Vacation rentals in Winter

A view from the interior showcases a vibrant garden leading to the Glamping Studio, surrounded by tall trees. Brightly colored flowers bloom in the foreground, while the calm lake is visible in the background under a clear blue sky.

4.95 out of 5 average rating, 118 reviews

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

4.95 out of 5 average rating, 237 reviews

Home in Ladysmith

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

Two hanging chairs are nestled around a tree, suspended from a wooden structure. A circular wooden table rests on the ground, providing a space to gather. The area is surrounded by tall trees and a natural ground covering of pine needles.

4.94 out of 5 average rating, 284 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!

4.94 out of 5 average rating, 32 reviews

A stylish cabin nestled among trees on a wooded lot, visible through a natural pathway lined with autumn foliage. The cabin features a modern metal roof and large windows, reflecting the serene environment of the Wisconsin Northwoods.

Cabin in Winter

Northwoods Cabin

Peaceful retreat in the Wisconsin Northwoods. Well designed and stylish cabin on two wooded acres. Just steps to the Chippewa River. Fully equipped kitchen, 2 full bathrooms and 2 beds on the second floor loft. High speed internet, electric car charger available. ***In winter months, the road/driveway to the cabin are plowed when there is 6+ inches of snow. AWD vehicles are recommended during snow season.*** A shovel is provided in case guests need to shovel path from vehicle to front door.***

An aerial view of the cabin surrounded by dense greenery, showcasing the vibrant forest canopy. The A-frame structure is positioned within a clear space, highlighting the natural setting. A glimpse of rolling hills can be seen in the distance, enhancing the secluded atmosphere.

4.99 out of 5 average rating, 102 reviews

Seeley Oaks A-Frame | Quiet, 40 Acres, Near Trails

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

4.92 out of 5 average rating, 354 reviews

A serene riverfront scene is presented, featuring bare trees against a pastel sky. A small fire pit is surrounded by wooden chairs, inviting relaxation. The gentle reflections of the trees are visible in the calm water, creating a tranquil atmosphere.

Cabin in Ladysmith

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.

4.94 out of 5 average rating, 141 reviews

A serene view of Wilson Lake is captured through a lush frame of greenery. Bright green grass leads up to the water's edge, where trees provide a natural border. The tranquil surface of the lake reflects the surrounding landscape under a clear sky.

Cottage in Phillips

Charming Cottage on Wilson Lake

With a queen bedroom, sitting room/guest room with a futon and cable tv, bathroom with shower, and a complete kitchen, it is a cozy retreat for a couple or single traveler looking for privacy and relaxation. The cottage is located on Wilson Lake, part of Phillips Chain of Lakes. There is a small beach area with a wonderful fire pit with free fire wood, picnic bench and swim raft located on the property. We offer use of our Canoes, Kayaks and a paddle board free of charge to all guests.

4.96 out of 5 average rating, 111 reviews

The exterior of the vacation home features a red wooden facade with multiple windows and a ramp leading up to the entrance. A well-maintained lawn surrounds the property, with a small flower pot placed by the entrance.

Apartment in Winter

Gateway to the Great North Woods by DonBar

Enter the Gateway to the Northwoods with this 3 bedroom, 2 full bath vacation home rental that can sleep 8-10, and comes with a full kitchen, 2 TV's with Netflix & Hulu. It is located on the Tuscobia StateTrail, which is ranked the #1 ATV/UTV trail in the state! It is located within minutes of lakes for fishing and boating, as well as 40 minutes from Hayward and 30 minutes from Ladysmith. A pack and play, highchair, 2 booster seats and board games for children are provided.

Superhost

A living area features natural wood paneling and a soft gray sofa alongside a patterned rug. A wooden chair is positioned nearby, with a side table holding a small decorative item. Large windows invite natural light and offer views of the surrounding trees.

Home in Winter

5 out of 5 average rating, 4 reviews

On the Tuscobia Trail

Right on the Tuscobia Trail, this newly remodeled cabin situated on 30 acres, has all you need for a great stay. 5 min from the Lake Winter boat accessand right across the road from the river. Cabin has circular drive for easy parking of your trailer or boat. Includes central air, WiFi, dishwasher and laundry. 2 covered porches allow you to sit outside and enjoy the wildlife and the Great Northwoods! We do not allow parking on the property prior to 3pm check in.

Superhost

A rustic yurt is surrounded by trees with vibrant autumn leaves. The structure features a circular shape with a green outer cover and a smoke pipe extending from the roof. A deck wraps around the yurt, and a picnic table is visible on the ground amidst fallen leaves.

Yurt in Cable

4.91 out of 5 average rating, 383 reviews

Cable Rustic Yurt

Explore thousands of acres of public forest land and enjoy endless miles of some of the best recreational trails Wisconsin has to offer. Step out of the yurt, located in the middle of Bayfield County Forest land, and right onto CAMBA mountain bike trails and the North End ski trails (which connect to the American Birkebeiner ski trails). This is a rustic, minimally maintained yurt so come prepared to relax, unwind and explore the wonders of the north woods.

