Holiday rentals in Winter

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

Lake Front Cabin with Arcade, Connects with Trails

Escape to Callahan's Shore Thing, a rustic, modern, cozy cabin nestled on the water's edge of a gorgeous 2 acre lot with 100+ ft of lake frontage--minutes from downtown Hayward. You won't find a cabin this close to the water, we promise! Enjoy morning coffee on the spacious, multi-level deck, spend your days kayaking or fishing off our private pier, retreat to the seasonal bunkhouse to relax, or head out to our Musky Lounge to have a beer and play some cards with friends. This place has it all!

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

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.

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

THE SUNROOM SUITE @Loon Loon Lake Guesthouse

Only 10 minutes and a world away from Hayward, the stylishly appointed SUNROOM SUITE is part of Loon Lake Guesthouse. Take in the view of gardens, tall pines and glimmering Loon Lake through windows and skylights that overlook this picturesque setting. Summertime brings swimming, canoeing, bird watching and walking the loop. Venture out for some day tripping or work remotely with Starlink WiFi. And be sure to make time for luxuriating in the soaking tub. Life is sweet in The Sunroom.

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

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.

Fancy Fireflies-Charming studio Cabin in Hayward

Surrounded by trees, settled right on Lake Hayward sits this charming & cozy cabin in a little cabin community less than half a mile from downtown Hayward. Launch your canoe just steps from the cabin's entrance, bike into town for lunch, or go hiking or skiing on the nearby trails, this cabin is nestled in the perfect location! This is a cozy, studio size cabin with one queen bed, a bathroom, a kitchenette with a mini-fridge, microwave, Keurig coffeemaker & outdoor grill.

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!

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.

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.