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Holiday rentals in Winter

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Top-rated holiday rentals in Winter

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

Cabin in Hayward
Hayward Haus, Modern Design w/ Classic Experience
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. A heavy emphasis has been placed on aesthetics, comfort, usability of space, and privacy. Cabin is brand new as of August 2021. Host is 13 year "superhost" October-May features "length of stay" discounts, 10% for 4 nights, 12.5% for 5, 15% for 7+
₹16,180 per night
SUPERHOST
Guest house in Ojibwa
Adorable wooded Guest Cottage on private road.
Relax just the two of you or with the whole family at this peaceful cottage. Enjoy the firepit, wildlife, go for a walk, read a good book or fire up the grill! Tuscobia trail is about 1 mile down the road, you can ride straight from the cottage with your side by side or ATVs! Enjoy several dining options within 5 miles or adventure out further! Cooler weather means it getting close to hitting those ski and snowmobile trails! Enjoy the Tuscobia trail and Christie Mountain (short drive).
₹6,992 per night
SUPERHOST
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.
₹8,049 per night
SUPERHOST

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Other great holiday rentals in Winter

Guest house in Ojibwa
Club Suite Recreational Retreat
₹9,757 per night
SUPERHOST
Cabin in Winter
Connors Lake Cabin
₹24,392 per night
Home in Winter
Connors Lake WI - Chalet and Bunkhouse
₹60,979 per night
Apartment in Winter
"The Loft"... Upscale while still Up North!
₹16,261 per night
SUPERHOST
Cabin in Winter
Loons Nest Cabin on Private Lake
₹12,928 per night
SUPERHOST
Home in Winter
Private lake home on small lake that allows motors
₹14,228 per night
SUPERHOST
Cabin in Winter
Hemlock Haven Resort 1
₹13,415 per night
SUPERHOST
Home in Exeland
Cozy Northwoods Getaway
₹5,558 per night
SUPERHOST
Cabin in Hayward
Country Cabin on the Chippewa Flowage, Hayward WI
₹7,971 per night
Cabin in Ojibwa
Available Christmas & Birkie! Riverview Cabin
₹8,595 per night
Home in Exeland
Private 2 Bedroom Home on 10 Acres
₹7,236 per night
Cabin in Hayward
Private Home on Upper Twin Lake, Close to Trails
₹8,630 per night
SUPERHOST
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