
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.

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

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

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. 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

Cozy 2 bedroom cabin on the water - must see!!
Enjoy a quiet, relaxing week in the north woods of Hayward, WI! Our 2 bedroom, 2 bath cabin sleeps six comfortably (2 queen beds and a futon). Cabin is two levels and 1500 square ft. The cabin is located on the Namekagon River with direct access to Hayward Lake and the public boat launch just a few hundred feet away. You really get the best of both worlds here as the cabin is tucked away in a private, wooded area but is also walking distance to downtown Hayward and other attractions!!

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.

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.

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.

Lakefront cabin, pet friendly!
Welcome to Linger Longer Lodge, the perfect year-round escape! This western-facing A-frame cabin offers stunning lake views, especially at sunset, with expansive windows and a large deck that brings the beauty of the outdoors right to your doorstep. Whether you’re planning a cozy couples’ retreat or a fun-filled family getaway, this lakeside cabin has something for everyone, no matter the season.

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.

Birchwood Blue Cabin- Come to the Wild Blue
Experience the forest of NW Wisconsin at our cozy cabin situated on 40 acres of forest with 2 meadows & a small stream. Hike through gently rolling hills of oak, maple & evergreen stands... or just sit still and let nature rejuvenate you. Unplug and Unwind. (We are dog friendly &welcome well behaved dogs, let us know if you plan to bring your dog/s.
Popular amenities for Winter holiday rentals
Other great holiday rentals in Winter

Timber Pines

Luxurious Lakehouse | Snowmobiler's Paradise

Little Sisu - Nordic Hideaway on Silverthorn Lake

Cabin in the Pines

Gateway to the Great North Woods by DonBar

Dam Cabin on Dam Road

Northwoods Cabin

Hunt Hill's Rustic Log Cabin
Destinations to explore
- Upper Peninsula Holiday rentals
- Platteville Holiday rentals
- Minneapolis Holiday rentals
- Wisconsin River Holiday rentals
- Milwaukee Holiday rentals
- Twin Cities Holiday rentals
- Traverse City Holiday rentals
- Madison Holiday rentals
- Wisconsin Dells Holiday rentals
- Thunder Bay Holiday rentals
- Lake Geneva Holiday rentals
- Duluth Holiday rentals




