Winter Wisconsin Cabin Rentals: Compare the Best Lakeside Stays

By Brian Dohrn | Dohrn Travels | Winter Wisconsin Cabin Rentals

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Winter, Wisconsin is one of the best Northwoods’ spots for a relaxed cabin getaway. The village sits among lakes, rivers, and hundreds of miles of trails—making it a strong base for fishing trips, family gatherings, or quiet weekends away.

Also, I’ve explored the area over the years, and a cabin stay is easily the best way to experience everything Winter, Wisconsin has to offer.

Below, you’ll find a curated list of Winter Wisconsin cabin rentals organized by lake area, so you can choose a stay based on location, amenities, and the type of trip you’re planning.

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Table of Contents

• Quick Overview: Where to Stay in Winter Wisconsin
• Barber Lake Cabin Rental
• Barker Lake Cabin Rentals
• Black Dan Lake Cabin Rentals
• Blaisdell Lake (Chippewa River) Cabin Rentals
• Connors Lake Cabin Rental
• Fishtrap Lake Cabin Getaway
• Hunter Lake Cabin Rental
• Island Lake Cabin Rental
• Lake Winter Cabin Rentals
• Perch Lake Cabin Rentals
• What to Pack for Your Winter Wisconsin Cabin Rentals Trip
• Final Thoughts

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Quick Overview: Where to Stay in Winter Wisconsin

Winter, Wisconsin is a four-season playground that attracts anglers, snowmobilers, paddlers, and anyone who loves the outdoors.

Winter, Wisconsin, sits along the Tuscobia State Trail and near the Chippewa Flowage, offering quick access to lakes, rivers, and hundreds of miles of trails. You’ll find everything from luxury lakeside lodges with hot tubs and fireplaces to budget-friendly cabins perfect for ice-fishing weekends or summer getaways. Each area—from Barker Lake to Lake Winter—offers its own vibe, so you can pick the cabin that matches your kind of Northwoods adventure.

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Barber Lake Winter Wisconsin Cabin Rentals

To begin with, Barber Lake sits just east of Winter, Wisconsin, surrounded by forest and calm water that’s perfect for paddling, fishing, or simply enjoying a quiet sunrise on the dock. It’s one of those Northwoods lakes that feels far from everything yet still close enough to grab dinner in town.

5-Bedroom Barber Lake Cabin (Midrange to Luxury Stay — Winter Wisconsin Cabin Rentals Option)

Price Range: $$$
Best For: Families, groups, and anglers looking for extra space and comfort

If you’re after room to relax without giving up comfort, this 5 Bedroom Barber Lake Cabin is a great pick. The cabin offers direct lake access, a private dock, pontoon included, an outdoor firepit, and plenty of gathering space inside—from a full kitchen to a large family room with lake views. Also, the setting makes it easy to spend your days on the water and your evenings by the fire.

Lastly, travelers appreciate its peaceful setting and easy access to nearby trails and lakes, making it ideal for year-round adventures. The cabin books quickly during peak seasons, so plan ahead if you’re visiting over holidays or summer weekends.

👉 Reserve your stay now on VRBO

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Barker Lake Winter Wisconsin Cabin Rentals

If you like the mix of history, outdoor recreation, and laid-back lake time, Barker Lake is a fantastic area to stay near Winter, Wisconsin. The lake is known for calm waters, easy access to the trails, and the Barker Lake Golf Course—a vintage 1920s course with true Northwoods character. Lastly, you’ll find everything here from rustic cabins to upscale lodges with room to stretch out and unwind.

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Bucktail Lodge (Budget Stay Near Barker Lake)

Price Range: $–$$
Best For: Couples, and small groups looking for a classic Northwoods experience

Set along the shoreline of Barker Lake, Bucktail Lodge is a relaxed resort that captures the spirit of the area perfectly—friendly, low-key, and close to everything that makes Winter, Wisconsin special. The property features three inviting cabin rentals, each with its own character and lake access. Also, guests appreciate the peaceful setting, private docks, and short drive to local trails and dining in Winter.

