Holiday rentals 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
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.

Top guest favourite
A private cottage is set amidst a snowy landscape, with pine trees surrounding the property. Two chairs are positioned on the front porch, providing a serene view of the winter scenery. The gravel driveway is flanked by untouched snow, leading to the cottage entrance.
Guest house in Ojibwa
4.96 out of 5 average rating, 73 reviews

Quaint 2 bedroom cottage, snowmobiling to trails!

Welcome! Come stay at this quiet retreat or headquarters for your weekend of trail riding! Private cottage with plenty of parking space for your trailers and snowmobiles. Ride Tuscobia trail system with endless trails to neighboring towns/villages such as Winter, Radisson, Birchwood Snowmobile trl riding, great outdoors! Enjoy the outdoors and stay in the WI Northwoods. Several dining options with great fish fries. Hayward is just 30 miles west and Ladysmith is 23 miles south

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.

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.

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!

Top guest favourite
The living area features a plush gray sofa with a light throw draped over it, complemented by a wooden armchair. A small dining table with four chairs is visible, while natural light filters through sheer curtains covering a nearby window. A television is mounted on the wall opposite the sofa.
Home in Exeland
4.98 out of 5 average rating, 130 reviews

Cozy Northwoods Getaway

Our cozy, updated, one-bedroom cottage in Northwestern Wisconsin is the perfect place from which to launch your Northwoods adventures. It is located very close to several lakes and rivers which are great for boating, kayaking, and fishing. The home is within a few miles from several highways that lead to all the adventures that northwestern Wisconsin has to offer.

Popular amenities for Winter holiday rentals

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