Vacation 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.

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!

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

Hayward Haus, Modern Design w/ Classic Experience

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 This cabin was built in 2021 and host is 13 year "superhost" This is a default "no pets" cabin, however exceptions can be made with permission and a fee. Inquire with host. NEMA 15-40R outlet provided for level 2 EV charging. You bring chord and adapter.

Hemlock Haven Resort 1

Our small resort is reminiscent of the gems that are largely gone in the Northwoods. A quiet, peaceful cabin on the shore of a sportsmen's lake. Barker Lake is a 240 acre lake set in the National Forest. Wildlife is more plentiful than people. Just 25 min southeast of Hayward gets you to the tourist action if you want it. A 14' rowboat comes with the cabin and motor can be rented. The lake is a class A musky lake with smallmouth and various panfish. Kayaks are available free of charge.

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. At 700sq ft, it's intended for two adults, with the option of 2 addtl kids. A queen bed in the loft, in-floor heat, full kitchen, gas fireplace, and washer and dryer. Less than 2 mi from Highway 63, 8 mi from Cable, and 10 mi from Hayward. IG: @Seeleyoaks

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!

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.

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. FYI, We do ask that guests take their trash with them. There is space to park your trailer.

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.

The Happy Porcupine Cottage

Welcome to The Happy Porcupine Cottage, your charming retreat nestled in the heart of Sawyer County, serving as the perfect gateway to the Northwoods experience. Come and experience the Northwoods lifestyle at The Happy Porcupine Cottage – where adventure, relaxation, and natural beauty converge to create unforgettable memories. Book your stay today!