Winter Vacations from $623

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The Latest Winter vacation packages

Price found within the past 48 hours. Click for updated prices.
Quality Inn

Quality Inn

2.5 out of 5
per person
Sep 19 - Sep 21
found 20 hours ago
Roundtrip non-stop flight included
Grand Rapids (GRR) to Ironwood (IWD)
8.6/10 Excellent! (483 reviews)
It was just okay….the place needs to be freshened up.

Reviewed on Jul 1, 2025

Days Inn by Wyndham Hurley

Days Inn by Wyndham Hurley

2 out of 5
per person
Sep 19 - Sep 21
found 20 hours ago
Roundtrip non-stop flight included
Grand Rapids (GRR) to Ironwood (IWD)
8.4/10 Very Good! (825 reviews)
Very clean room with a super comfortable bed!

Reviewed on Jun 30, 2025

Snowriver Mountain Resort

Snowriver Mountain Resort

2.5 out of 5
per person
Sep 19 - Sep 21
found 20 hours ago
Roundtrip non-stop flight included
Grand Rapids (GRR) to Ironwood (IWD)
7.8/10 Good! (149 reviews)
We had a free ski lift ride which was pretty awesome.

Reviewed on Jul 5, 2025

AmericInn by Wyndham Silver City

AmericInn by Wyndham Silver City

2.5 out of 5
per person
Sep 19 - Sep 21
found 20 hours ago
Roundtrip non-stop flight included
Grand Rapids (GRR) to Ironwood (IWD)
9/10 Wonderful! (889 reviews)
The front office staff was not hospitable. The cleaning service was mediocre.

Reviewed on Jul 5, 2025

AmericInn by Wyndham Ironwood

AmericInn by Wyndham Ironwood

2.5 out of 5
per person
Sep 19 - Sep 21
found 20 hours ago
Roundtrip non-stop flight included
Grand Rapids (GRR) to Ironwood (IWD)
9/10 Wonderful! (678 reviews)
Nice location for where we were traveling to. Service was good and the breakfast was also good.

Reviewed on Jun 30, 2025

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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
8.8/10 Excellent! (17 reviews)
"Everyone was polite and very according definitely going again this summer"

Reviewed on Jun 18, 2025

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Bucktail Lodge Riverview 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
9.8/10 Exceptional! (12 reviews)
Vacation at Heaven on the Chippewa River
"Beautiful views, beautiful cabins. Great resort bar that is always full of fun people."

Reviewed on May 10, 2025

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EAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River
Rustic Cabin on Private Lake
Rustic Cabin on Private Lake
Winter
RZR trip
"Cute cabin, quiet area and beautiful lake."

Reviewed on Sep 15, 2024

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Rustic Cabin on Private Lake
See all 654 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 $623 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.