Find Family Hotels in Winter, WI from CA $178

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Our top choices for Winter family-friendly hotels

Holiday Inn Express & Suites Hayward by IHG

Holiday Inn Express & Suites Hayward by IHG
2.5 star property
Hayward
9.6 out of 10, Exceptional, (657 reviews)
"Staff was very helpful and cordial and very fast during a busy check in time. "
United States
Jessica
The price is CA $163
CA $178 total
includes taxes & fees
Mar 15 - Mar 16
Holiday Inn Express & Suites Hayward by IHG

Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.

Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.
Hawkins
9.8 out of 10, Exceptional, (20 reviews)
"Great place to stay when I’m in the area and great hosts. "
United States
Paul H.
The price is CA $171
CA $209 total
includes taxes & fees
Feb 24 - Feb 25
Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Hayward
9.0 out of 10, Wonderful, (29 reviews)
"The owner was awesome, had the cabin ready for us. Gave him my eta he had cabin warming already, beds were comfortable, near the trails. We all enjoyed our visit and planning to go back before end of the snowmobile season."
United States
Henry
The price is CA $137
CA $187 total
includes taxes & fees
Feb 24 - Feb 25
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

Lakefront Cabin on LCO - The Sunset Escape

Lakefront Cabin on LCO - The Sunset Escape
Hayward
9.6 out of 10, Exceptional, (4 reviews)
"We loved the house. It was exactly as pictured and described. The view was amazing. We sat on the dock one of the evenings we were there and watched the sunset. Beautiful! The house was very clean and well stocked with things we needed. "
United States
Kerri S.
The price is CA $254
CA $713 total
includes taxes & fees
Mar 4 - Mar 5
Lakefront Cabin on LCO - The Sunset Escape

Secluded Cabin w/Fresh Snow-Hot Tub, WIFI, King

Secluded Cabin w/Fresh Snow-Hot Tub, WIFI, King
Ojibwa
10.0 out of 10, Exceptional, (46 reviews)
"We loved how remote this cabin was, it was so quiet and beautiful. We loved the property and the cabin was very clean and comfortable. Would definitely recommend if you’re looking for a lively stay in the woods. "
United States
Laura G.
The price is CA $615
CA $738 total
includes taxes & fees
Mar 4 - Mar 5
Secluded Cabin w/Fresh Snow-Hot Tub, WIFI, King

Time to Hideout in Hayward! BIRKIE WEEKEND STILL OPEN!

Time to Hideout in Hayward! BIRKIE WEEKEND STILL OPEN!
Hayward
The price is CA $262
CA $629 total
includes taxes & fees
Mar 1 - Mar 2
Time to Hideout in Hayward! BIRKIE WEEKEND STILL OPEN!

15min to trailhead, King Bed, PacMan

15min to trailhead, King Bed, PacMan
Hayward
9.6 out of 10, Exceptional, (12 reviews)
"It was a good long weekend the stay was enjoyable with good neighbors and relaxing accommodations "
United States
Kevin K.
The price is CA $509
CA $637 total
includes taxes & fees
Mar 4 - Mar 5
15min to trailhead, King Bed, PacMan

Ask about Spring Specials!-Hot Tub, EV, 2 Kings

Ask about Spring Specials!-Hot Tub, EV, 2 Kings
Hayward
9.8 out of 10, Exceptional, (21 reviews)
"My husband and our four children had a wonderful stay at Acorn Shores! The hosts were incredibly informative and very responsive to any questions we had! We enjoyed use of the canoe, kayaks, and hot tub. The amenities were perfect and we'd highly recommend this property for your next vacation get away. Thanks again for a great stay! "
United States
Mercedes S.
The price is CA $600
CA $1,246 total
includes taxes & fees
Mar 8 - Mar 9
Ask about Spring Specials!-Hot Tub, EV, 2 Kings

Dual Cabins-Hot Tub, 3 Kings, 2 Kitchens

Dual Cabins-Hot Tub, 3 Kings, 2 Kitchens
Hayward
9.8 out of 10, Exceptional, (18 reviews)
"Great property with every amenity needed."
United States
Mitchell D.
The price is CA $1,184
CA $1,480 total
includes taxes & fees
Mar 3 - Mar 4
Dual Cabins-Hot Tub, 3 Kings, 2 Kitchens
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Top Winter Hotel Reviews

Frequently asked questions

What's Winter like for family-friendly vacations?
The destination of Winter is a great choice if you've been thinking about a vacation with your kids. There are some entertaining activities you and the family might enjoy.
When's the best time to book a family-friendly vacation in Winter?
The hottest months are usually July and August with an average temp of 64°F, while the coldest months are January and February with an average of 18°F. The snowiest months in Winter are April, March, January, and February, with each month seeing an average of 10 inches of snowfall.
What's there to see and do with your family in Winter?
While you and the family are vacationing in Winter, you might want to check out some of the attractions here such as Winter Public Library, Lake Winter, and Black Dan Lake. Make sure you have lots of time for activities like Chequamegon National Forest and Flambeau River.

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