Winter Vacations from $481

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The Latest Winter vacation packages

Price found within the past 48 hours. Click for updated prices.
Silver Street Motel by OYO

Silver Street Motel by OYO

2.5 out of 5
Price was $575, price is now $481 per person
$481
per person
Aug 23 - Aug 28
found 15 hours ago
Roundtrip flight included
Chicago (ORD) to Ironwood (IWD)
5/10 (167 reviews)
The location was great. The room had a musty smell.

Reviewed on Jul 20, 2026

Days Inn by Wyndham Hurley

Days Inn by Wyndham Hurley

2 out of 5
Price was $842, price is now $742 per person
$742
per person
Aug 23 - Aug 28
found 15 hours ago
Roundtrip flight included
Chicago (ORD) to Ironwood (IWD)
8.4/10 Very Good! (940 reviews)
.

Reviewed on Jul 21, 2026

Indianhead Ironwood Motel

Indianhead Ironwood Motel

2.5 out of 5
Price was $639, price is now $578 per person
$578
per person
Aug 23 - Aug 28
found 15 hours ago
Roundtrip flight included
Chicago (ORD) to Ironwood (IWD)
8/10 Very Good! (325 reviews)
The room was clean and the bed was comfortable. Some issues with the t.v. would shut off and could not get it to go to channels. Lights would blink low to low light; seemed to be a power draw issue maybe. Easy check in. Very helpful in helping me do that.

Reviewed on Jul 22, 2026

Magnuson Hotel Ironwood

Magnuson Hotel Ironwood

2 out of 5
Price was $613, price is now $562 per person
$562
per person
Aug 23 - Aug 28
found 15 hours ago
Roundtrip flight included
Chicago (ORD) to Ironwood (IWD)
6.2/10 (318 reviews)
Room was paid for in advance. Upon arriving, my son paid an extra $20 for early check on, and they ended up charging him a second time for the entire room. The keyosk was down and would no issue keys, so we ended up leaving. When contacting the hotel about it the next day, they claimed that they called as soon as we left to say we could come back, which was not true. We received no call. On top of that, we now paid for the room twice me

Reviewed on Jul 12, 2026

Davos Chalet

Davos Chalet

2 out of 5
Price was $676, price is now $632 per person
$632
per person
Aug 23 - Aug 28
found 15 hours ago
Roundtrip flight included
Chicago (ORD) to Ironwood (IWD)
8.6/10 Excellent! (103 reviews)

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Stay near popular Winter attractions

Perch Lake

This pristine 129-acre lake in Wisconsin's Chequamegon National Forest boasts six fish species for anglers to pursue. Bring your own canoe to explore its clear waters surrounded by tranquil forest scenery.
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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
8.4/10 Very Good! (32 reviews)
"Great weekend get away! Everyone is so nice."

Reviewed on Jul 5, 2026

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Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
Bucktail Lodge Lakeview Cabin on Barker Lake in Winter, Wisconsin

Bucktail Lodge Lakeview Cabin on Barker Lake in Winter, Wisconsin

Winter WI
8.8/10 Excellent! (12 reviews)
"Comfortable bed"

Reviewed on Jul 2, 2026

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Bucktail Lodge Lakeview Cabin on Barker Lake in Winter, Wisconsin
Bears Den on the private lake

Bears Den on the private lake

Winter WI
9.6/10 Exceptional! (29 reviews)
"This was a great 2 night stay. Plenty of room for our group."

Reviewed on Feb 22, 2026

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Bears Den on the private lake
See all 669 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 $481 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.