Find Family Hotels in Winter, WI from CA $105

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Check availability on Winter Family Hotels

Top Winter Family Hotels

Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!
Interior

Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!

9.6 out of 10, Exceptional, (198)
"It would be difficult to find a cottage with a better lake view than this one. It's our second time here and we love it. Very comfortable in every respect."
The price is CA $135
CA $410 total
includes taxes & fees
Aug 20 - Aug 21
Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Property grounds

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

9.6 out of 10, Exceptional, (7)
"Quiet resort. I really enjoyed spending time with my family and just getting away for a week."
The price is CA $241
CA $318 total
includes taxes & fees
Sep 1 - Sep 2
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Your Ideal Up-North Family Retreat Home on Lac Courte Oreilles
Interior

Your Ideal Up-North Family Retreat Home on Lac Courte Oreilles

10.0 out of 10, Exceptional, (100)
"House is perfect size for a large family and lake is beautiful."
The price is CA $688
CA $1,435 total
includes taxes & fees
Aug 26 - Aug 27
Your Ideal Up-North Family Retreat Home on Lac Courte Oreilles
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Fridge, microwave, oven, stovetop

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

9.2 out of 10, Wonderful, (24)
"Absolutely wonderful stay, very cabin like and rustic. Wished the TV worked for the kids at night, other than that, it was a great stay. "
The price is CA $241
CA $318 total
includes taxes & fees
Sep 1 - Sep 2
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Property grounds

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

9.6 out of 10, Exceptional, (20)
"My stay in cabin 2 was great. Spent our time fishing and exploring the area. Be aware the water level is low this time of year. I would recommend this resort to a friend. "
The price is CA $207
CA $272 total
includes taxes & fees
Sep 1 - Sep 2
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
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.

Top Winter Hotel Reviews

Holiday Inn Express & Suites Hayward by IHG

Holiday Inn Express & Suites Hayward by IHG

10/10 Excellent
"✌"
John 1-night trip
Posted 4 days ago
Holiday Inn Express & Suites Hayward by IHG

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.
What's the best place to stay for families in Winter?
"Upscale Accommodations" with an "Up North" location! is a resort with in-room kitchens and free WiFi, and it's a top choice on Expedia for families. Other good options to stay with the kids include Historic prohibition Lodge next to golf course with private beach and "Upscale Accommodations" with an "Up North" location!.
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 are visiting Winter, you might want to round up the kiddos and make time to see interesting attractions such as Chequamegon National Forest and Winter Public Library. Make sure you have lots of time for activities like Lake Winter and Bluegill Lake.