Cabin and house vacation rentals in Winter

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Top-rated vacation rentals in Winter

Guests agree: these stays are highly rated for location, cleanliness, and more.

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.

"The Whitetail"... Upscale while still Upnorth!"
SUPERHOST
Entire condominium (condo) · 6 guests · 4 beds · 1 bath

"The Whitetail"... Upscale while still Upnorth!"Welcome to "The Condos at Connors Lake!" This three bedroom one bath unit will be sure to keep you comfortable while you are enjoying all of your "Up North" outdoor activities. We are located directly on the snowmobile and ATV trail and offers ample parking for all of your vehicle and trailer needs. The Connors Lake park and boat landing are located within walking distance of the front door. The Lake of the Pines boat landing is less the a mile away for you to enjoy as well.

Private 2 Bedroom Home on 10 Acres
Entire residential home · 3 guests · 0 beds · 1 bath

Private 2 Bedroom Home on 10 AcresMost of the comforts of home are provided in this rural escape tucked among the numerous river access points, trails, and plenty of wildlife. Lake Chippewa, Christie Mountain, State and National forests, as well as the Tuscobia Trail and the Blue Hills all nearby. Our home provides a nice place to relax and prepare dinner after a day of outdoor recreation or simply enjoying you-time. Just a few miles from Hwy 40. Plenty of parking.

Vacation rentals for every style

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Popular amenities for Winter vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Beachfront vacation cabins

  1. Entire cabin
  2. Hayward
Northwoods Cabin on Teal Lake
$215 per night
  1. Entire cabin
  2. Winter
Cozy Northwoods Cabin with private beach access!
$140 per night
  1. Entire cabin
  2. Hayward
cabin for all seasons Lake Lac Courte Oreilles
$150 per night
SUPERHOST
  1. Entire cabin
  2. Exeland
Lakeside Northwoods Retreat
$159 per night
  1. Entire cabin
  2. Hayward
Lakeside cabin in Classic Hayward Resort
$175 per night
  1. Entire cabin
  2. Hayward
Beautiful Lake View on the Chippewa Flowage
$243 per night
  1. Entire cabin
  2. Hayward
Cabin #5 on the Chippewa Flowage
$150 per night
  1. Entire cabin
  2. Hayward
Country Cabin on the Chippewa Flowage, Hayward WI
$150 per night
  1. Entire cabin
  2. Hayward
Cabin #3, Musky Joe's Resort, Hayward, WI
$150 per night
SUPERHOST
  1. Entire cabin
  2. Ojibwa
Spacious two bedroom cabin on the water
$153 per night
  1. Entire cabin
  2. Hayward
Hayward 2 Bedroom Lake Cottage
$200 per night
SUPERHOST
  1. Entire cabin
  2. Ojibwa
Two bedroom cabin on the water
$146 per night

Waterfront cabin rentals

SUPERHOST
  1. Entire cabin
  2. Hayward
Hayward Log cabin retreat
$300 per night
  1. Entire cabin
  2. Hayward
Burns Lake Cabin w/Dock, Fire Pit, Rowboat & More!
$156 per night
SUPERHOST
  1. Entire cabin
  2. Hayward
Spider Creek Country Cottage
$91 per night
  1. Entire cabin
  2. Hayward
1 Bedroom Lakeside Cabin on Teal Lake. YellowBirch
$259 per night
SUPERHOST
  1. Entire cabin
  2. Hayward
Cabin 7 on beautiful Round Lake Grand Pines Resort
$440 per night
SUPERHOST
  1. Entire cabin
  2. Exeland
Pine Point
$165 per night
SUPERHOST
  1. Entire cabin
  2. Hayward
17 Peaceful Acres at Hemlock Lodge on Spider Lake!
$332 per night
SUPERHOST
  1. Entire cabin
  2. Ladysmith
Flaming Torch Lodge
$105 per night
SUPERHOST
  1. Entire cabin
  2. Hayward
Charming Lakeside Cabin in Treehouse Like Setting
$275 per night
  1. Entire cabin
  2. Weirgor
House on 10 Acres Overlooking Chippewa River!
$142 per night
SUPERHOST
  1. Entire cabin
  2. Ojibwa
Clean + Quiet Fall Getaway Cabin w/Fireplace, WIFI
$256 per night
SUPERHOST
  1. Entire cabin
  2. Hayward
K&K’s Lakeside Lodge- Hayward Relaxing Getaway
$390 per night

Pet friendly vacation houses

  1. Entire residential home
  2. Clam Lake
The PineHurst Lodge - Lower Clam Lake -
$185 per night
SUPERHOST
  1. Entire residential home
  2. Hayward
A Chapel in the Woods
$169 per night
  1. Entire residential home
  2. Clam Lake
Trailhead Lodge
$139 per night
  1. Entire residential home
  2. Hayward
Secluded, serene, lake front property - all yours!
$400 per night
SUPERHOST
  1. Entire residential home
  2. Hayward
Clear Your Mind on Clear Lake
$247 per night
SUPERHOST
  1. Entire residential home
  2. Exeland
Cozy Northwoods Getaway
$95 per night
No reviews yet
  1. Entire residential home
  2. Clam Lake
Clam Lake Lodge and Wapiti Cabin
$1,250 per night
SUPERHOST
  1. Entire residential home
  2. Exeland
Swift Creek Cabin
$189 per night
  1. Entire residential home
  2. Clam Lake
Quaint Clam- Upper Clam Lake
$128 per night
SUPERHOST
  1. Entire residential home
  2. Park Falls
Our North Woods Hidden Gem
$125 per night
SUPERHOST
  1. Entire residential home
  2. Winter
Private lake home on small lake that allows motors
$160 per night
  1. Entire residential home
  2. Clam Lake
Cascade is a spacious 3 bedroom, 2.5 bath home overlooking Lower Clam Lake
$307 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 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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