Winter Vacations from $1,141

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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 $1,310, price is now $1,141 per person
$1,141
per person
Oct 5 - Oct 9
found 3 hours ago
Roundtrip non-stop flight included
Louisville (SDF) to Ironwood (IWD)
5/10 (167 reviews)
A very poor motel. Very unclean with terrible bathroom.

Reviewed on Jul 24, 2026

Indianhead Ironwood Motel

Indianhead Ironwood Motel

2.5 out of 5
Price was $1,343, price is now $1,188 per person
$1,188
per person
Oct 5 - Oct 9
found 3 hours ago
Roundtrip non-stop flight included
Louisville (SDF) to Ironwood (IWD)
8/10 Very Good! (325 reviews)

Magnuson Hotel Ironwood

Magnuson Hotel Ironwood

2 out of 5
Price was $1,324, price is now $1,175 per person
$1,175
per person
Oct 5 - Oct 9
found 3 hours ago
Roundtrip non-stop flight included
Louisville (SDF) 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

Quality Inn Ironwood

Quality Inn Ironwood

2.5 out of 5
Price was $1,530, price is now $1,367 per person
$1,367
per person
Oct 5 - Oct 9
found 3 hours ago
Roundtrip non-stop flight included
Louisville (SDF) to Ironwood (IWD)
8.6/10 Excellent! (595 reviews)
Air conditioning unit was very noisy. Other than that the stay was great.

Reviewed on Jul 24, 2026

Snow Chasers Lodge

Snow Chasers Lodge

3.5 out of 5
Price was $1,397, price is now $1,267 per person
$1,267
per person
Oct 5 - Oct 9
found 3 hours ago
Roundtrip non-stop flight included
Louisville (SDF) to Ironwood (IWD)
8/10 Very Good! (88 reviews)
I wish there were staff on-site part of the time, just in case there is a problem or someone has questions. On the booking site, it would state that no one is on-site.

Reviewed on Jul 24, 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
8.4/10 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
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
10/10 Exceptional! (25 reviews)
"Quiet, on the river. Great place to get away. Awesome 3 day get away. We had a couple of goals for this trip: 1 On water. 2 Remote location. 3. Quiet and peaceful setting. This met everything we wanted. Thank you for a great get away."

Reviewed on Jul 8, 2026

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EAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River
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 $1,141 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.