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.

Guest favorite

Home in Ladysmith

4.95 out of 5 average rating, 199 reviews

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

Mar 12 – 19

R1,956 ZAR per night
Guest favorite

Guesthouse in Hayward

5.0 out of 5 average rating, 104 reviews

Silent Sports Retreat in Seeley

The dog-friendly Hollywood Hills Chalet is a charming guest cabin that provides opportunities to ski, snowshoe, fat bike, MTB and hike out the door on our neighborhood trail network that is groomed in the winter. In warmer weather, the Namekagon River is less than a mile away and nearby Silverthorn Lake Park in Seeley offers great opportunities to paddle, or just chill on a family-friendly beach. Parking for 2-3 vehicles and a smaller standard trailer. (Nonsmokers only, please and thank you.)

Apr 9 – 16

R2,030 ZAR per night
Guest favorite

Cabin in Ladysmith

4.92 out of 5 average rating, 312 reviews

Flaming Torch Lodge (No Cleaning Fee)

This is a quaint little cabin on the Flambeau River just outside of Ladysmith, WI (flambeau translastes to flaming torch) It is a clean space with rustic charm. It has a fully equipped kitchen, stove and fridge. A gas fireplace is the centerpiece of the living room. Snuggle up on the sofa or recliner, turn on the fireplace, and relax. There is one bedroom with a memory foam mattress. A loft with a sleeper couch. Free amenities, including cleaning. No pets and no smoking at any time please.

Dec 15 – 22

R2,364 ZAR per night

Popular amenities for Winter vacation rentals

Other great vacation rentals in Winter

Guest favorite

Cabin in Hayward

4.99 out of 5 average rating, 149 reviews

Hayward Haus, Modern Design w/ Classic Experience

Mar 9 – 16

R14,105 ZAR per night
Guest favorite

Cabin in Hayward

4.95 out of 5 average rating, 328 reviews

"Das Blockhaus" - cozy, authentic German log cabin

Oct 20 – 27

R2,415 ZAR per night
Superhost

Cottage in Medford

4.84 out of 5 average rating, 295 reviews

Cozy A-frame on Clear Lake

Oct 22 – 29

R2,568 ZAR per night
Guest favorite

Cabin in Trego

4.99 out of 5 average rating, 194 reviews

Wilderness River Boat House

May 13 – 20

R1,945 ZAR per night
Guest favorite

Home in Winter

4.89 out of 5 average rating, 74 reviews

Bungalow Trail

May 12 – 19

R2,396 ZAR per night
Guest favorite

Guesthouse in Ojibwa

4.96 out of 5 average rating, 45 reviews

ATV/Side by Side enthusiasts! Private rd.

Jan 11 – 18

R1,868 ZAR per night
Guest favorite

Apartment in Winter

4.96 out of 5 average rating, 98 reviews

Gateway to the Great North Woods by DonBar

May 24 – 31

R2,259 ZAR per night
Guest favorite

Cabin in Winter

5.0 out of 5 average rating, 14 reviews

Bobbers Cabin on Private Lake

Apr 4 – 11

R3,474 ZAR per night
Guest favorite

Cabin in Winter

5.0 out of 5 average rating, 11 reviews

The Hideaway on Highland

Jan 15 – 22

R4,779 ZAR per night
Superhost

Cabin in Winter

4.91 out of 5 average rating, 22 reviews

Northwoods Cabin

Dec 18 – 25

R3,994 ZAR per night
Guest favorite

Cabin in Winter

4.96 out of 5 average rating, 27 reviews

Lakefront cabin on Connor’s Lake, sleeps 6, WiFi

Feb 11 – 18

R3,860 ZAR per night
Guest favorite

Cabin in Bruce

4.95 out of 5 average rating, 19 reviews

Winding Creek Cabin - next to Christie Mountain!

Apr 22 – 29

R2,630 ZAR 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.

Destinations to explore

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