Holiday rentals in Winter

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Winter

Guests agree: these stays are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
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, 129 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

Guest favourite
The cabin exterior features a rustic wooden design, complemented by a welcoming front porch. A picnic table and bench offer outdoor seating, while potted plants embellish the entryway. The entrance door includes a decorative bear motif, enhancing the natural surroundings.
Cabin in Hayward
4.89 out of 5 average rating, 374 reviews

Honey Bear Hideaway Cabin

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 and a bunk bed with 2 twin mattresses, bathroom, kitchenette with a fridge, microwave, Keurig coffeemaker & outdoor grill.

Top guest favourite
A log cabin situated amidst tall trees features a spacious deck equipped with a dining table and four red chairs. A propane grill is positioned nearby, allowing for outdoor cooking. The cabin's wooden exterior blends harmoniously with the natural surroundings.
Cabin in Hayward
4.96 out of 5 average rating, 423 reviews

"Das Blockhaus" - cozy, authentic German log cabin

Studio sized log cabin with direct access to Hayward Lake and located just 3.5 miles from the Hatchery Creek Trailhead (Birkie Trail and CAMBA mountain bike trail access at this trailhead). Or you could go hang out at the city beach just half a mile away or launch your boat at the public launch (same place). Also just a short walk to downtown for great coffee, food and drink. Great location! Perfect home base for your Hayward area adventure!! Welcome to the great northwoods - enjoy your stay!!

Top guest favourite
Cabin in Hayward
4.98 out of 5 average rating, 131 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

Guest favourite
A spacious cabin with a distinctive wooden exterior features large triangular windows that provide ample natural light. A deck overlooks the yard, furnished with several red chairs and a grill. Lush green trees surround the property, enhancing its natural setting.
Cabin in South Range
4.85 out of 5 average rating, 150 reviews

Cabin in the Northwoods

Come and enjoy all the Northwoods of Wisconsin has to offer at our beautiful, secluded cabin on our private lake, Long Lake. Enjoy all the amenities we have ,such as, hot tub, canoes, fire pit, and more! Here you will have immediate access to ATV and snowmobile routes, fishing on a private lake, and trails for hiking or hunting. Also conveniently located approximately 15 minutes out side of Superior Wisconsin where you will have access to any needs or amenities along with more sites to see!

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, 102 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.

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
Home in Ironwood
4.99 out of 5 average rating, 298 reviews

"Bakery Bungalow" -Sweet Accommodations & Nature !

Completely remodeled from head to toe! Located within half mile of trail system, 2 miles from historic downtown shops, on the outskirt of town (Ironwood Township=great drinking water) minutes from Big Powderhorn Mountain & Copper Peak, walking distance to Gogebic College & Mount Zion, 17 miles from Lake Superior, large private wooded yard with fire pit in summer, private parking, 1 stall garage if needed in winter. A light Bakery breakfast included with your stay!

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
The cabin features a distinctive A-frame design, showcasing large windows that invite natural light. A spacious deck extends from the front, allowing for outdoor enjoyment, while a chimney suggests a cozy interior. Surrounded by lush greenery, the setting offers a serene atmosphere.
Cabin in Minong
4.87 out of 5 average rating, 150 reviews

Lakefront cabin, pet friendly!

Welcome to Linger Longer Lodge, the perfect year-round escape! This western-facing A-frame cabin offers stunning lake views, especially at sunset, with expansive windows and a large deck that brings the beauty of the outdoors right to your doorstep. Whether you’re planning a cozy couples’ retreat or a fun-filled family getaway, this lakeside cabin has something for everyone, no matter the season.

Popular amenities for Winter holiday rentals

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