Vacation rentals in Winter

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Top-rated vacation rentals in Winter

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Top guest favorite
A rustic cabin is framed by lush greenery and vibrant foliage, with a winding path leading to the lake. Soft clouds drift across the sky, reflecting warm hues of sunset, creating a serene backdrop within a natural setting.
Cabin in Hayward
4.95 out of 5 average rating, 128 reviews

Glamping Cabin at Loon Lake Guesthouse

Rustic Elegance + Northwoods Flare + Island View Panorama + Fully Electric + Front Porch 10 minutes from Hayward, The Glamping Cabin's spacious semi-open floor-plan has 2 beds, full kitchen, dishes, utensils and a thoughtfully designed camp-style water system. Winter days are warm+cozy with the Row-0-Flames heater. Showers are outdoors when temperatures are above 32 degrees or next door at Loon Lake Guesthouse when its cold out. Your "toilet" is a colorful outdoor privy. Fully electric with WiFi

Top guest favorite
Home in Ladysmith
4.95 out of 5 average rating, 255 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

Top guest favorite
The modern cabin features a covered deck with ample seating, including bright red Adirondack chairs positioned around a fire pit. Large windows display warm ambient lighting within, while smoke gently rises from the roof, blending with the surrounding woods.
Cabin in Hayward
4.99 out of 5 average rating, 227 reviews

Hayward Haus, Modern Design w/ Classic Experience

Built as a winter or summer escape for a couple or small group, this beautiful four season cabin is a great way to experience the Northwoods of Wisconsin in a modern, well-appointed, aesthetically rich space designed with relaxation in mind This cabin was built in 2021 and host is 13 year "superhost" This is a default "no pets" cabin, however exceptions can be made with permission and a fee. Inquire with host. NEMA 15-40R outlet provided for level 2 EV charging. You bring chord and adapter.

Top guest favorite
Cabin in Hayward
4.98 out of 5 average rating, 128 reviews

Seeley Oaks A-Frame | Couples Winter Getaway

This is a cabin-in-the-woods experience! The Seeley Oaks A-Frame is our slice of the peaceful Northwoods experience. It's on 40 private, tranquil acres (no neighbors!) with great access to all the Hayward-Cable area has to offer. It's small - intended for two adults, with the option of 2 addtl kids. It's a total of 700 sq ft, with a queen bed in the loft, in-floor heat, full kitchen, and washer and dryer. Less than 2 mi from Highway 63, 8 mi from Cable, and 10 mi from Hayward. IG: @Seeleyoaks

Top guest favorite
A rustic cabin is nestled among lush greenery, showcasing a wooden exterior and a steeply angled roof. The cabin features two skylights on the upper level and a welcoming front porch, surrounded by well-maintained landscaping and natural foliage.
Cabin in Ladysmith
4.93 out of 5 average rating, 372 reviews

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 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.

Guest favorite
The cabin entrance is framed by trees, adorned with string lights and lanterns on the pathway. A wooden bench is visible on the porch, inviting relaxation in the serene surroundings. Soft lighting creates a peaceful ambiance in the evening setting.
Cabin in Hayward
4.89 out of 5 average rating, 482 reviews

Fancy Fireflies-Charming studio Cabin in Hayward

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 cozy, studio size cabin with one queen bed, a bathroom, a kitchenette with a mini-fridge, microwave, Keurig coffeemaker & outdoor grill.

Top guest favorite
A welcoming interior features a large wooden archway that transitions between spaces. A cozy seating area is furnished with a comfortable sofa, with a soft throw draped across it. The room is illuminated by string lights, with a rustic stone fireplace adding charm.
Cottage in Rice Lake
4.98 out of 5 average rating, 125 reviews

Stonehaven Cottages The Turtle cottage

Slow and steady wins the race! We are tickled to introduce our second cottage "The Turtle" here at Stonehaven Cottages on Tuscobia Lake, LLC. We put in a large archway in the vaulted ceiling to give it a look and feel of being inside a turtle shell. This cozy cottage has an open concept with full kitchen, one small bedroom and a queen sofa sleeper. It also has a spectacular view of Tuscobia Lake! When life gets too busy, come and slow down a bit at "The Turtle"!

