Winter Vacation Packages 2026

Top Winter hotels deals

Newer Luxury Getaway in a Tranquil Setting

Winter WI

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This cabin features a garden, laundry facilities, and barbecue grills.

Kitchen

Washer

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

Winter WI

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This vacation home features a garden, laundry facilities, and barbecue grills.

Kitchen

Dryer

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

Loretta WI

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This cabin features barbecue grills.

Kitchen

Pet friendly

Holiday Inn Express & Suites Hayward by IHG

15586 County Road B Hayward WI

Free Cancellation

$127 nightly

$139 total

Feb 22 - Feb 23

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and free perks like continental breakfast and free self parking.

Pool

Hot Tub

Quality Inn

700 West 9th Street Ladysmith WI

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$103 total

Feb 15 - Feb 16

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the business center and free internet in public areas. Enjoy the indoor pool and conveniences like a 24-hour front desk and free newspapers.

Pool

Breakfast included

Charming 5-bedroom cabin just outside Hayward near OO, Tiger Cat,and Spider Lake

Hayward WI

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This cabin featured laundry facilities and barbecue grills. There's fun for all ages with a playground and an arcade/game room.

Kitchen

Washer

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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.

Perch Lake

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

Black Dan Lake

Commune with nature and explore the great outdoors at Black Dan 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 120 mi 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.