
Holiday houses in Winter
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Top-rated holiday rentals in Winter
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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.

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

Pets Welcome - RV/EV Friendly - Minong Flowage
*NEW March 2024* RV/ EV Charger Receptacles- 50 AMP Nema 14-50R and 30 AMP NEMA TT-30R - RV Connection **NEW April 2024** Playground Located on the Kings CT peninsula of the very popular 1500 acre Minong Flowage big enough to quench virtually any type of outdoor sport that interests you year 'round. The property is surrounded by 3 acres of property which provides privacy for bbq'ing, yards games, kids playground, and a custom stone fire pit. Public boat landing down the street.

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.

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. (The cabin has an open floor plan, so no actual bedrooms, sleeping spaces in the loft are separated by a closet wall). 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.

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.

Lakefront Sunset Cabin w/Boats, Spa, FirePit & BBQ
Extraordinary lakefront home, private lake access! Bring your own boat, or use one of ours! Relax on the screened-in patio while watching lake wildlife. BBQ on our charcoal grill, then enjoy a game of cornhole or SpikeBall near the lakeside firepit. Cast a line for great fishing right out front, or push the boats in the water and explore Birch Lake. After a full day, wind down in the hot tub - which is available for you to enjoy year round!

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!

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!
Popular amenities for Winter holiday rentals
Other great holiday rentals in Winter

Winding Creek Cabin - next to the Ice Age Trail!

Hayward Family Cabin w/ Pontoon Rental Available

Lakeview Lodge

JHGetaways

Cabin in the Pines

Cozy *TreeTop Nature* stay

Cabin on Sawyer Creek Rd.

Gateway to the Great North Woods by DonBar
Destinations to explore
- Upper Peninsula Holiday rentals
- Platteville Holiday rentals
- Minneapolis Holiday rentals
- Milwaukee Holiday rentals
- Wisconsin River Holiday rentals
- Traverse City Holiday rentals
- Wisconsin Dells Holiday rentals
- Madison Holiday rentals
- Twin Cities Holiday rentals
- Thunder Bay Holiday rentals
- Lake Geneva Holiday rentals
- Duluth Holiday rentals





