Winter Vacations from $647

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The Latest Winter vacation packages

Price found within the past 48 hours. Click for updated prices.
Love Hotels Timberline By OYO Lake Superior

Love Hotels Timberline By OYO Lake Superior

2.5 out of 5
Price was $716, price is now $647 per person
$647
per person
Jan 4 - Jan 8
found 13 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Ironwood (IWD)
6.6/10 (342 reviews)
Room was clean. But i dont know if they were working on the upper level late into the night or if a family of elephants were up there. The "remodeling " didnt appear to have been started.

Reviewed on Nov 22, 2024

Davos Chalet

Davos Chalet

2 out of 5
Price was $926, price is now $791 per person
$791
per person
Jan 4 - Jan 8
found 13 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Ironwood (IWD)
17.6/10 Exceptional! (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

North Star Retreat-kayak I Swim I Snowmobile

North Star Retreat-kayak I Swim I Snowmobile

2 out of 5
Price was $1,434, price is now $1,281 per person
$1,281
per person
Jan 4 - Jan 8
found 13 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Ironwood (IWD)
No reviews
Lakeside Haus in Presque Isle

Lakeside Haus in Presque Isle

2 out of 5
Price was $1,374, price is now $1,234 per person
$1,234
per person
Jan 4 - Jan 8
found 13 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Ironwood (IWD)
No reviews
Magnuson Hotel Ironwood

Magnuson Hotel Ironwood

2 out of 5
Price was $738, price is now $680 per person
$680
per person
Jan 4 - Jan 8
found 13 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Ironwood (IWD)
12/10 Exceptional! (283 reviews)
I've never used a virtual check in, it went smoothly. Rooms were clean but nothing super nice; we didn't expect that though. Comfortable beds and pillows Water didn't get as hot as I would have liked. Would stay here again though

Reviewed on Nov 3, 2025

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Winter Hotel Deals

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.
Holiday Inn Express & Suites Hayward by IHG

Holiday Inn Express & Suites Hayward by IHG

2.5 out of 5
15586 County Road B, Hayward, WI
Fully refundable
$127 nightly
The price is $139 total per night from Nov 30 to Dec 1
$139 total
Nov 30 - Dec 1
Total with taxes and fees
9.4/10 Exceptional! (635 reviews)
The staff is extremely friendly and efficient. Amanda at the Front Desk and attendant at breakfast on 11/11 were great!

Reviewed on Nov 12, 2025

Holiday Inn Express & Suites Hayward by IHG
Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!

Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!

Hayward WI
9.6/10 Exceptional! (208 reviews)
Well equipped, fantastic stove, comfortable furniture, awesome view, quiet and peaceful! If I had an oil well I would twist the arm of Cassidy to sell!

Reviewed on Oct 24, 2025

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Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!
See all 665 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 $647 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.