• Lakeview Cabin – Cozy and comfortable, ideal for couples or small families who want a quiet retreat with lake views.
• Riverview Cabin – Offers space for couples or friends, plus quick access to nearby ATV and snowmobile routes.
• Pineview Cabin – Surrounded by tall pines with a true cabin-in-the-woods feel—great for groups or longer stays.

👉 Reserve your stay now on VRBO

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Legacy Lodge – Historic Prohibition Lodge (Luxury Stay in Winter Wisconsin Cabin Rentals Area)

Price Range: $$$$
Best For: Groups or families seeking an upscale stay with vintage flair

This restored Historic Prohibition Lodge blends the charm of the Prohibition era with the comfort of modern amenities. At this stay, expect spacious bedrooms, a large great room, and a classic stone fireplace perfect for evenings in. Set right on Barker Lake, it’s ideal for reunions, retreats, or travelers wanting both character and comfort in one memorable stay.

👉 Reserve your stay now on VRBO

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Black Dan Lake Cabin Rentals in Winter Wisconsin

Tucked between forest backroads and peaceful shoreline, Black Dan Lake offers a quiet retreat just a few minutes from downtown Winter. Plus, the lake is a local favorite for fishing, kayaking, and unwinding by the water. Also, the lake connects easily to nearby trails and backcountry roads, making it a great base for exploring the Northwoods in any season.

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Newer Luxury Getaway (Luxury Winter Wisconsin Cabin Rental)

Price Range: $$$
Best For: Couples, families, or groups looking for comfort and privacy

If you’re after a cabin that feels fresh and modern without losing that rustic charm, the Newer Luxury Getaway on Black Dan Lake is an excellent choice. The home features floor-to-ceiling windows with lake views, a fully equipped kitchen, and spacious decks for morning coffee or stargazing. Lastly, guests mention the peaceful setting, easy access to the water, and a great layout for families or small groups.

👉 Reserve your stay now on VRBO

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4 Season Family Getaway (Midrange Winter Wisconsin Cabin Stay)

Price Range: $$
Best For: Families, outdoor enthusiasts, and multi-season travelers

The 4 Season Family Getaway delivers that classic Wisconsin cabin experience—cozy enough for winter weekends and roomy enough for summer vacations. Also, with direct lake access, a private dock, and space for campfires or cookouts, it’s built for families who love the outdoors. Its location makes it easy to explore Winter’s trails, nearby lakes, and fishing spots, then come back to a warm, welcoming space.

👉 Reserve your stay now on VRBO

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Blaisdell Lake (Chippewa River) Cabin Rentals in Winter Wisconsin

Set along the Chippewa River near Blaisdell Lake, this area is one of Winter’s most scenic spots for outdoor adventure. In addition, you’ll find calm waters for paddling, great fishing, and easy access to ATV and snowmobile trails that connect through Sawyer County.

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Eagle Lodge Resort & Cabins (Blaisdell Lake — Budget to Midrange Winter Wisconsin Cabin Rentals)

Price Range: $–$$
Best For: Families, anglers, and small groups who want a social, lakeside setting with on-site dining

Eagle Lodge offers a friendly Northwoods resort vibe with comfortable cabins just steps from the water. Also, guests enjoy the on-site bar and grill (known for its Old Fashioneds and pizza), plus direct access to the lake and trails. It’s a great base if you want to fish during the day and relax with food and drinks nearby at night.

The Eagle Lodge Resort offers three main cabins, each with its own layout and charm:

• River Retreat Cabin – Spacious and versatile, perfect for families or groups looking for a full kitchen and lake access.
• Cozy Cabin – Compact and comfortable, ideal for couples or solo travelers who want peace and quiet.
• Large Cabin – Best for bigger groups who want more space to gather indoors and out.

