Skip to content

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.

SUPERHOST
  1. Entire cabin
  2. 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.

ﺩ.ﺇ606 per night
SUPERHOST
  1. Entire cabin
  2. Winter
Waterfront cabin on Connor’s Lake. Sleeps 6

Take a break and unwind at this peaceful oasis on Connor’s Lake. 420 acre lake with excellent fishing for walleye, bass and musky. Quiet, beautiful lake front with gorgeous morning sunrises. Central air. 2 bedroom, one bath, full kitchen, washer/dryer, charcoal grill. 2 full bedrooms which each contain a queen size bed. 2 fold out futons in living room. We are located .5 mile from UTV trails, hiking trails nearby. Pontoon, kayak and canoe rental nearby. No smoking or pets allowed.

ﺩ.ﺇ720 per night
SUPERHOST
  1. Entire cabin
  2. Winter
Family Cabin on the Chippewa River

Bring the whole family to this great place with lots of room for fun.

ﺩ.ﺇ756 per night

Vacation rentals for every style

Get the amount of space that is right for you

  • Cabins
  • Cottages
  • Unique stays

Winter cabin rentals

SUPERHOST
  1. Entire cabin
  2. Ojibwa
BOOKING FALL NOW|Riverview Oasis 3/4 mi to trails
ﺩ.ﺇ958 per night
SUPERHOST
  1. Entire cabin
  2. Winter
Paradise Pines
ﺩ.ﺇ364 per night
SUPERHOST
  1. Entire cabin
  2. Winter
Hemlock Haven Resort 2
ﺩ.ﺇ680 per night
SUPERHOST
  1. Entire cabin
  2. Hayward
Hayward Haus, Modern Design w/ Classic Experience
ﺩ.ﺇ1,350 per night
SUPERHOST
  1. Entire cabin
  2. Winter
Hemlock Haven Resort 4
ﺩ.ﺇ826 per night
SUPERHOST
  1. Entire cabin
  2. Ladysmith
Flaming Torch Lodge
ﺩ.ﺇ473 per night
  1. Entire cabin
  2. Radisson
Waterfront cabin on the Radisson Flowage
ﺩ.ﺇ790 per night
  1. Entire cabin
  2. Hayward
Cozy Cabin in Northwoods Beach
ﺩ.ﺇ367 per night
SUPERHOST
  1. Entire cabin
  2. Hayward
Country Cabin on the Chippewa Flowage, Hayward WI
ﺩ.ﺇ420 per night
  1. Entire cabin
  2. Hayward
Cozy Hartnett Lodge on Lac Courte Oreilles
ﺩ.ﺇ918 per night
SUPERHOST
  1. Entire cabin
  2. Hayward
Cabin #2, Musky Joe's Resort, Hayward, WI
ﺩ.ﺇ367 per night
  1. Entire cabin
  2. Ojibwa
Cabin #3 - Two bedroom cabin on the water
ﺩ.ﺇ458 per night

Christmas cabin rentals in Winter

SUPERHOST
  1. Entire cabin
  2. Hayward
Aspen Cabin-Lost Land Lake Waterfront Getaway
ﺩ.ﺇ672 per night
SUPERHOST
  1. Entire cabin
  2. Hayward
Cabin #3, Musky Joe's Resort, Hayward, WI
ﺩ.ﺇ367 per night
SUPERHOST
  1. Entire cabin
  2. Hayward
Muskie Ridge: February Special $125 per night!
ﺩ.ﺇ915 per night
  1. Entire cabin
  2. Hayward
The Tiger Cat Cabin on Burns Lake Hayward, WI
ﺩ.ﺇ826 per night
  1. Entire cabin
  2. Hayward
Up North Round Lake Retreat
ﺩ.ﺇ1,299 per night
  1. Entire cabin
  2. Ojibwa
Cabin #2 - Two bedroom cabin on the water
ﺩ.ﺇ556 per night
  1. Entire cabin
  2. Hayward
Hayward Cabin on Moose Lake ($50 FUEL CREDIT!!!)
ﺩ.ﺇ866 per night
  1. Entire cabin
  2. Hayward
Northwoods Cabin on Teal Lake
ﺩ.ﺇ470 per night
SUPERHOST
  1. Entire cabin
  2. Hayward
Private Home on Upper Twin Lake, Close to Trails
ﺩ.ﺇ832 per night
  1. Entire cabin
  2. Ladysmith
"Little house on the Flambeau"
ﺩ.ﺇ437 per night
SUPERHOST
  1. Entire cabin
  2. Hayward
“Restful Retreat” Three Bedroom on Chip Flowage
ﺩ.ﺇ551 per night
SUPERHOST
  1. Entire cabin
  2. Hayward
Cabin #5 on the Chippewa Flowage
ﺩ.ﺇ551 per night

Winter winter cottage rentals

  1. Entire cottage
  2. Winter
NEW! Cozy Pet-Friendly Winter Cottage in Community
ﺩ.ﺇ327 per night
SUPERHOST
  1. Entire cottage
  2. Hayward
Diamonds On The Water on Lac Courte Oreilles
ﺩ.ﺇ835 per night
SUPERHOST
  1. Entire cottage
  2. Tony
Beautiful cottage on Lake Flambeau
ﺩ.ﺇ463 per night
  1. Entire cottage
  2. Hayward
All-Season Cottage on beautiful premier Round Lake
ﺩ.ﺇ735 per night
  1. Entire cottage
  2. Couderay
Chippewa Flowage cottage
ﺩ.ﺇ1,047 per night
  1. Entire cottage
  2. Hayward
Gritzy's Round Lake Retreat
ﺩ.ﺇ643 per night
  1. Entire cottage
  2. Winter
NEW! Wisconsin Community Cottage w/ Charcoal Grill
ﺩ.ﺇ327 per night
  1. Entire cottage
  2. Winter
NEW! Inviting Wisconsin Cottage w/ Charcoal Grill!
ﺩ.ﺇ327 per night
  1. Entire cottage
  2. Hayward
Whispering Pines Hideaway located on Lake Gurno
ﺩ.ﺇ735 per night
  1. Entire cottage
  2. Hayward
Newly renovated lake cottage w/King suite + kayaks
ﺩ.ﺇ2,728 per night
  1. Entire cottage
  2. Winter
NEW! Community Winter Cottage w/ Shared Amenities!
ﺩ.ﺇ327 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.

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