Search vacation rentals in Winter from 100+ sites!

Find the best offers in Winter

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Winter vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Winter Vacation rentals: no available offers. Here are other great options for your stay!

Spacious Cabin On The Chippewa River - Winter
8.7 6 reviews
Winter
08/25 – 09/03
$400/nighttotal: $3600 (9 )

Spacious Cabin On The Chippewa River

3 4
apartment , Winter
Three Little Birds Cabin is located near Winter, Wisconsin, six miles from downtown Winter and six miles from the Tuscobia State Trail, offering easy access to the Chippewa River and Flowage.
This three-bedroom, three-bathroom lodge sleeps up to twelve guests and features a modern-rustic interior, a full kitchen with dishwasher, air conditioning, a fireplace, a deck overlooking the river, and ample parking for trailers, perfect for kayaking, fishing, snowmobiling, and ATV riding.
The Lakeside: Hot Tub Ice Fishing Snowmobile Trail - Winter
9.8 32 reviews
Winter
10/18 – 10/22
$382/nighttotal: $1528 (4 )

The Lakeside: Hot Tub Ice Fishing Snowmobile Trail

1 2
apartment , Winter
The Lakeside, a four-bedroom vacation home on Lake Winter in Sawyer County, Wisconsin, offers direct access to the Tuscobia State Trail.
This eight-guest rental boasts a fully equipped kitchen, a hot tub, a wrap-around deck with a firepit, and complimentary kayak and stand-up paddleboard use (seasonal); a pontoon boat rental is also available for exploring the lake.
Gateway To The Great North Woods By Donbar - Winter
9.9 128 reviews
Winter
10/18 – 10/22
$175/nighttotal: $700 (4 )

Gateway To The Great North Woods By Donbar

3 2
apartment , Winter
This 3-bedroom apartment is located on the Tuscobia State Trail in Winter, Wisconsin, just a short drive from lakes, Hayward, and Ladysmith. The apartment has received excellent ratings for location, cleanliness, and user experience.
The apartment can comfortably accommodate up to 10 guests and features a fully equipped kitchen, two TVs with streaming services, a fireplace, and a private entrance. Enjoy the Northwoods beauty year-round with access to the Tuscobia State Trail, lakes for fishing and boating, and family-friendly amenities like a pack and play, highchair, and booster seats.
Big Chip Outdoors - 4 Bedroom House With Wifi & Ac In Heart Of Chippewa Flowage - Winter
10 6 reviews
Winter
08/12 – 08/15
$716/nighttotal: $2148 (3 )

Big Chip Outdoors - 4 Bedroom House With Wifi & Ac In Heart Of Chippewa Flowage

4 2
apartment , New Post
This Hayward vacation home sits on 11 private acres, a short 1/8 mile from the Chippewa Flowage South boat landing and directly on ATV/UTV/snowmobile trails, offering easy access to public hiking and snowshoeing trails.
This four-bedroom, two-bathroom house comfortably sleeps ten guests with four queen beds and two twin cots, boasting modern amenities including two Blackstone griddles, a heated garage with a bar, and a washer/dryer on both levels; enjoy outdoor cooking, nearby boating on the Chippewa Flowage, and miles of trails.

Frequently Asked Questions about vacation rentals in Winter

Destinations nearby

©2026 cozycozy.com