Holiday rentals in Winter

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.

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

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!

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.

Trap N' Fish Motel Room 3

Welcome everyone! We have plenty of trailer parking, ride snowmobile and ATV 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.

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

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.

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!

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!

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).

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.

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!