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.

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Top Guest favourite
Several black bears are observed climbing trees in a wooded area, surrounded by bare trees and scattered leaves. The setting is tranquil, with soft light illuminating the background, suggesting either early morning or late afternoon.
Guesthouse in Ojibwa
4.96 out of 5 average rating, 75 reviews

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

Guest favourite
Two hanging chairs are suspended from a rustic wooden frame adorned with string lights, creating a warm glow. A fire pit made of stones is positioned below the chairs, surrounded by a wooded setting. A cabin can be seen in the background, softly illuminated through its window.
Cabin in Hayward
4.94 out of 5 average rating, 335 reviews

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!

Top Guest favourite
A wooden dock extends into a calm lake, bordered by lush greenery on both sides. A bench is positioned at the end of the dock, providing a place to relax and enjoy the serene water views. Clear skies reflect gently on the lake's surface.
Cabin in Winter
4.94 out of 5 average rating, 48 reviews

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.

Guest favourite
Chalet in Hayward
4.96 out of 5 average rating, 110 reviews

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

Top Guest favourite
Cabin in Minong
5 out of 5 average rating, 175 reviews

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.

Superhost
A historic log cabin is nestled among lush greenery, standing amidst tall trees with a gentle slope leading to a stone pathway. The cabin features a stone chimney and deep green shutters, harmonizing with the natural surroundings in a peaceful forest setting.
Cabin in Sarona
4.91 out of 5 average rating, 289 reviews

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.

Top Guest favourite
Cabin in Birchwood
4.97 out of 5 average rating, 367 reviews

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.

Guest favourite
Cabin in Winter
4.95 out of 5 average rating, 41 reviews

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.

Guest favourite
Cabin in Birchwood
4.91 out of 5 average rating, 256 reviews

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!

Guest favourite
A set of stone steps leads through lush greenery towards the cabin, framed by trees. The cabin features a deck with seating visible at the top, inviting guests to enjoy the natural surroundings.
Cabin in Stone Lake
4.91 out of 5 average rating, 102 reviews

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!

Guest favourite
Home in Exeland
4.98 out of 5 average rating, 134 reviews

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.

Top Guest favourite
Cabin in Winter
5 out of 5 average rating, 40 reviews

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

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Sawyer County
  5. Winter