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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 Ojibwa
NEW! Wildwood Escapes-Chippewa River Cabin
Escape to the tranquility of Chippewa River Cabin and unwind among 10 secluded acres and 300ft of river frontage. Take in stunning views of the river and wildlife through panoramic windows. Enjoy the comfort of central AC and the convenience of nearby Hayward for indoor and outdoor adventures. Hike, bike, or ATV along the Tuscobia Trail just 3/4 mi away. Savor a cup of joe from the full coffee bar or set out on the river w/included kayaks. Experience the perfect getaway and book your stay today!
$135 per night
Cabin in Winter
Hemlock Haven Resort 1
Our small resort is reminiscent of the gems that are largely gone in the Northwoods. A quiet, peaceful cabin on the shore of a sportsmen's lake. Barker Lake is a 240 acre lake set in the National Forest. Wildlife is more plentiful than people. Just 25 min southeast of Hayward gets you to the tourist action if you want it. A 14' rowboat comes with the cabin and motor can be rented. The lake is a class A musky lake with smallmouth and various panfish. Kayaks are available free of charge.
$165 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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Winter cabin rentals

Cabin in Hayward
The Timberjack
$82 per night
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Cabin in Hayward
Private Home on Upper Twin Lake, Close to Trails
$85 per night
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Cabin in Ojibwa
Cabin #3 - Two bedroom cabin on the water
$131 per night
Cabin in Winter
Loons Nest Cabin on Private Lake
$159 per night
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Cabin in Ladysmith
Flaming Torch Lodge
$108 per night
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Cabin in Hayward
"Das Blockhaus" - cozy, authentic German log cabin
$92 per night
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Cabin in Hayward
Honey Bear Hideaway-cabin in the heart of Hayward
$82 per night
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Cabin in Hayward
Cozy Cabin on Secluded Peninsula
$98 per night
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Cabin in Winter
Waterfront cabin on Connor’s Lake. Sleeps 6
$154 per night
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Cabin in Cable
Hygge House
$130 per night
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Cabin in Hayward
Lilypad Lake House - Nelson Lake
$200 per night
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Cabin in Birchwood
Lakefront Sunset Cabin w/Boats, Spa, FirePit & BBQ
$173 per night
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Christmas cabin rentals in Winter

Cabin in Hayward
Cozy cabin on the water but close to everything!
$117 per night
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Cabin in Hayward
Cabin #5 on the Chippewa Flowage
$91 per night
Cabin in Hayward
Cabin #2, Musky Joe's Resort, Hayward, WI
$76 per night
Cabin in Hayward
Vintage 1940's Hayward Cabin!
$159 per night
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Cabin in Hayward
Rustic Charming Cabin. Updated Pontoon!
$143 per night
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Cabin in Cable
Bright 2 bedroom on beautiful Lake Owen
$101 per night
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Cabin in Hayward
Lakeshore Lily Pad
$79 per night
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Cabin in Stone Lake
Slice of Paradise on Slim Lake
$135 per night
Cabin in Hayward
Aspen Cabin-Lost Land Lake Waterfront Getaway
$154 per night
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Cabin in Hayward
Cabin #3, Musky Joe's Resort, Hayward, WI
$105 per night
Cabin in Hayward
Charming Cabin right on Round Lk in Richardson Bay
$189 per night
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Cabin in Birchwood
Birch Lake Bungalows, Birchwood, WI (Bear's Den)
$99 per night
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Winter winter cottage rentals

Cottage in Phillips
Soo Lake Hide Away
$115 per night
Cottage in Tony
Luxe Lakeshore Cottage Retreat | Dock | Firepit
$222 per night
Cottage in Birchwood
3 BR, 2 Bath Lake Retreat for Family & Friends
$300 per night
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Cottage in Phillips
Hidden Valley Resort~Butternut
$160 per night
Cottage in Hayward
Bayside Birch Cottage on Nelson Lake
$170 per night
Cottage in Phillips
Rustic 2 bedroom cottage on large lake lot.
$150 per night
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Cottage in Couderay
Chippewa Flowage cottage
$285 per night
Cottage in Tony
Beautiful cottage on Lake Flambeau
$126 per night
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Cottage in Hayward
Northwoods Lily Pad
$255 per night
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Cottage in Hayward
3 Bedroom Cottage With Lake Views
$155 per night
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Cottage in Stone Lake
Serenity Now!
$400 per night
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Cottage in Phillips
Charming Cottage on Wilson Lake
$125 per night
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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?


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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  2. United States
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  4. Sawyer County
  5. Winter