Holiday rentals in Winter

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Top-rated holiday rentals in Winter

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Top guest favourite
A field stone fireplace serves as a central feature against walls constructed with natural birch logs. A stone mantel provides a surface for decorative items and creates a cozy focal point. Soft lighting from above enhances the inviting atmosphere of the room.
Cottage in Rice Lake
4.98 out of 5 average rating, 125 reviews

Stonehaven - The Birchview Suite Lower Level

The Birchview Suite lower level duplex is totally closed off from guests in upper level. It features two french doors that lead out to the large flagstone patio area, which is the main entrance. There's a full kitchen for you to prepare meals. We have a private dock 1/4 mile from the cottage and offer complementary use of kayaks, row boats, and canoes! We also have a pontoon for rent. Plenty of hiking and biking opportunities can be found on and off the resort. State Trails are also nearby.

Top guest favourite
A rustic cabin is nestled among lush greenery, showcasing a wooden exterior and a steeply angled roof. The cabin features two skylights on the upper level and a welcoming front porch, surrounded by well-maintained landscaping and natural foliage.
Cabin in Ladysmith
4.93 out of 5 average rating, 376 reviews

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.

Top guest favourite
An outdoor seating area showcases comfortable green adirondack chairs arranged around a stone firepit, with a fire actively burning. A wooden structure is visible in the background, surrounded by lush greenery and tall trees, creating a serene natural setting.
Chalet in Hayward
4.96 out of 5 average rating, 106 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

Guest favourite
Yurt in Cable
4.97 out of 5 average rating, 171 reviews

Perry Pines Yurt | Lakefront - Near CAMBA & Birkie

The Perry Pines Yurt is a 4-season yurt on Perry Lake less than 2 miles from Cable. With quick access to CAMBA mountain bike trails (4 miles to the North End Trailhead), the Birkie Start Area (5 miles), and on an ATV route, it's a great basecamp for your outdoor activities. Sit on the deck and listen to the loons in the summer or warm up next to the woodstove or in the barrel sauna in the winter. Enjoy a full kitchen, bathroom w/shower, lake views, and a fun little unique cabin option!

Top guest favourite
A modern cabin is set among tall trees, featuring a spacious wooden deck with stairs leading up to it. Large windows offer views into the interior, while warm lighting creates a welcoming atmosphere as dusk approaches.
Cabin in Park Falls
4.9 out of 5 average rating, 101 reviews

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.

Superhost
The exterior of a recently remodeled house is shown, featuring a stone chimney and a metal roof. Lush green grass surrounds the house, and trees are visible in the background. A welcoming front porch is framed by a large window.
Home in Loretta
4.86 out of 5 average rating, 7 reviews

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.

Guest favourite
Home in Winter
4.91 out of 5 average rating, 32 reviews

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!

Top guest favourite
A cozy living area is highlighted by a stone fireplace with a wooden mantle, complemented by rustic wood paneling and a vaulted ceiling. Comfortable seating options, including a plush sofa and chairs, surround a wooden coffee table, inviting relaxation.
Cabin in Winter
4.96 out of 5 average rating, 55 reviews

Bobbers Cabin on Private Lake

This cozy cabin is tucked away in the woods and offers an easy approach and spectacular lake views of Perch Lake in Winter, Wisconsin. It is a modern renovation of a summer fishing cabin, with its wood-clad walls, exposed beams, and large windows that deliver amazing sunrises. While it maintains the original footprint and some of the rustic charm, it offers many modern comforts and amenities. Cabin sleeps 4. Children and dogs are welcome (limit 2 dogs - $25 per dog).

Guest favourite
The exterior of the cabin presents a wide deck adorned with seating areas and potted plants. Large windows reflect natural light, enhancing the views of the surrounding greenery. A grassy area borders the deck, contributing to the inviting outdoor setting.
Cabin in Winter
4.95 out of 5 average rating, 40 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.

Top guest favourite
The peaceful cabin is nestled on a spacious lawn surrounded by trees displaying autumn colors. A covered patio with seating options faces the yard, and a charcoal grill is visible nearby. The structure features a simple, rustic design under a clear blue sky.
Cabin in Winter
5 out of 5 average rating, 33 reviews

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.

Guest favourite
The living area features a plush gray sofa with a light throw draped over it, complemented by a wooden armchair. A small dining table with four chairs is visible, while natural light filters through sheer curtains covering a nearby window. A television is mounted on the wall opposite the sofa.
Home in Exeland
4.98 out of 5 average rating, 132 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
The kitchen area features light wooden cabinetry above a spacious countertop. A double sink is positioned below a window, allowing natural light to illuminate the workspace. Essential appliances, including a coffee maker and stove, are neatly arranged, contributing to a functional cooking environment.
Cabin in Winter
5 out of 5 average rating, 36 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