Winter Vacations 2026

Top Winter hotels deals

Amazing Sunsets, Peaceful, Well Maintained Lake home on Beautiful, Barker lake

Winter WI

Stay at this vacation home in Winter. Enjoy a beach locale, a garden, and laundry facilities. Popular attractions Barker Lake and Barker Lake Golf Course are located nearby.

Kitchen

Dryer

EAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River

Loretta WI

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Stay at this cabin in Winter. Enjoy free WiFi, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Fishtrap Lake and Bluegill Lake are located nearby.

Kitchen

Pet-friendly

The Lodge on Lake of the Pines - enjoy the Northwoods in comfort!

Loretta WI

CA $431

CA $809 total

May 20 - May 21

includes taxes & fees

Stay at this lodge in Winter. Enjoy free WiFi, a garden, and laundry facilities.

Free WiFi

Air conditioning

GREAT PLACE OPENS JULY 7

Park Falls WI

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Book a stay at this family-friendly cabin in Winter. Enjoy free WiFi, a garden, and laundry facilities.

Kitchen

Washer

Luxury Cabin, 800+ feet frontage, 733 acre Lake, Hot tub, Pontoon, Fireplace .

Winter, Wisconsin WI

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Stay at this cabin in Winter. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Lake Winter and Winter Public Library are located nearby.

Holiday Inn Express & Suites Hayward by IHG

15586 County Road B Hayward WI

Free cancellation

CA $208

CA $228 total

May 21 - May 22

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

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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.

Fishtrap Lake

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

Perch Lake

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

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.