Winter Vacations from $1,058

Book a Hotel + Flight or Car together to unlock savings

The Latest Winter vacation packages

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

Magnuson Hotel Ironwood

2 out of 5
Price was $1,145, price is now $1,058 per person
$1,058
per person
Dec 24 - Dec 31
found 4 hours ago
Roundtrip non-stop flight included
Orlando (ORL) to Ironwood (IWD)
6.2/10 (339 reviews)
It smelt seemed a little suspicious wouldn’t go there again

Reviewed on Nov 4, 2026

Davos Chalet

Davos Chalet

2 out of 5
Price was $1,542, price is now $1,344 per person
$1,344
per person
Dec 24 - Dec 31
found 4 hours ago
Roundtrip non-stop flight included
Orlando (ORL) to Ironwood (IWD)
8.6/10 Excellent! (123 reviews)

Quality Inn Ironwood

Quality Inn Ironwood

2.5 out of 5
Price was $1,453, price is now $1,343 per person
$1,343
per person
Dec 24 - Dec 31
found 4 hours ago
Roundtrip non-stop flight included
Orlando (ORL) to Ironwood (IWD)
8.4/10 Very Good! (649 reviews)

Whitecap Mountains Resort

Whitecap Mountains Resort

2 out of 5
Price was $1,344, price is now $1,251 per person
$1,251
per person
Dec 24 - Dec 31
found 4 hours ago
Roundtrip non-stop flight included
Orlando (ORL) to Ironwood (IWD)
8.4/10 Very Good! (262 reviews)

Econo Lodge Hurley - Ironwood

Econo Lodge Hurley - Ironwood

2.5 out of 5
Price was $1,120, price is now $1,083 per person
$1,083
per person
Dec 24 - Dec 31
found 4 hours ago
Roundtrip non-stop flight included
Orlando (ORL) to Ironwood (IWD)
6.8/10 (229 reviews)

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Stay near popular Winter attractions

Lake Winter

Lake Winter's pristine 733-acre waters in Wisconsin offer exceptional fishing for musky, bass, and walleye. Explore by boat from two public landings or enjoy the surrounding trails for seasonal snowmobiling adventures.
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Winter Hotel Deals

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

Winter WI
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Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
Rustic Cabin on Private Lake

Rustic Cabin on Private Lake

Winter WI
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Rustic Cabin on Private Lake
EAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River

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

Loretta WI
10/10 Exceptional! (32 reviews)
"It was a wonderful cabin right along the river. We did some fishing and caught fish. Very peaceful place and the cabin was wonderful. I would definitely stay here again."

Reviewed on Oct 28, 2026

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EAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River
See all 653 properties in Winter
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.

Find the Best Winter Vacation Packages

Winter Essential Information

Language
English
Currency
U.S dollars
Population
310

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Frequently asked questions

How much does a Winter vacation package cost?
You can pick up a vacation package to this popular destination from $1,058 on Expedia. But how much your vacation to Winter costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Winter?
February, September and November are the best times to search for cheap Winter vacation packages. Traveling in less busy months means you'll typically find reduced prices on hotels and flights.
How many days is enough for Winter?
With a well-planned itinerary, you can easily hit the main Winter sights in a few days. But if you prefer to discover lesser-known spots or take day trips, think about booking your Winter vacation for longer.
How to find the best Winter package deals?
Bagging a cheap Winter package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add a few filters and see what's available. You can personalize your search by "Amenities," "Property type," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most economical Winter package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Winter vacation as a package?
You can enjoy significant savings on your Winter escape by booking a customized vacation package. Check the "Package" heading, then enter your travel dates and destination to see the best hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Winter?
If you've got your Winter travel dates locked in, book early to score some terrific deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are great for setting off on a whim.
Does Expedia offer Book Now, Pay Later Winter vacation packages?
Jet off on your dream trip to Winter with help from our Book Now, Pay Later vacations. No need to scrimp and save or wait for your next paycheck — we've partnered with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans allow you to split the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to budget for your trip and snap up bargains before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.