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Top Winter hotels deals

5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.

5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.

Winter WI
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Book a stay at this family-friendly vacation home in Winter. Enjoy free WiFi, laundry facilities, and a pool table. Popular attractions South Barber Lake and Barber Lake are located nearby.
Kitchen
Washer
Holiday Inn Express & Suites Hayward by IHG

Holiday Inn Express & Suites Hayward by IHG

2.5 out of 5
15586 County Road B Hayward WI
The price is CA $154 per night
CA $154
CA $169 total
Jan 4 - Jan 5, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in Hayward. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Hayward Lake and Lumberjack Bowl are located nearby.
Pool
Hot tub
Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!

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

Hayward WI
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Stay at this cabin in Hayward. Enjoy a garden, a picnic area, and patios. Popular attractions Tiger Cat Flowage and Lake Placid are located nearby.
Kitchen
Pet-friendly
Hayward, Round Lake Retreat! Private dock, 3 kayaks, beautifully maintained!

Hayward, Round Lake Retreat! Private dock, 3 kayaks, beautifully maintained!

Hayward WI
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Book a stay at this beach cabin in Hayward. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Round Lake and Lovejoy Lake are located nearby.
Kitchen
Free WiFi
Modern Cabin located between Grindstone and Lac Courte Oreilles

Modern Cabin located between Grindstone and Lac Courte Oreilles

Hayward WI
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Stay at this cabin in Hayward. Enjoy free WiFi, an in-room coffeemaker, and in-room fireplaces. Popular attractions Grindstone Lake and Lac Courte Oreilles are located nearby.
Kitchen
Free WiFi
Big Chip Lodge. Awesome view. Dock 50' away. Authentic Historical Wisconsin.

Big Chip Lodge. Awesome view. Dock 50' away. Authentic Historical Wisconsin.

Hayward WI
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Book a stay at this beach lodge in Hayward. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Sister Island and Chipmunk Island are located nearby.
Pet-friendly
Free WiFi
Don't see what you're looking for?
See all available properties in Winter
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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.

Popular places to visit

Lake Winter

Commune with nature and explore the great outdoors at Lake Winter during your travels in Winter.

Lake Winter

Fishtrap Lake

Commune with nature and explore the great outdoors at Fishtrap Lake during your travels in Winter.

Fishtrap Lake

Perch Lake

Commune with nature and explore the great outdoors at Perch Lake during your travels in Winter.

Perch Lake

Frequently asked questions

How much are vacation packages to Winter?
Treat yourself to a one-of-a-kind experience in Winter with a vacation package starting from just . Booking flights and hotels with Travelocity is a piece of cake. And even better, our package deals will leave you with more savings in your pocket for fun.
How long should my Winter vacation be?
Generally, 4 nights is how long the majority of people spend familiarizing themselves with Winter. Not sure if that'll be sufficient time to do everything on your must-do list? Stay another night or two and experience everything this place has to offer.
Where can I get the best vacation package deals for Winter?
With as many as 400 airlines and 1,000,000 hotels around the world, it's hard to top Travelocity. Scroll through our impressive range and create the perfect Winter vacation package. Don't you love it when vacation planning is that easy?
Why should I purchase my Winter vacation bundle via Travelocity?
From our 24/7 customer care to our range of terrific destinations, we're dedicated to giving you the vacation of a lifetime. All you have to do is to click and book — our Price Match Guarantee will ensure you score the best price.
Will I save money on my Winter car rental if I combine it with a hotel or flight?
Bundling your hotel, car and flight into a Winter vacation package is a surefire way to score an incredible deal. Plus, having your own rental car gives you freedom to find your way to all the landmarks you're itching to check out. Sitting 193 kilometers away from Winter, Xcel Energy Center is one attraction that should be on your agenda. Load up the car and make a day trip of it.
Where should I stay when visiting Winter?
If you're after somewhere to spend your nights, have a look at the Private, Pet Friendly Lakefront Cabin. It's the top choice for many travelers.

Photos of local treasures

Browse Winter vacation photos for more inspiration