👉 Reserve your stay now on VRBO

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River Retreat (Chippewa River — Midrange Cabin Rental in Winter, Wisconsin)

Price Range: $$
Best For: Couples, small families, paddlers, and nature-lovers who want riverfront privacy

This River Retreat sits right on the Chippewa River with a peaceful back-to-nature feel. It’s great for travelers who want something quiet but still within easy reach of town. Equipped with a full kitchen, Chippewa River access, and cozy spaces that make it easy to unplug and recharge.

👉 Reserve your stay now on VRBO

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Connors Lake Winter Wisconsin Cabin Rentals

Just south of the Flambeau River State Forest, Connors Lake is one of those spots that feels tailor-made for Northwoods relaxation. Also, it’s a clear-water lake surrounded by pine forest, known for calm mornings, sandy beaches, and easy access to hiking, paddling, and snowmobile trails. Whether you’re here for a quiet couple’s weekend or a multi-family getaway, this area delivers both peace and adventure.

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Moxi Lodge at Connors Lake (Midrange to Luxury Winter Wisconsin Cabin Rentals)

Price Range: $$–$$$
Best For: Couples, families, or small groups seeking modern comfort and a lakeside location

Moxi Lodge blends up north comfort with modern style—a favorite among travelers who want something upscale without losing the Northwoods feel. The property offers three unique condo rentals, each with clean design, cozy furnishings, pontoon rental available, and access to lake recreation right outside the door. Also, guests love the location for its proximity to the Flambeau River State Forest, making it a strong pick for four-season adventure.

• The Whitetail – The largest of the 3 condos, offers up north hunting lodge feel.
• The Birchwood – Stylish and comfortable with a bright, open layout ideal for small families or couples.
• The Loft – The most contemporary option, featuring elevated lake views and cozy interior details perfect for a relaxing stay.

👉 Reserve your stay now on VRBO

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Fishtrap Lake Winter Wisconsin Cabin Getaway

Quiet, tree-lined, and ideal for a laid-back escape, Fishtrap Lake sits just northeast of Winter, Wisconsin. The area offers peaceful paddling, great fishing, and plenty of forest roads to explore. It’s a great choice for travelers who want that off-the-grid feel while still being within a short drive of town for supplies or dinner.

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Classic Rustic Lakeside Cabin (Near Fishtrap Lake) (Midrange Winter Wisconsin Cabin Rental)

Price Range: $$
Best For: Couples, small families, or anglers who enjoy simplicity and lakefront access

The Classic Rustic Lakeside Cabin delivers exactly what its name promises—a cozy, comfortable space right on the water. The cabin includes a private dock, screened porch, and easy lake access, it’s ideal for a quiet weekend of fishing, reading, or just watching the sunset over the pines. Inside, the cabin keeps things simple but welcoming, with all the essentials for a relaxed stay.

👉 Reserve your stay now on VRBO

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Hunter Lake Cabin Rentals in Winter Wisconsin

Just north of Winter, Hunter Lake is a peaceful spot surrounded by thick forest and quiet roads—perfect for anyone who enjoys fishing, boating, or simply getting away from it all. It’s a smaller, low-traffic lake that still feels connected to the area’s trail system, making it a solid base for four-season exploring.

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Hunter Lake Lodge (Luxury Winter Wisconsin Cabin Rental)

Price Range: $$$
Best For: Families, groups, or travelers looking for a high-end lakeside escape

The Hunter Lake Lodge combines classic Northwoods character with modern comfort. Expect large windows overlooking the woods, a full kitchen, spacious living areas, hot tub, and outdoor amenities designed for year-round enjoyment. Also, there’s a private dock for summer fishing, a firepit for cool evenings, and plenty of room to gather with friends or family.

Lastly, guests highlight the lodge’s peaceful setting and attention to detail, from cozy furnishings to thoughtful design touches. It’s an ideal pick if you want an upscale stay that still feels connected to the wilderness around Winter, Wisconsin.

👉 Reserve your stay now on VRBO

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Island Lake Winter Wisconsin Cabin Rentals

A short drive northeast of Winter, Wisconsin, Island Lake offers that “tucked-away” Northwoods feel that keeps people coming back year after year. It’s smaller and quieter than some of the area’s larger lakes, making it a great choice for travelers who value peace, wildlife watching, and easy water access without the crowds.

