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, 253 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

Guest favorite
The cabin is illuminated by string lights, creating a warm ambiance. A circular seating area with two chairs surrounds a communal firepit on a wooden deck. The cabin features rustic wood siding with a welcoming entrance, surrounded by trees and a gravel area for outdoor activities.
Cabin in Hayward
4.95 out of 5 average rating, 239 reviews

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.

Top guest favorite
The cabin's exterior is framed by vibrant autumn foliage, showcasing a blend of wood and metal materials. A screened porch is visible at the front, while a natural stone and pebble landscape surrounds the foundation. The expansive yard offers a peaceful retreat atmosphere.
Cabin in Winter
4.95 out of 5 average rating, 38 reviews

Northwoods Cabin

Peaceful retreat in the Wisconsin Northwoods. Well designed and stylish cabin on two wooded acres. Just steps to the Chippewa River. Fully equipped kitchen, 2 full bathrooms and 2 beds on the second floor loft. High speed internet, electric car charger available. ***In winter months, the road/driveway to the cabin are plowed when there is 6+ inches of snow. AWD vehicles are recommended during snow season.*** A shovel is provided in case guests need to shovel path from vehicle to front door.***

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, 224 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, 127 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, 371 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.

Superhost
The exterior of a recently remodeled house is shown, featuring a stone chimney and a metal roof. Lush green grass surrounds the house, and trees are visible in the background. A welcoming front porch is framed by a large window.
Home in Loretta
4.83 out of 5 average rating, 6 reviews

Charming home near Loretta

Get ready to relax in this recently remodeled house. There is 1 king bed, 1 queen bed, and a sofa bed perfect for a cozy getaway. We are conveniently located on Hwy 70. We are minutes from the Tuscobia Trail, 7 min. from Winter and 5 min. from Loretta. We have seen deer, turkey, grouse and other wildlife including bugs. We do NOT have WIFI available. T-mobile/verizon have good service. We do ask that guests take their trash with them. There is space to park your trailer.

Top guest favorite
The charming cottage exterior features wooden siding and a sloped roof with a dormer window. Flower baskets hang from the porch posts, adding color to the serene landscape. A gravel pathway leads to the entrance, framed by natural stone landscaping and lush greenery.
Cottage in Rice Lake
4.99 out of 5 average rating, 197 reviews

Stonehaven Cottages on Tuscobia Lake LLC.

The "Gatekeeper" cottage has a natural gas stone fireplace in the living room, Full size sofa sleeper, full kitchen, full bath on the main floor and a half bath in the sleeping loft. (Need to be able to climb ladder stairs to lofted bedroom). A spiral staircase leads you down to the lower level which has an additional bedroom, queen sofa sleeper in the extra living room space, and full bathroom. The lower level also has a walk out french door to the patio area.

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, 397 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, 103 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.

Top guest favorite
The peaceful cabin is nestled on a spacious lawn surrounded by trees displaying autumn colors. A covered patio with seating options faces the yard, and a charcoal grill is visible nearby. The structure features a simple, rustic design under a clear blue sky.
Cabin in Winter
5 out of 5 average rating, 32 reviews

Reelaxation Cabin on Lake Winter

Reelax with the whole family at this peaceful reelaxation cabin on Lake Winter. Reel in the 'big one' fishing off the private dock, kayak, paddle board, canoe, or rowboat the lake, and then reelax on the patio with a fire watching the mystic Lake Winter. Reelaxation cabin is a two-bedroom one large bath cozy cabin in Northern Wisconsin with an open floor plan all on one level with no steps.

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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