Winter Vacations from $864

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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 $957, price is now $864 per person
$864
per person
Sep 25 - Sep 30
found 3 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Ironwood (IWD)
5.2/10 (171 reviews)

Lakeside Haus in Presque Isle

Lakeside Haus in Presque Isle

2 out of 5
Price was $2,294, price is now $2,024 per person
$2,024
per person
Sep 25 - Sep 30
found 3 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Ironwood (IWD)
No reviews

Days Inn by Wyndham Hurley

Days Inn by Wyndham Hurley

2 out of 5
Price was $1,261, price is now $1,134 per person
$1,134
per person
Sep 25 - Sep 30
found 3 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Ironwood (IWD)
8.4/10 Very Good! (944 reviews)
Very clean rooms, breakfast was good, pool felt good to soak in, whirlpool actually worked good and staff was friendly.

Reviewed on Jul 31, 2026

Indianhead Ironwood Motel

Indianhead Ironwood Motel

2.5 out of 5
Price was $996, price is now $924 per person
$924
per person
Sep 25 - Sep 30
found 3 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Ironwood (IWD)
8/10 Very Good! (326 reviews)

Davos Chalet

Davos Chalet

2 out of 5
Price was $1,055, price is now $987 per person
$987
per person
Sep 25 - Sep 30
found 3 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Ironwood (IWD)
8.6/10 Excellent! (104 reviews)
Wonderful view for how cheap of a stay it is. The staff less check in process was great for introvert who would not like to deal with people. They also have some amenity rooms you can hang out with friends or other guests.

Reviewed on Jul 29, 2026

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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
8.6/10 Excellent! (33 reviews)
"We had a great 2 night stay for a guys weekend of fishing and golf. The cabin was exactly what we needed. It has everything you need and more. A/C cooled the cabin well, the beds were comfortable, and the cabin was good and clean.When you stay make sure to stop in to the bucktail bar and grill and ..."

Reviewed on Jul 12, 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
8.6/10 Excellent! (13 reviews)
"Overall the cabins were okay to stay at for a short trip, unfortunately we were not able to get our wifi working so unable to watch tv the entire time. Did have a musty smell overall but was livable. I really just wish the wifi was stronger and working better for early risers and people that like ..."

Reviewed on Jul 12, 2026

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Bucktail Lodge Lakeview Cabin on Barker Lake in Winter, Wisconsin
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
10/10 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 666 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 $864 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.