Superhost
A rustic yurt is surrounded by trees, showcasing a wooden deck with railings. The exterior is covered in green fabric, and a wooden door with a window invites entry. Natural stones are positioned around the base, blending the structure with the forest environment.
Yurt in Cable
4.9 out of 5 average rating, 398 reviews

Cable Rustic Yurt

Explore thousands of acres of public forest land and enjoy endless miles of some of the best recreational trails Wisconsin has to offer. Step out of the yurt, located in the middle of Bayfield County Forest land, and right onto CAMBA mountain bike trails and the North End ski trails (which connect to the American Birkebeiner ski trails). This is a rustic, minimally maintained yurt so come prepared to relax, unwind and explore the wonders of the north woods.

Superhost
Two rustic cabins are shown, featuring dark wooden exteriors with a contrasting metal roof. Each cabin has a front porch with wooden railings and is set on a gravel surface. Lush green grass surrounds the cabins, with trees visible in the background.
Tiny home in Weyerhaeuser
4.8 out of 5 average rating, 107 reviews

Relaxing fun bunk house 1

When you need a break from trail riding the best ATV and snowmobile trails in Northern WI, hiking the beautiful Bluehills Ice Age trail, downhill skiing at Christie Mountain, or hunting and fishing...do it with us in these unique and beautiful cabins. There are three wonderful Restaurants/Bars within walking distance from the front door. Weyerhaeuser also has a wonderful park with a playground, ball fields, and a six pickle ball courts.

Guest favorite
A warm and inviting bedroom features a wooden wall design with natural light streaming through multiple windows. A queen-size bed, adorned with a patterned quilt, sits prominently in the space. Nearby, a small dining table and chair complement the cozy decor.
Guesthouse in Cable
4.87 out of 5 average rating, 154 reviews

The Bear Den

The Bear Den is a beige/green trim home with a perfect location for all your outdoor ventures, located on the corner of Hwy 63 and Leonard School Rd between Seeley and Cable, WI. This 2- bedroom, 1 1/2 bath unit features Northwoods decor. Relax in private backyard with firepit, free firewood, a gas grill and outdoor furniture. Convenience cooking only with restaurants, gas and grocery shopping nearby Cable, WI, or Seeley, WI.

Top guest favorite
A cozy bedroom features a quilted bedspread in red and black patterns atop a spacious bed. A nightstand with a lamp is positioned beside the bed. Natural light enters the room through a window adorned with blue curtains, and wood paneling adds warmth to the space.
Guest suite in Spooner
4.9 out of 5 average rating, 364 reviews

Black Dog Woodland Suite

The Woodland Suite is located on our 10 acre property on Spooner Lake. The Suite is a ground level apartment (300 sf) that is part of our garage/guest building. The views are of tamarack marsh, pine and oak woods, and the lake. It is a three room retreat for couples, solo adventurers, families with kids, and dogs. The Suite is not a good fit for four (4) adults.

Top guest favorite
The living area features a plush gray sofa with a light throw draped over it, complemented by a wooden armchair. A small dining table with four chairs is visible, while natural light filters through sheer curtains covering a nearby window. A television is mounted on the wall opposite the sofa.
Home in Exeland
4.98 out of 5 average rating, 130 reviews

Cozy Northwoods Getaway

Our cozy, updated, one-bedroom cottage in Northwestern Wisconsin is the perfect place from which to launch your Northwoods adventures. It is located very close to several lakes and rivers which are great for boating, kayaking, and fishing. The home is within a few miles from several highways that lead to all the adventures that northwestern Wisconsin has to offer.

Popular amenities for Winter vacation rentals

All about 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?

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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