Holiday rentals in Winter

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Top-rated holiday rentals in Winter

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Top guest favourite
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 favourite
Home in Ladysmith
4.95 out of 5 average rating, 256 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 favourite
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 favourite
Cabin in Hayward
4.98 out of 5 average rating, 129 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 favourite
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, 373 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.

Top guest favourite
An outdoor seating area showcases comfortable green adirondack chairs arranged around a stone firepit, with a fire actively burning. A wooden structure is visible in the background, surrounded by lush greenery and tall trees, creating a serene natural setting.
Chalet in Hayward
4.97 out of 5 average rating, 99 reviews

Sylvan Chalet, Modern, Lakefront, Close to Trails

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. Cabin is brand new as of January 2024. Host is 14 year "superhost" This is a default "no pets" cabin, however certain sizes and breeds are allowed by permission only. We have a NEMA 15-40R outlet for level 2 EV charging. You bring chord and adapter

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 favourite
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, 127 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
4.81 out of 5 average rating, 108 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 favourite
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.
Guest house 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 favourite
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 holiday rentals

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Sawyer County
  5. Winter