Winter Vacations from $546

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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 $589, price is now $546 per person
$546
per person
Mar 19 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Ironwood (IWD)
6/10 (283 reviews)
The staff was amazing would definitely recommend them

Reviewed on Jan 19, 2026

Davos Chalet

Davos Chalet

2 out of 5
Price was $715, price is now $597 per person
$597
per person
Mar 19 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Ironwood (IWD)
8.8/10 Excellent! (94 reviews)
It was such a beauitful place to stay especially with the fall colors. There were community snacks including s’mores which was such a great surprise!

Reviewed on Oct 22, 2025

Quality Inn Ironwood

Quality Inn Ironwood

2.5 out of 5
Price was $692, price is now $629 per person
$629
per person
Mar 19 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Ironwood (IWD)
8.6/10 Excellent! (535 reviews)
Clean rooms,staff was great

Reviewed on Jan 5, 2026

Indianhead Ironwood Motel

Indianhead Ironwood Motel

2.5 out of 5
Price was $599, price is now $552 per person
$552
per person
Mar 19 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Ironwood (IWD)
7.8/10 Good! (275 reviews)
Trailer parking a bit tight, over all good stay and would do it again

Reviewed on Jan 28, 2026

AmericInn by Wyndham Ironwood

AmericInn by Wyndham Ironwood

2.5 out of 5
Price was $717, price is now $665 per person
$665
per person
Mar 19 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Ironwood (IWD)
8.8/10 Excellent! (759 reviews)
Clean room, Great access to snomobile trail. Would stay again.

Reviewed on Jan 29, 2026

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Winter Hotel Deals

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
9.8/10 Exceptional! (20 reviews)
Everything was exceptional!

Reviewed on Oct 18, 2025

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EAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River
Newer Luxury Getaway in a Tranquil Setting

Newer Luxury Getaway in a Tranquil Setting

Winter WI
10/10 Exceptional! (89 reviews)
This is our second stay. We love the area and the cabin. Brings back memories of staying at my grandparents home when I was little.

Reviewed on Oct 21, 2025

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Newer Luxury Getaway in a Tranquil Setting
5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.

5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.

Winter WI
9.8/10 Exceptional! (68 reviews)
We rent someplace in the Winter area every year in October for a weeklong grouse hunt. This cabin was by far our favorite. It was exceptionally cleaned, well kept, well stocked, and well laid out. Chris was a fantastic and accommodating host and made sure everything was set for our arrival. I would ...

Reviewed on Oct 29, 2025

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5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.
See all 690 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 $546 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.