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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.

Family Cabin on the Chippewa River
Entire cabin · 8 guests · 4 beds · 3 baths
Family Cabin on the Chippewa RiverBring the whole family to this great place with lots of room for fun.
Paradise Pines
SUPERHOST
Entire cabin · 4 guests · 1 bed · 1 bath
Paradise PinesQuiet, 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, downtown area with many small shops and candy/ice cream parlors, freshwater fishing hall of fame, and night life.
Hemlock Haven Resort 2
SUPERHOST
Entire cabin · 4 guests · 2 beds · 1 bath
Hemlock Haven Resort 2Our 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.

Vacation rentals for every style

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Winter cabin rentals

SUPERHOST
  1. Entire cabin
  2. Hayward
Hayward Haus, Modern Design w/ Classic Experience
$253 per night
  1. Entire cabin
  2. Winter
Connors Lake Cabin
$300 per night
SUPERHOST
  1. Entire cabin
  2. Ladysmith
Flaming Torch Lodge
$102 per night
SUPERHOST
  1. Entire cabin
  2. Ojibwa
Secluded River Cabin near Hayward w/ WiFi, Kayaks
$181 per night
SUPERHOST
  1. Entire cabin
  2. Hayward
Cabin #2, Musky Joe's Resort, Hayward, WI
$100 per night
SUPERHOST
  1. Entire cabin
  2. Hayward
Private Home on Upper Twin Lake, Close to Trails
$155 per night
SUPERHOST
  1. Entire cabin
  2. Winter
Hemlock Haven Resort 4
$225 per night
SUPERHOST
  1. Entire cabin
  2. Hayward
Spider Creek Country Cottage
$81 per night
SUPERHOST
  1. Entire cabin
  2. Hayward
Muskie Ridge: February Special $125 per night!
$175 per night
SUPERHOST
  1. Entire cabin
  2. Exeland
Lakeside Northwoods Retreat
$130 per night
  1. Entire cabin
  2. Hayward
Aspen Cabin-Lost Land Lake Waterfront Getaway
$110 per night
SUPERHOST
  1. Entire cabin
  2. Hayward
Cabin #5 on the Chippewa Flowage
$150 per night

Vacation rentals near Winter

SUPERHOST
  1. Entire residential home
  2. Winter
Bungalow Trail
$99 per night
SUPERHOST
  1. Entire rental unit
  2. Winter
Gateway to the Great North Woods by DonBar
$95 per night
SUPERHOST
  1. Entire residential home
  2. Winter
Private lake home on small lake that allows motors
$160 per night
SUPERHOST
  1. Entire residential home
  2. Winter
Northwoods Tranquility awaits on Blaisdell Lake
$285 per night
SUPERHOST
  1. Entire residential home
  2. Winter
Bears Den Cabin on Private Lake
$320 per night
SUPERHOST
  1. Entire cabin
  2. Ojibwa
Cabin #3 - Two bedroom cabin on the water
$160 per night
  1. Entire cottage
  2. Winter
NEW! Wisconsin Community Cottage w/ Charcoal Grill
$89 per night
No reviews yet
  1. Island
  2. Winter
Exclusive PRIVATE ISLAND-for your group-LakeWinter
$699 per night
  1. Entire cabin
  2. Winter
NOW BOOKING FOR BIRKIE STAY IN HISTORIC LODGE
$1,200 per night
No reviews yet
  1. Entire cabin
  2. Hunter
Chippewa View Lodge
$1,181 per night
No reviews yet
  1. Entire cabin
  2. Hayward
Welcome to the Aspen.
$350 per night
  1. Entire cottage
  2. Winter
NEW! Cozy Pet-Friendly Winter Cottage in Community
$89 per night

Winter winter vacation rentals

SUPERHOST
  1. Entire residential home
  2. Winter
Bungalow Trail
$99 per night
SUPERHOST
  1. Entire rental unit
  2. Winter
Gateway to the Great North Woods by DonBar
$95 per night
  1. Entire cabin
  2. Winter
Family Cabin on the Chippewa River
$206 per night
SUPERHOST
  1. Entire cabin
  2. Winter
Hemlock Haven Resort 2
$185 per night
SUPERHOST
  1. Entire cabin
  2. Winter
Hemlock Haven Resort 1
$165 per night
SUPERHOST
  1. Entire cabin
  2. Winter
Paradise Pines
$90 per night
SUPERHOST
  1. Entire cabin
  2. Winter
Loons Nest Cabin on Private Lake
$142 per night
SUPERHOST
  1. Entire residential home
  2. Winter
Private lake home on small lake that allows motors
$160 per night
SUPERHOST
  1. Entire cabin
  2. Ojibwa
Secluded River Cabin near Hayward w/ WiFi, Kayaks
$181 per night
SUPERHOST
  1. Entire cabin
  2. Winter
Hemlock Haven Resort 4
$225 per night
SUPERHOST
  1. Entire residential home
  2. Winter
Northwoods Tranquility awaits on Blaisdell Lake
$285 per night
SUPERHOST
  1. Entire residential home
  2. Winter
Bears Den Cabin on Private Lake
$320 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?


How do I get around Winter?

You will most likely need a car to get to Winter and the natural attractions that surround the town. Neither Amtrak nor Greyhound operate lines through this corner of the Northwoods, and the two most convenient airports are Rhinelander-Oneida County Airport (RHI), which is 90 miles west from Winter, and the much bigger Minneapolis-St. Paul International Airport (MSP), which is 160 miles to the northeast, or about a three-hour drive. Once you’re here, however, Namekagon Transit does operate accessible, door-to-door bus service around Sawyer County — worth considering if you’re headed to a nearby lodge or restaurant for the evening.


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.