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, 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 favourite
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 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, 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 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, 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.

Top guest favourite
A charming log cabin is surrounded by tall trees, with a stone pathway leading to the front porch. The exterior features natural wood and a sloped roof, blending harmoniously with the wooded landscape.
Cabin in Hayward
4.96 out of 5 average rating, 199 reviews

Cozy 2 bedroom cabin on the water - must see!!

Enjoy a quiet, relaxing week in the north woods of Hayward, WI! Our 2 bedroom, 2 bath cabin sleeps six comfortably (2 queen beds and a futon). Cabin is two levels and 1500 square ft. The cabin is located on the Namekagon River with direct access to Hayward Lake and the public boat launch just a few hundred feet away. You really get the best of both worlds here as the cabin is tucked away in a private, wooded area but is also walking distance to downtown Hayward and other attractions!!

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.

Top guest favourite
A charming cabin with wooden siding is surrounded by colorful autumn foliage. The exterior features large green windows and a decorative quilt pattern on the front wall, indicating a welcoming atmosphere. A slight lawn leads towards the porch, offering a view of the nearby lakeside.
Tiny home in Lake Nebagamon
4.96 out of 5 average rating, 440 reviews

Berrywood Acres Cabin

Berrywood Acres is located on the eastern shores of Lake Nebagamon. We are known for beautiful sunsets with quiet surroundings and located minutes from the famous Brule River, great hiking trails nearby and a 35 minute drive from Duluth/Superior or a bit further east to the Bayfield/Ashland area. The cabin is simple with all you need for a little RnR. Come relax on the porch and enjoy the view. We look forward to welcoming you to Berrywood Acres Cabin!

Guest favourite
The exterior of a charming cabin is surrounded by lush greenery, featuring large windows that reflect the evening sky. A hot tub is positioned on a paved area, with a grassy lawn extending toward a playground and the woods in the background.
Cabin in Ojibwa
4.93 out of 5 average rating, 107 reviews

Seclusion, Avail Christmas-Hot Tub, WIFI, 2 Kings

Escape to Chippewa River Cabin, a stylish Scandinavian retreat in the heart of Wisconsin's Northwoods. With 3 bedrooms, full coffee bar, a Pacman game console and a cozy double-sided fireplace, this chic cabin offers a perfect blend of comfort and luxury. Unwind in the open layout, surrounded by breathtaking views of the river and 10 acres of private property. Whether you're seeking peace and solitude or adventure and excitement, this place is for you!

Guest favourite
An outdoor seating area is surrounded by trees, featuring a round metal table with chairs. The cabin, characterized by large windows and a welcoming entrance, is positioned nearby, with steps leading up to the porch. A fire pit area is also visible in the background.
Cabin in Cumberland
4.86 out of 5 average rating, 185 reviews

Cozy Cabin on Kirby Lake - Stuga Wald

Enjoy the peace and quiet of this quaint little cabin on Kirby Lake. If you are looking for rest and retreat, this place is for you! The cabin is open concept with the living space, dining, kitchen, and bathroom on the main level. The loft boasts two twin beds that each pull out into a king, as well as a pull-out couch downstairs. Enjoy the tranquility of a sunset paddle, evening campfire, the call of loons, and the simplicity Stuga Wald has to offer.

Top guest favourite
A cozy interior features a sleeping loft accessed by a ladder, with a spacious couch in the foreground. The kitchenette showcases modern appliances and reclaimed wood accents, while natural light streams through large windows adorned with light-colored curtains.
Tiny home in Lake Nebagamon
4.98 out of 5 average rating, 381 reviews

Cozy Fireplace in a Northwoods Tiny House

Deer Haven is a tiny house (192 sq feet) located in my backyard, overlooking acres of woodland. The space is small and simple. Get to the queen bed in the sleeping loft by climbing the ladder. Bathroom has a toilet and stock tank shower. The kitchen has basic amenities - fridge, microwave, hot plate, griddle, dishes, etc. Best spot in the house is on the couch, where you can see the fireplace and the gorgeous woods out the patio door.

Popular amenities for Winter holiday rentals

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