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.

Cabin · 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.
Aug 28 – Sep 4
$119 per night
Superhost
Cabin · 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.
Feb 8 – 15
$78 per night
Superhost
Cabin · Winter
Loons Nest Cabin on Private Lake
This property showcases Perch Lake in a panoramic view. Whether you are sitting on the deck or on the dock you can observe picturesque sunrises and sunsets while observing Lake wildlife. Sawyer County ATV/Snowmobile trails are minutes away and accessible from the property.
Jul 13 – 20
$143 per night
Superhost

Vacation rentals for every style

Get the amount of space that is right for you

  • Cabins
  • Cottages
  • Unique stays

Winter cabin rentals

Cabin · Winter
Connors Lake Cabin
Dec 2 – 9
$258 per night
Cabin · Ojibwa
BOOKING FALL NOW|Riverview Oasis 3/4 mi to trails
Dec 8 – 15
$165 per night
Superhost
Cabin · Hayward
Hayward Haus, Modern Design w/ Classic Experience
Jul 4 – 11
$456 per night
Superhost
Cabin · Exeland
Lakeside Northwoods Retreat
Dec 1 – 8
$143 per night
Superhost
Cabin · Winter
Hemlock Haven Resort 4
Jun 29 – Jul 6
$164 per night
Superhost
Cabin · Hayward
Hayward Four Season Moose Lake Getaway
Sep 8 – 15
$165 per night
Cabin · Park Falls
Oxbo Resort - Cabin 1
May 9 – 16
$95 per night
Superhost
Cabin · Hayward
Lovely Private Lakefront Retreat, Near Hayward
Jan 18 – 25
$169 per night
Superhost
Cabin · Radisson
Waterfront cabin on the Radisson Flowage
May 30 – Jun 6
$225 per night
Cabin · Couderay
Tainter Cabins -15 miles to Hayward (Northwoods)
Aug 9 – 16
$158 per night
Superhost
Cabin · Hayward
*Beautiful Log Cabin with Sauna*
Apr 14 – 21
$315 per night
Cabin · Park Falls
Oxbo Resort - Cabin 2
Jan 16 – 23
$127 per night
Superhost

Christmas cabin rentals in Winter

Cabin · Couderay
3-bedroom Cabin on Crystal Clear Blueberry Lake
Aug 5 – 12
$274 per night
Superhost
Cabin · Weirgor
House on 10 Acres Overlooking Chippewa River!
May 23 – 30
$158 per night
Cabin · Hayward
“Restful Retreat” Three Bedroom on Chip Flowage
Apr 2 – 9
$143 per night
Superhost
Cabin · Ladysmith
"Little house on the Flambeau"
May 8 – 15
$119 per night
Cabin · Park Falls
Oxbo Resort - Cabin 4
Mar 26 – Apr 2
$127 per night
Superhost
Cabin · Hayward
Cozy log cabin on 6 acres
Nov 8 – 15
$189 per night
Superhost
Cabin · Hayward
K&K’s Lakeside Lodge- Hayward Relaxing Getaway
Dec 15 – 22
$193 per night
Superhost
Cabin · Hayward
Entire lake to yourself at this secluded cabin!
Sep 4 – 11
$275 per night
Superhost
Cabin · Hayward
Muskie Ridge: February Special $125 per night!
Jan 13 – 20
$249 per night
Superhost
Cabin · Hayward
Cabin #3, Musky Joe's Resort, Hayward, WI
Mar 17 – 24
$103 per night
Superhost
Cabin · Hayward
Northern Comfort on Lovejoy - Hayward, WI
Mar 3 – 10
$160 per night
Superhost
Cabin · Hayward
Cabin 5 on beautiful Round Lake Grand Pines Resort
Apr 24 – May 1
$149 per night

Winter winter cottage rentals

Cottage · Tony
Beautiful cottage on Lake Flambeau
Oct 30 – Nov 6
$97 per night
Superhost
Cottage · Couderay
Chippewa Flowage cottage
Mar 3 – 10
$285 per night
Cottage · Hayward
Gritzy's Round Lake Retreat
Nov 12 – 19
$144 per night
Cottage · Tony
Luxe Lakeshore Cottage Retreat | Dock | Firepit
Mar 8 – 15
$222 per night
Cottage · Couderay
Cozy Cottage on Blueberry Lake
Dec 4 – 11
$179 per night
Cottage · Hayward
Newly renovated lake cottage w/King suite + kayaks
Jul 13 – 20
$347 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