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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.

Home in Ladysmith
North Country Cottage
This beautiful, recently renovated home is out in the country down a dead-end road, but still only a few miles from the town of Ladysmith. It is about a mile from a little county park on the Dairyland Reservoir, only a few miles from the local golf course, and just down the road from hopping on the snowmobile trail in the winter. There is a boat landing at the park for summer and access to ice fishing in the winter. We hope to earn 5*s and look forward to hosting you! State License #VJAS-BCCLDB
$100 per night
Cabin in Hayward
Lakeshore Lily Pad
Surrounded by trees, settled right on Lake Hayward sits this charming & cozy cabin in a little cabin community less than half a mile from downtown Hayward. Launch your canoe just steps from the cabin's entrance, bike into town for lunch, or go hiking or skiing on the nearby trails, this cabin is nestled in the perfect location! This is a studio size cabin with one queen bed, sofa (with pull-out queen mattress), bathroom, kitchenette with a fridge, microwave, Keurig coffeemaker & outdoor grill.
$89 per night
Cabin in Ladysmith
Flaming Torch Lodge
This is a quaint little cabin on the Flambeau River just outside of Ladysmith, WI (flambeau translastes to flaming torch) It is clean and newly remodeled. It has a fully equipped kitchen, stove and fridge. A gas fireplace is the centerpiece of the living room space. Snuggle up on the leather sofa or recliner, turn on the fireplace, grab a good book, hot chocolate and relax. There is one bedroom with a memory foam mattress. A loft with a sleeper couch. No pets and no smoking at any time please.
$132 per night

Other great vacation rentals in Winter

Home in Mason
Marengo River Cabin
$142 per night
Apartment in Hayward
Sunset Lake View Apt Callahan Lake
$123 per night
Cabin in Hayward
Vintage 1940's Hayward Cabin!
$169 per night
Cabin in Cable
The Cable Cabin - Walk to Downtown Cable
$138 per night
Home in Winter
Bungalow Trail
$110 per night
Cabin in Winter
Bobbers Cabin on Private Lake
$140 per night
Guesthouse in Ojibwa
ATV/Side by Side enthusiasts! Private rd.
$90 per night
Apartment in Winter
Gateway to the Great North Woods by DonBar
$115 per night
Home in Exeland
Cozy Northwoods Getaway
$92 per night
Cabin in Winter
Hemlock Haven Resort 1
$165 per night
Cottage in Phillips
Soo Lake Hide Away
$130 per night
Cabin in Winter
Connor’s Lake, near UTV trails, WiFi, sleeps 6
$159 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?

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.

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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  2. United States
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  4. Sawyer County
  5. Winter