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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 Hayward
The Timberjack
Although it's a rustic homage to the lumberjacks and jills of yesteryear, this cabin includes many of the comforts we now enjoy including a queen bed, kitchenette with fridge, hot water, AC/heat, a Keurig coffeemaker, smart TV and charcoal grill. The Timberjack is surrounded by trees right on Lake Hayward and close to downtown Hayward. Launch your canoe just steps from the cabin, walk into town for lunch, or go hiking or skiing on the nearby trails, this cabin is nestled in the ideal location!
$90 per night
SUPERHOST
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.
$252 per night
SUPERHOST
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
SUPERHOST

Winter cabin rentals

Cabin in Hayward
Private Home on Upper Twin Lake, Close to Trails
$125 per night
SUPERHOST
Cabin in Winter
Loons Nest Cabin on Private Lake
$159 per night
SUPERHOST
Cabin in Winter
Waterfront cabin on Connor’s Lake. Sleeps 6
$196 per night
SUPERHOST
Cabin in Winter
Hemlock Haven Resort 2
$185 per night
SUPERHOST
Cabin in Ojibwa
NEW! Wildwood Escapes-Chippewa River Cabin
$186 per night
Cabin in Hayward
Honey Bear Hideaway-cabin in the heart of Hayward
$84 per night
SUPERHOST
Cabin in Weirgor
Cozy Cabin on 10 Acres, Walk to Chippewa River!
$147 per night
Cabin in Ladysmith
Flaming Torch Lodge
$133 per night
SUPERHOST
Cabin in Ojibwa
Cabin #3 - Two bedroom cabin on the water
$129 per night
Cabin in Hayward
The Seeley Oaks A-Frame
$190 per night
SUPERHOST
Cabin in Birchwood
Lakefront Sunset Cabin w/Boats, Spa, FirePit & BBQ
$283 per night
SUPERHOST
Cabin in Hayward
Fancy Fireflies-Charming studio Cabin in Hayward
$87 per night
SUPERHOST

Christmas cabin rentals in Winter

Cabin in Hayward
Lakeshore Lily Pad
$85 per night
SUPERHOST
Cabin in Winter
Hemlock Haven Resort 4
$225 per night
SUPERHOST
Cabin in Hayward
"Das Blockhaus" - cozy, authentic German log cabin
$96 per night
SUPERHOST
Cabin in Exeland
Lakeside Northwoods Retreat
$165 per night
SUPERHOST
Cabin in Hayward
The Bears Den! 2 Premier Lakes within 1 Mile!
$155 per night
Cabin in Hayward
Cozy Cabin on Secluded Peninsula
$141 per night
SUPERHOST
Cabin in Stone Lake
Private Beachfront at Sand Lake Serendipity
$216 per night
SUPERHOST
Cabin in Cameron
Cabin 2 - Northwoods themed 1 BR, lakefront cabin.
$91 per night
SUPERHOST
Cabin in Cable
Hygge House
$119 per night
SUPERHOST
Cabin in Stone Lake
Slice of Paradise on Slim Lake
$135 per night
SUPERHOST
Cabin in Hayward
Muskie Ridge
$226 per night
SUPERHOST
Cabin in Hayward
Cozy 2BR tiny Cabin in the Woods
$111 per night

Winter winter cottage rentals

Cottage in Phillips
Soo Lake Hide Away
$130 per night
Cottage in Hayward
Bayside Birch Cottage on Nelson Lake
$183 per night
SUPERHOST
Cottage in Hayward
Wildwood Escapes-Acorn Shores Cottage
$146 per night
SUPERHOST
Cottage in Medford
Cozy A-frame on Clear Lake
$138 per night
SUPERHOST
Cottage in Tony
Luxe Lakeshore Cottage Retreat | Dock | Firepit
$230 per night
SUPERHOST
Cottage in Birchwood
3 BR, 2 Bath Lake Retreat for Family & Friends
$308 per night
SUPERHOST
Cottage in Phillips
Hidden Valley Resort~Butternut
$175 per night
Cottage in Hayward
Northwoods Lily Pad
$255 per night
SUPERHOST
Cottage in Iron River
Willow North Cottage in Iron River, Wisconsin
$168 per night
SUPERHOST
Cottage in Hayward
Whispering Pines Hideaway located on Lake Gurno
$200 per night
Cottage in Couderay
Chippewa Flowage cottage
$285 per night
Cottage in Stone Lake
Serenity Now!
$500 per night
SUPERHOST

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.

Other types of stays on Airbnb

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Sawyer County
  5. Winter