5 out of 5 average rating, 18 reviews

Cabin in Winter

Reelaxation Cabin on Lake Winter

Reelax with the whole family at this peaceful reelaxation cabin on Lake Winter. Reel in the 'big one' fishing off the private dock, kayak, paddle board, canoe, or rowboat the lake, and then reelax on the patio with a fire watching the mystic Lake Winter. Reelaxation cabin is a two-bedroom one large bath cozy cabin in Northern Wisconsin with an open floor plan all on one level with no steps.

4.98 out of 5 average rating, 121 reviews

A cozy bedroom features a spacious bed with light bedding draped across it. Mirrored sliding doors reflect the room, and a bedside lamp adds subtle illumination. A window with patterned curtains is partially visible, allowing natural light to enter the space.

Home in Exeland

Cozy Northwoods Getaway

This cozy one-bedroom home 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.

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Popular amenities for Winter vacation rentals

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Free parking on premises

Air conditioning

Other great vacation rentals in Winter

4.99 out of 5 average rating, 76 reviews

A red picnic table, surrounded by lush greenery, is positioned on a stone patio. A potted plant sits atop the table, enhancing the outdoor dining experience by the lakeside. The calm water is visible beyond the trees, creating a serene atmosphere.

Cottage in Tony

Luxe Lakeshore Cottage! *Great Views & Reviews*

MonteRating, 5 stars1 week ago

What a great vacation! Tina’s place is perfect! Her hospitality and helpful information made it so easy and enjoyable. The house is beautiful, the view of the lake, the bird watching and the fire pit is unlike anything I’ve ever seen. Everything was so clean and beautiful. We will definitely be returning.

A fire pit surrounded by several adirondack chairs and metal chairs is set in a grassy area. The back of the cabin is visible, featuring large sliding doors that lead to a spacious deck with outdoor seating and a grill.

4.95 out of 5 average rating, 38 reviews

Osprey Hideaway: Near Hayward, Kayaks and Beach!

CollinRating, 5 stars4 months ago

We stayed here for a snowmobile trip. Stacy was very flexible with rescheduling due to lack of snow for our first trip. There was ample parking for two trucks w/ 30ft trailers. The short drive off the black top as well as direct shore access to the lake was a huge plus. We found plenty of bed space as well as room to cook and congregate after we got home for the night. We will definitely be staying again.

4.98 out of 5 average rating, 53 reviews

A fire pit area is surrounded by smooth stones, with wooden benches placed for seating. In the background, a modern guesthouse with a sloped roof and large outdoor patio is visible, set against a green lawn and trees.

Guesthouse in Ladysmith

The Bunkhouse, a Northwoods Escape

SusanRating, 5 stars1 week ago

My niece and her family stayed in the bunkhouse for a local family event and enjoyed their stay immensely. I communicated with Courtney about possible early check-in and the option to gather around the beautiful firepit in the evening with extended family, and Courtney was gracious to allow and responded quickly to our requests. I highly recommend the Bunkhouse for a quiet and peaceful get-away.

4.93 out of 5 average rating, 41 reviews

Little Sisu - Nordic Hideaway on Silverthorn Lake

KerryRating, 5 stars2 weeks ago

Little Sisu was exactly what we expected! Peaceful, comfy, beautiful surroundings! Jesse was very responsive to any questions and concerns. The cabin had everything we needed and more. We will definitely be back, hopefully in the fall once the sauna is finished!

Superhost

A group of individuals enjoys a sunny day at the lake. A boat is docked at the wooden pier, which features a covered area nearby. A girl in swimwear is seen walking toward the water, while others prepare for water activities such as tubing.

Home in Winter

4.81 out of 5 average rating, 26 reviews

Private lake home on small lake that allows motors

RichardRating, 5 stars9 months ago

such a amazing and beautiful place, the lake is quite and the sunsets are stunning from inside the house or sitting by the fire. This is the second time we have stayed and will definitely be visiting again! Bonus for us that we were able to see the Northern Lights out second night there and it was absolutely breathtaking!!!

5 out of 5 average rating, 16 reviews

A stone woodburning fireplace serves as a focal point, framed by rustic wood paneling. Above the fireplace, a decorative shelf displays candles and autumn-themed decor. The dancing flames create a warm ambiance, complemented by neatly stacked firewood below.

Home in Hayward

Fernwood Forest MTB/Nordic Retreat, Sauna & EV CHG

DuaciRating, 5 stars2 weeks ago

This place was an amazing stay! All pictures and descriptions are exactly what the pictures look like.

4.92 out of 5 average rating, 24 reviews

An open concept living space features high wooden ceilings and natural light streaming through large windows. A comfortable seating area is arranged around a coffee table, and a modern kitchen is positioned along one wall, complete with a kitchen island and appliances. A spiral staircase leads to the loft.

Cabin in Phillips

New waterfront cabin on 18 acres, trail access

ClayRating, 5 stars2 weeks ago

Our family had a great time staying here. Our kids really enjoyed staying in the loft and being able to go on canoe and kayak rides. The property was very peaceful and I wish we could have stayed longer!