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Cozy Cabin on Island Lake (Budget-Friendly Winter Wisconsin Cabin Rental)

Price Range: $
Best For: Couples, solo travelers, or anyone looking for a simple, lakeside retreat

The Cozy Cabin on Island Lake offers the kind of stay that captures what makes northern Wisconsin special—calm mornings on the dock, quiet evenings by the fire, and just enough comfort to feel at home. Inside, you’ll find a small but efficient space with a kitchen, cozy living area, and lake views that make every sunrise worth getting up for.

Travelers appreciate both its affordability and peaceful location, especially for long weekends or solo getaways. It’s a genuine Northwoods escape where you can unplug and unwind.

👉 Reserve your stay now on VRBO

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Lake Winter Best Cabin Rentals

If you want to stay close to the heart of town while still enjoying that peaceful lakefront vibe, Lake Winter is one of the best spots around. The lake stretches just south of the village, offering direct access to fishing, kayaking, and trail connections right from your doorstep. You can grab groceries or dinner in town within minutes—then be back by the water in time to catch sunset from the dock. It’s a great choice for travelers who want convenience without giving up Northwoods tranquility.

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Luxury Cabin with Hot Tub on Lake Winter (Top Luxury Winter Wisconsin Cabin Rental)

Price Range: $$$$
Best For: Couples or groups who want upscale comfort with lake views

This Luxury Cabin with Hot Tub combines spacious design with lakeside relaxation. Also, guests love the large windows overlooking the water, a private outdoor hot tub, pontoon rental available and the open-concept living area perfect for gatherings. Whether you’re spending the day fishing or snowmobiling, it’s the kind of cabin you’ll actually look forward to coming back to.

👉 Reserve your stay now on VRBO

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Private Island on Lake Winter (Luxury Stay — Unique Winter Wisconsin Cabin Rental)

Price Range: $$$$
Best For: Couples, families, or groups looking for a one-of-a-kind getaway

You don’t see many stays like this—a Private Island on Lake Winter with your own cabin, dock, and 360° views of the water. It’s ideal for travelers who want total privacy and a sense of adventure, yet remain just a short boat ride or paddle from the mainland. Lastly, expect modern amenities, open gathering spaces, pontoon included in your stay and an experience that feels truly unique.

👉 Reserve your stay now on VRBO

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The Lakeside (Midrange Cabin Rental in Winter Wisconsin)

Price Range: $$
Best For: Families or small groups wanting easy access to town and the lake

The Lakeside cabin balances comfort and convenience, with open living spaces, a full kitchen, hot tub, pontoon rental available, and easy water access for boating or fishing. It’s a solid pick for travelers who want a quiet base that’s still close to shops, restaurants, and trails.

👉 Reserve your stay now on VRBO

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The Hideaway on Highland (Midrange Cabin Stay Near Winter, Wisconsin)

Price Range: $$
Best For: Couples or families looking for cozy comfort and wooded privacy

Tucked back from the shoreline, The Hideaway on Highland offers a peaceful, private feel without being far from the action. Also, guests enjoy its warm interior, full kitchen, and outdoor space ideal for campfires or morning coffee in the woods.

👉 Reserve your stay now on VRBO

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Pet-Friendly Lakefront Cabin (Budget Stay for Winter Wisconsin Cabin Rentals)

Price Range: $
Best For: Travelers with pets or anyone looking for an affordable lakeside escape

This Pet Friendly Lakefront Cabin offers a relaxed and welcoming base for your Northwoods stay. It’s simple but scenic—with direct lake access, a small dock, and space for your dog to roam. A great choice for anglers, couples, or solo travelers who prefer to spend more time outdoors than inside.

