
Vacation rentals in Winter
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Winter
Guests agree: these stays are highly rated for location, cleanliness, and more.

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

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

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!

Vintage 1940's Hayward Cabin!
Gorgeous 1940's cabin renovated inside and out in 2018! Nestled in the Northwoods, this home has a full kitchen w/ all amenities, cable TV/Wifi, large deck w/ table & chairs, charcoal grill and fire pit! Surrounded by premier lakes with 4 nearby boat landings to both Lac Courte Oreilles and Grinstone. Seasonal view of Lac Courte Oreilles- but no water access granted with rental. Only 15 minutes to downtown Hayward or Stone Lake! Enjoy the pleasure of a home for the price of a hotel room!

Seeley Oaks A-Frame | Secluded Retreat on 40 Acres
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

Cabin in the Northwoods
Come and enjoy all the Northwoods of Wisconsin has to offer at our beautiful, secluded cabin on our private lake, Long Lake. Enjoy all the amenities we have ,such as, hot tub, canoes, fire pit, and more! Here you will have immediate access to ATV and snowmobile routes, fishing on a private lake, and trails for hiking or hunting. Also conveniently located approximately 15 minutes out side of Superior Wisconsin where you will have access to any needs or amenities along with more sites to see!

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.

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

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.

"Bakery Bungalow" -Sweet Accommodations & Nature !
Completely remodeled from head to toe! Located within half mile of trail system, 2 miles from historic downtown shops, on the outskirt of town (Ironwood Township=great drinking water) minutes from Big Powderhorn Mountain & Copper Peak, walking distance to Gogebic College & Mount Zion, 17 miles from Lake Superior, large private wooded yard with fire pit in summer, private parking, 1 stall garage if needed in winter. A light Bakery breakfast included with your stay!

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!

Cozy Fireplace in a Northwoods Tiny House
Deer Haven is a tiny house (192 sq feet) located in my backyard, overlooking acres of woodland. The space is small and simple. Get to the queen bed in the sleeping loft by climbing the ladder. Bathroom has a toilet and stock tank shower. The kitchen has basic amenities - fridge, microwave, hot plate, griddle, dishes, etc. Best spot in the house is on the couch, where you can see the fireplace and the gorgeous woods out the patio door.
Popular amenities for Winter vacation rentals
Other great vacation rentals in Winter

Hidden Bay: Modern. Wild. Clean. Sunset Views.

The Bunkhouse, cozy Northwoods studio escape!

Chalet Blu-Hot Tub/SPA shower next to Christie Mt

Lincoln Log Cabin perched along the Jump River.

Pet-Friendly Lakeside Chalet with Sauna!

Up North Rentalz, LLC

Connor’s Lake, sleeps 6, Near UTV trails, WiFi

The Mill Pond Apartment - .5mi to Downtown Hayward
All about Winter
Winter bills itself one of Wisconsin’s largest towns, but it’s referring to the size of the township, not the population — its 900-some residents are scattered across 285 square miles. Winter draws visitors from all over the Midwest because it’s a rustic and gorgeous part of the Northwoods, free of ticky-tacky tourist attractions and vacation traffic. Vast expanses of forest cup the town around its eastern side, and to the northwest is the sprawling Chippewa Flowage. Canoe on the Flambeau River’s whitewaters. Hike through the Chequamegon National Forest. Cross-country ski along the Flambeau Hills Trail. Fish in the Chippewa River or one of the dozen or so lakes that the state keeps stocked with walleye, muskie, bass, and panfish. Your trip to Winter can be as relaxing or exciting as you choose. And isn’t that the reason we take vacations?
What are the top things to do in Winter?
Tuscobia State Trail
Fans of off-road driving love this corner of the Northwoods for the plethora of well-groomed, scenic ATV trails. And one of Wisconsin’s best is the 62-mile Tuscobia State Trail, which passes through Winter. If you head northeast from town, you’ll hit a spur trail that takes you through the Flambeau River State Forest or, further along, you can link up with the Chequamegon-Nicolet National Forest routes. To the west, you’ll follow the curves and rapids of the Chippewa River before delving into lush woodlands. In winter, snowmobiles take over the trail.
Chippewa Flowage
The damming of the Chippewa River in 1923 created this spectacular, multi-tendriled artificial lake, which has 15,000 acres of water and more than 200 miles of shoreline. Fishing is the main attraction here — anglers particularly love scouting out the moving bogs where walleye, crappie, and muskie hang out — and in the winter, guides help visitors find the right spot on the ice. There are dozens of spots around the lake to slip a canoe or kayak into the water, too. Bring your binoculars for birding — or for getting a closer look at the deer, bears, and otters who make their home here, too.
Chequamegon-Nicolet National Forest
The eastern Chequamegon half of Wisconsin’s largest swath of federally protected land starts about 10 miles north of Winter and stretches out over 865,000 acres of dense maple, oak, pine, and spruce — most of it second-growth forest restored 90 years ago after the area was logged. Here you’ll find hundreds of miles of trails for hiking and cross-country skiing, crystal-clear glacial lakes for swimming and fishing in, streams for navigating in a canoe, and well-groomed routes for exploring on ATV or snowmobile.
Destinations to explore
- Upper Peninsula Vacation rentals
- Platteville Vacation rentals
- Minneapolis Vacation rentals
- Wisconsin River Vacation rentals
- Milwaukee Vacation rentals
- Twin Cities Vacation rentals
- Madison Vacation rentals
- Traverse City Vacation rentals
- Wisconsin Dells Vacation rentals
- Thunder Bay Vacation rentals
- Lake Geneva Vacation rentals
- Duluth Vacation rentals




