on 10 Acres, Walk to Chippewa River!
$147 per night
Cabin in Hayward
Muskie Ridge
$249 per night
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Cabin in Ladysmith
The Whitetail Cabin
$211 per night
Cabin in Hayward
NEW LISTING! Cozy Rustic Northwds Cabin-Round Lake
$201 per night
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Cabin in Hayward
Cozy Cabin on Beautiful Grindstone Lake
$121 per night
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Winter winter cottage rentals

Cottage in Tony
Luxe Lakeshore Cottage Retreat | Dock | Firepit
$222 per night
Cottage in Tony
Beautiful cottage on Lake Flambeau
$126 per night
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Cottage in Couderay
Chippewa Flowage cottage
$285 per night
Cottage in Hayward
Whispering Pines Hideaway located on Lake Gurno
$200 per night
Cottage in Hayward
Gritzy's Round Lake Retreat
$160 per night
Cottage in Hayward
NEW! Cozy Hayward Cottage w/ Dock & Lakefront View
$176 per night
Cottage in Hayward
Available Thanksgiving! Lake cottage w/King Suite
$94 per night
Cottage in Couderay
Cozy Cottage on Blueberry Lake
$220 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?


When is 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 cozy up in one of the area’s cabins for rent and to head back into the woods on skis, snowshoes, fat-tire bikes, and snowmobiles, reveling in the magical winter landscapes.


What are the 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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