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
Cabin in Hayward
4.96 out of 5 average rating, 102 reviews

Cozy Trailside Nordic Forest Cottage

Welcome to the Trailside Gökotta Forest Cottage: a modern, minimalist and serene nature cabin on the Birkie Trail system. Gökotta means 'to get up early to listen to sounds of birds and the forest'. Located right on Birkie Ridge Trailhead with close access to vast CAMBA trails, this is a nature escape for outdoor enthusiasts who love to bike, ski, hike, and bird watch. Enjoy ski-in ski-out to groomed trails, bike-in bike-out right onto trails, then cozy up by the woodstove or fire-pit at night.

Top Guest favourite
Several black bears are observed climbing trees in a wooded area, surrounded by bare trees and scattered leaves. The setting is tranquil, with soft light illuminating the background, suggesting either early morning or late afternoon.
Guesthouse in Ojibwa
4.96 out of 5 average rating, 75 reviews

Two bedroom cottage w/ access 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 recreational vehicles. Ride Tuscobia trail system with endless trails to neighboring towns/villages such as Winter, Radisson, Birchwood SxS, UTV, WHLR 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

Top Guest favourite
A wooden dock extends into a calm lake, bordered by lush greenery on both sides. A bench is positioned at the end of the dock, providing a place to relax and enjoy the serene water views. Clear skies reflect gently on the lake's surface.
Cabin in Winter
4.94 out of 5 average rating, 48 reviews

Connor’s Lake, sleeps 6, Near UTV trails, WiFi

Take a break and unwind at this peaceful oasis on Connor’s Lake. 420 acre lake with excellent fishing. Quiet, beautiful lake front with gorgeous sunrises. Central air. 2 BR, one bath, fully stocked kitchen, washer/dryer, gas grill. 2 full bedrooms each with a queen size bed. 2 fold out futons in living room. Fire pit and firewood. 1/2 mile from UTV, snowmobile and hiking. Cocktail lounge on the lake. 2 restaurants nearby. No smoking/ pets. Newly remodeled guest house with bar, TV, futon.

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, 110 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
Cabin in Winter
4.86 out of 5 average rating, 7 reviews

Bluegill Lake Rustic Cabin

Bluegill Cabin is the quintessential northern Wisconsin cabin; cozy, private, with lots of rustic charm. Situated on nearly 2 acres of land and over 100 feet of lake frontage, there is something for every outdoor enthusiast! The lake is 26 acres of spring-fed clear water; perfect for fishing, swimming, kayaking, floating, or watching the loons, turtles, and otters. This is a no-wake lake and motorized watercraft are prohibited, keeping our water and shoreline clean and pristine!

Superhost
A historic log cabin is nestled among lush greenery, standing amidst tall trees with a gentle slope leading to a stone pathway. The cabin features a stone chimney and deep green shutters, harmonizing with the natural surroundings in a peaceful forest setting.
Cabin in Sarona
4.91 out of 5 average rating, 289 reviews

Hunt Hill's Rustic Log Cabin

Welcome to Hunt Hill Nature Center! We are a public, non-profit learning center and nature sanctuary. Our historic Log Cabin is nearly a century old and offers a peaceful retreat in the woods. All the furniture was updated in 2018. The Log Cabin is located just outside of the main camp, settled on top of a hill overlooking pristine forest habitat. Nearby towns offer additional entertainment or relax in our quiet setting while reading a good book in front of the stone fireplace.

Guest favourite
Home in Winter
4.91 out of 5 average rating, 32 reviews

The Lakeside: Hot Tub Ice Fishing Snowmobile Trail

Discover "The Lakeside" on Lake Winter! Perfect for 8 guests across 4 bedrooms, this retreat is your ideal escape. Unwind in the hot tub, fish from the dock, or lounge on the wrap-around deck. With direct access to the Tuscobia Trail, it's a haven for outdoor enthusiasts. Pontoon rental available for exploring the waters. Spacious interiors and ample parking ensure a comfortable stay for families and friends. Book now for an unforgettable lakeside getaway in Wisconsin!

Top Guest favourite
A cozy living area is highlighted by a stone fireplace with a wooden mantle, complemented by rustic wood paneling and a vaulted ceiling. Comfortable seating options, including a plush sofa and chairs, surround a wooden coffee table, inviting relaxation.
Cabin in Winter
4.97 out of 5 average rating, 58 reviews

Bobbers Cabin on Private Lake

This cozy cabin is tucked away in the woods and offers an easy approach and spectacular lake views of Perch Lake in Winter, Wisconsin. It is a modern renovation of a summer fishing cabin, with its wood-clad walls, exposed beams, and large windows that deliver amazing sunrises. While it maintains the original footprint and some of the rustic charm, it offers many modern comforts and amenities. Cabin sleeps 4. Children and dogs are welcome (limit 2 dogs - $25 per dog).

Guest favourite
The exterior of the cabin presents a wide deck adorned with seating areas and potted plants. Large windows reflect natural light, enhancing the views of the surrounding greenery. A grassy area borders the deck, contributing to the inviting outdoor setting.
Cabin in Winter
4.95 out of 5 average rating, 41 reviews

The Hideaway on Highland

Welcome to our newly constructed cabin. Our cabin features an open concept design, with tons of windows and natural light flooding the space. Whether you're snuggled up on the couch or cooking in the kitchen, you'll feel right at home. The basement has a game room, complete with an air hockey table, foosball table. After a long day of hiking, biking, or hanging out on the water unwind on the deck or catch your favorite movie on the flat-screen TV.

Guest favourite
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, 6 reviews

Trap N' Fish Motel Room 9

Welcome everyone! We have plenty of trailer parking, ride snowmobile and ATV 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
A scenic outdoor seating area features four red adirondack chairs arranged around a stone fire pit. Tall trees provide shade, while the tranquil water of Slim Lake is visible beyond the clearing, with a dock and kayaks nearby.
Cabin in Stone Lake
4.92 out of 5 average rating, 100 reviews

Slice of Paradise on Slim Lake

This cozy cabin in Stone Lake provides a true sense of the tranquil life in the Northwoods and is the perfect spot for your getaway! The cabin faces West on the charming and spring fed Slim Lake (great for swimming, recreation, and fishing). You can enjoy a morning coffee on either the deck or beautiful three season porch overlooking the water. It is a perfect spot for families and friends to make great memories at any time of the year!

Guest favourite
Home in Exeland
4.98 out of 5 average rating, 134 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