Winter Vacations from $578

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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 $609, price is now $578 per person
$578
per person
Oct 27 - Oct 29
found 4 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Ironwood (IWD)
5.2/10 (171 reviews)
Was clean, quiet, and fine for nights stay.

Reviewed on Aug 3, 2026

AmericInn by Wyndham Ironwood

AmericInn by Wyndham Ironwood

3 out of 5
Price was $708, price is now $661 per person
$661
per person
Oct 27 - Oct 29
found 4 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Ironwood (IWD)
9/10 Wonderful! (809 reviews)

Davos Chalet

Davos Chalet

2 out of 5
Price was $653, price is now $610 per person
$610
per person
Oct 27 - Oct 29
found 4 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Ironwood (IWD)
8.6/10 Excellent! (106 reviews)
The best part about this place is the sharing nature of it. There is a kitchen with plates and utensils and everything you could need to cook. There is a game room with an air hockey table and ping pong. There are TVs on each floor in the common area with couches for movie night. There are bicycles you can take out for a ride on any of the awesome trails in the area or even just the local dirt roads. There is a fire pit to drink beers around at night and a barbeque grill for summer cookouts. There is a public lake close by to go boating. This place is set up for community. We had a great time.

Reviewed on Aug 3, 2026

Days Inn by Wyndham Hurley

Days Inn by Wyndham Hurley

2 out of 5
Price was $696, price is now $652 per person
$652
per person
Oct 27 - Oct 29
found 4 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Ironwood (IWD)
8.4/10 Very Good! (944 reviews)
Good breakfast, clean and quiet

Reviewed on Aug 4, 2026

Magnuson Hotel Ironwood

Magnuson Hotel Ironwood

2 out of 5
Price was $613, price is now $599 per person
$599
per person
Oct 27 - Oct 29
found 4 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Ironwood (IWD)
6.2/10 (318 reviews)
no staff on site and shower had mold around the faucet and handle.

Reviewed on Jul 30, 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! (34 reviews)
"Perfect little cabin with a river view for our relaxing getaway! Had everything we needed."

Reviewed on Jul 20, 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 662 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 $578 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.