👉 Reserve your stay now on VRBO

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Perch Lake Cabin Rentals in Winter Wisconsin

Finally, A little off the beaten path, Perch Lake is one of those quiet hideaways that captures everything people love about the Northwoods—calm water, wooded shoreline, and that unmistakable scent of pine in the air. It’s a smaller lake, keeping boat traffic light and mornings peaceful. If you’re after rest, reflection, and easy access to nearby trails and lakes, this area is hard to beat.

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Bobbers Cabin on Perch Lake (Budget Winter Wisconsin Cabin Rental)

Price Range: $
Best For: Solo travelers, couples, or anglers looking for a relaxed retreat

The Bobbers Cabin is as classic as it gets—simple, comfortable, and right on the water. You’ll find all the basics here: a cozy interior, outdoor seating, and easy lake access for fishing or kayaking. Lastly, it’s a no-fuss option that keeps the focus where it should be—on enjoying the quiet.

👉 Reserve your stay now on VRBO

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Bears Den (Midrange Stay for Winter Wisconsin Cabin Rentals)

Price Range: $$
Best For: Couples or small families who want modern comfort in a peaceful setting

The Bears Den offers a step up in space and amenities while keeping the rustic Northwoods feel. Inside, you’ll find a full kitchen, comfortable living area, and outdoor space designed for campfires and conversation. It’s perfect for anyone who wants a balance of comfort and simplicity surrounded by nature.

👉 Reserve your stay now on VRBO

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What to Pack for Your Winter Wisconsin Cabin Rentals Trip

Traveling to Winter, Wisconsin means packing for real Northwoods conditions — cool mornings, windy lakes, muddy trails, and days that jump between fishing, hiking, and exploring small-town backroads. Layers and versatility go a long way here, and bringing the right gear saves you from mid-trip store runs or soggy days on the trail.

Here’s a practical, experience-tested list of what actually helps when you’re exploring the Winter, Wisconsin area:

• Polarized Sunglasses — cut the glare off clear lakes and help you spot wildlife along forest roads.
• Short-Sleeve or Long-Sleeve Fishing Shirt — breathable, quick-drying, and great for sunny afternoons on the water.
• Crocs — easy “in and out” shoes for campfires, fishing trips, or early-morning coffee on the deck.
• Yeti Rambler Tumbler — keeps coffee hot for sunrise drives or long mornings by the lake.
• First-Aid Kit — helpful for cuts, campfire burns, or minor trail scratches.
• Hard-Sided Cooler — sturdy enough for extra seating and keeps drinks cold on long outings.
• Knit Cuffed Beanie — perfect for crisp mornings or breezy lake evenings.
• Hoodie — that dependable mid-layer you’ll reach for every night.
• Uno Cards — simple cabin fun for rainy afternoons or unplugged evenings.
• Headlamp — great for firewood runs, late-night walks, or navigating unlit cabin paths.
• Picaridin Insect Repellent — clutch in mosquito season, especially around lakes and marsh edges.
• Ugly Stik Spinning Combo Rod and Northland Gum-Ball Jigs  — dependable for casting from lake docks for panfish and walleyes.
• ATV / UTV GPS — keeps you oriented on Sawyer County trail networks.
• Camping Chair — perfect for dock fishing, campfires, or relaxing by the water.
• Kayak — ideal for paddles on Connors Lake, Chippewa River, or Lake Winter.
• Inflatable River Tube — fun for summer floats along the Flambeau or Chippewa River.

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Final Thoughts on Booking Winter Wisconsin Cabin Rentals

No matter which lake you choose, Winter Wisconsin cabin rentals make it easy to experience the best of the Northwoods—peaceful lakes, endless trails, and a community that still moves at a slower, friendlier pace. Each area offers its own version of adventure, from paddling on the Chippewa River to snowmobiling through fresh powder on the Tuscobia Trail.

If you’re planning a full getaway, don’t miss my guide to Things to Do in Winter, Wisconsin (2025) —it’s packed with local insight on where to explore, eat, and unwind while you’re here.

So pick your cabin, pack your gear, and get ready for a little peace and quiet surrounded by pine trees and good company.

Adventure Awaits. Book It!