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Holiday rentals in Winter

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Winter

Guests agree: these stays are highly rated for location, cleanliness, and more.

Cabin in Winter
Paradise Pines
Quiet, cozy north woods cabin located about 45 minutes southeast of Hayward, WI. Perfect place to escape the grind of everyday life! Fishing, hiking, ATV/snowmobile trails accessible within a mile of the cabin, cross country skiing, golf, and hunting close by. Property borders thousands of acres of public hunting land. Hayward area amenities also include mini golf, many small shops and candy/ice cream, and freshwater fishing hall of fame. Please note: pets are not allowed inside.
$130 SGD per night
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Guest house in Ojibwa
Snowmobile enthusiasts! Cottage on private road.
Private cottage with plenty of parking space for your snowmobiles! Ride from cottage to the Tuscobia trail system providing endless trails to neighboring towns/villages such as Winter, Radisson, Birchwood Direct access to Tuscobia trail. Christie Mountain is about a 45 minute drive. Snowshoeing at Ojibwa park or right on the property, with a 3/4 mile loop through the woods. The upstairs garage has a pool table, foosball, darts, direct tv w/ NFL Sunday package
$129 SGD per night
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Home in Winter
Bungalow Trail
Come stay in this 2 bedroom modern bungalow that puts you next to all the amenities that the Northwoods has to offer. Across the road is the State Tuscobia ATV and Snowmobile trail. Down the road is a class A Musky Lake and just a block away is the popular Patti's on 70 Bar and Grille. If your in the mood for a drive, within 30-40 miles you can enjoy wineries, casinos, and other tourist destinations
$145 SGD per night
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Other great holiday rentals in Winter

Cabin in Hayward
Hayward Haus, Modern Design w/ Classic Experience
$318 SGD per night
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Cabin in Winter
Loons Nest Cabin on Private Lake
$209 SGD per night
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Rental unit in Winter
Gateway to the Great North Woods by DonBar
$149 SGD per night
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Cabin in Ojibwa
Available Christmas! Secluded Riverview Cabin
$165 SGD per night
Home in Winter
Private lake home on small lake that allows motors
$263 SGD per night
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Cabin in Hayward
Private Home on Upper Twin Lake, Close to Trails
$181 SGD per night
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Cabin in Hayward
Osprey Cabin
$109 SGD per night
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Cabin in Ladysmith
Flaming Torch Lodge
$150 SGD per night
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Cabin in Hayward
Your Northwoods Escape!
$207 SGD per night
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Cabin in Hayward
Hayward Four Season Moose Lake Getaway
$199 SGD per night
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Cabin in Winter
Hemlock Haven Resort 1
$217 SGD per night
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Cabin in Hayward
Aspen Cabin-Lost Land Lake Waterfront Getaway
$183 SGD per night
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  1. Airbnb
  2. United States
  3. Wisconsin
  4. Sawyer County
  5. Winter