Holiday houses in Winter

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Top-rated holiday rentals in Winter

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

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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, 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

Top Guest favourite
Home in Ladysmith
4.95 out of 5 average rating, 260 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
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, 326 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
A charming cabin, surrounded by vibrant green grass and shaded by tall trees, is depicted. The cabin features a dark exterior complemented by large windows, allowing natural light to fill the interior. A spacious deck is visible, enhancing the outdoor living space.
Cabin in Hayward
4.98 out of 5 average rating, 201 reviews

Vintage 1940's Hayward Cabin!

Gorgeous 1940's cabin renovated inside and out in 2018! Nestled in the Northwoods, this home has a full kitchen w/ all amenities, cable TV/Wifi, large deck w/ table & chairs, charcoal grill and fire pit! Surrounded by premier lakes with 4 nearby boat landings to both Lac Courte Oreilles and Grinstone. Seasonal view of Lac Courte Oreilles- but no water access granted with rental. Only 15 minutes to downtown Hayward or Stone Lake! Enjoy the pleasure of a home for the price of a hotel room!

Top Guest favourite
Cabin in Hayward
4.99 out of 5 average rating, 134 reviews

Seeley Oaks A-Frame | Secluded Retreat on 40 Acres

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, 153 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
Chalet in Hayward
4.96 out of 5 average rating, 105 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
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
The exterior of a rustic home features a screened-in patio shaded by trees. A charcoal grill is positioned nearby, with cornhole boards available on a grassy lawn. A small detached building is visible in the background, surrounded by a natural landscape.
Cabin in Birchwood
4.92 out of 5 average rating, 232 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!

Superhost
A rustic bedroom features a log bed with themed bedding showcasing bears. Two bedside tables hold lamps, adding ambiance. A green armchair is positioned nearby, creating a welcoming reading nook. Natural light floods the space, highlighting the warm wooden accents and neutral grey walls.
Apartment in Winter
5 out of 5 average rating, 3 reviews

Trap N' Fish Motel Room 9

Welcome snowmobilers! We have plenty of trailer parking, ride snowmobile right up to your door, trail 5 just seconds away, and hot food at Trap N Fish Lodge across the road! Ask us how you can rent the entire motel for large groups for a discounted rate! Room 9 comfortably sleeps 4. 1 bedroom with full kitchen, and bathroom. Soap and towels included. 1 Bedroom includes 2 twin beds. Living Room contains a queen bed. Roku and Wifi included.

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
4.88 out of 5 average rating, 153 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