Holiday rentals in Winter

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Top-rated holiday rentals in Winter

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Top guest favourite
Two hanging chairs are suspended from a rustic wooden frame adorned with string lights, creating a warm glow. A fire pit made of stones is positioned below the chairs, surrounded by a wooded setting. A cabin can be seen in the background, softly illuminated through its window.
Cabin in Hayward
4.94 out of 5 average rating, 323 reviews

The Timberjack

Although it's a rustic homage to the lumberjacks and jills of yesteryear, this cabin includes many of the comforts we now enjoy including a queen bed, kitchenette with fridge, hot water, AC/heat, a Keurig coffeemaker, smart TV and charcoal grill. The Timberjack is surrounded by trees right on Lake Hayward and close to downtown Hayward. Launch your canoe just steps from the cabin, walk into town for lunch, or go hiking or skiing on the nearby trails, this cabin is nestled in the ideal location!

Top guest favourite
Cabin in Comstock
4.97 out of 5 average rating, 231 reviews

Nordic Lake Cabin : Sauna/Hot Tub/Pontoon Rental

We finished building this modern Scandinavian cabin in spring 2020. It’s been featured in Vogue and on Magnolia Network. The cabin sits at the end of the road on a private lot with a perfect view of sunsets over the nature side of the lake. Drive past farm fields, into the woods, and onto our private gravel road, arriving at the driveway. Watch loons, tundra swans, eagles, beavers and deer while you relax by the lake. Pontoon boat rental is available as an add on! Pets welcome for a $90 fee!

Top guest favourite
Cabin in Hayward
4.98 out of 5 average rating, 132 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, 374 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
4.96 out of 5 average rating, 103 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

Guest favourite
The exterior of Fischers’ Trap N’ Fish Motel is displayed, highlighting a large sign with the motel's name and contact information. The building's front features a welcoming façade surrounded by greenery, showcasing a serene and inviting environment.
Flat in Winter
5 out of 5 average rating, 5 reviews

Trap N' Fish Motel Room 3

Welcome snowmobilers! We have plenty of trailer parking, ride snowmobile right up to your door, trail just seconds away, and hot food across the road! Ask us how you can rent the entire motel for large groups for a discounted rate! Sleeps 4. 1 bedroom with full kitchen, bathroom, and living room. Soap and towels included. 1 Bedroom includes 1 queen bed. Living Room includes a day bed that sleeps 1 and a futon that sleeps 1. Rollaway bed to sleep 5 upon request. Roku and Wifi included.

Top guest favourite
The exterior of the guesthouse features vibrant orange siding complemented by blue trim and windows. A sturdy wooden staircase leads to the main entrance, flanked by lush green vegetation. The overall architecture showcases a blend of modern and rustic design elements, inviting guests to explore further.
Flat in Hayward
4.93 out of 5 average rating, 247 reviews

THE SUNROOM SUITE @Loon Loon Lake Guesthouse

Only 10 minutes and a world away from Hayward, the stylishly appointed SUNROOM SUITE is part of Loon Lake Guesthouse. Take in the view of gardens, tall pines and glimmering Loon Lake through windows and skylights that overlook this picturesque setting. Summertime brings swimming, canoeing, bird watching and walking the loop. Venture out for some day tripping or work remotely with Starlink WiFi. And be sure to make time for luxuriating in the soaking tub. Life is sweet in The Sunroom.

Guest favourite
A modern cabin is set among tall trees, featuring a spacious wooden deck with stairs leading up to it. Large windows offer views into the interior, while warm lighting creates a welcoming atmosphere as dusk approaches.
Cabin in Park Falls
4.9 out of 5 average rating, 101 reviews

National Forest Lakeside Retreat

Escape to this beautiful cabin nestled in the woods on a serene lake. With its cozy layout and large windows, you'll feel right at home surrounded by nature's beauty. Enjoy breathtaking views of the dark sky at night and wake up to the peaceful sounds of the National Forest. Explore endless adventures with hiking, ATV, and snowmobile trails just steps away. Unwind on the deck and take in the tranquility of this hidden gem. Book your getaway now and experience the ultimate retreat.

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, 129 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"!

Guest favourite
A warm living area features a large leather sofa adorned with a yellow throw. A wooden coffee table sits at the center, surrounded by a soft rug. Sliding glass doors lead to an outdoor view, while natural wood walls enhance the rustic charm.
Cabin in Birchwood
4.92 out of 5 average rating, 230 reviews

Lakefront Sunset Cabin w/Boats, Spa, FirePit & BBQ

Extraordinary lakefront home, private lake access! Bring your own boat, or use one of ours! Relax on the screened-in patio while watching lake wildlife. BBQ on our charcoal grill, then enjoy a game of cornhole or SpikeBall near the lakeside firepit. Cast a line for great fishing right out front, or push the boats in the water and explore Birch Lake. After a full day, wind down in the hot tub - which is available for you to enjoy year round!

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, 388 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.

Guest favourite
A cozy living area features large windows that allow natural light to flood the space. A stone fireplace is complemented by wooden accents. Comfortable seating includes a blue armchair and a plush ottoman, creating an inviting spot to relax and enjoy the surrounding views.
Cottage in Hayward
4.92 out of 5 average rating, 115 reviews

Bayside Birch Cottage on Nelson Lake

Welcome to the Bayside Birch Cottage in the Northwoods of Hayward, Wisconsin! Our beautiful, cozy spot on Nelson Lake offers a perfect blend of year-round, family-friendly relaxation and adventure - there's truly something for everyone! We’re only 7 minutes from downtown Hayward, so you can also explore shops, restaurants, recreation rentals and trails, and even the giant Muskie statue!

Popular amenities for Winter holiday rentals

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