Winter Vacation Packages 2026 from $752

Winter flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Silver Street Motel by OYO

$752

per person

Oct 5 - Oct 9

found 1 day ago

Roundtrip non-stop flight included

Houston (IAH) to Ironwood (IWD)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.

Days Inn by Wyndham Hurley

$923

per person

Sep 14 - Sep 18

found 1 day ago

Roundtrip non-stop flight included

Houston (IAH) to Ironwood (IWD)

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

Davos Chalet

$818

per person

Oct 5 - Oct 9

found 1 day ago

Roundtrip non-stop flight included

Houston (IAH) to Ironwood (IWD)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Enjoy ski-in/ski-out access and onsite ski storage. Enjoy the sauna and conveniences like a communal living room and barbecue grills.

Whitecap Mountains Resort

$897

per person

Oct 5 - Oct 9

found 1 day ago

Roundtrip non-stop flight included

Houston (IAH) to Ironwood (IWD)

Ski-in/ski-out access and a restaurant are featured at this smoke-free hotel. There's a free ski shuttle, and ski lessons, ski rentals and ski passes are available on site. Enjoy the indoor pool and perks like free self parking and free WiFi.

Indianhead Ironwood Motel

$792

per person

Oct 5 - Oct 9

found 1 day ago

Roundtrip non-stop flight included

Houston (IAH) to Ironwood (IWD)

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A virtual front desk are provided for your convenience.

Top Winter hotels deals

Bucktail Lodge Lakeview Cabin on Barker Lake in Winter, Wisconsin

Winter WI

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This cabin features barbecue grills.

Kitchen

Pet friendly

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

Winter WI

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This cabin includes a garden and barbecue grills.

Kitchen

Pet friendly

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

Rustic Cabin on Private Lake

Winter WI

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This cabin features barbecue grills.

Kitchen

Pet friendly

Bears Den on the private lake

Winter WI

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

Kitchen

Washer

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

Winter, Wisconsin WI

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A hot tub is featured at this cabin, along with laundry facilities and barbecue grills.

Hot Tub

Kitchen

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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.

Stay near popular Winter attractions

Perch Lake

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

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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 $752. 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.