Winter Vacations

Book a Hotel + Flight or Car together to unlock savings

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 Dec 14 to Dec 15
$139 total
Dec 14 - Dec 15
Total with taxes and fees
9.4/10 Exceptional! (640 reviews)
Amazing stay with pretty lake views, and wonderful with two young kids. Big, open common spaces with activities/games for adults and kids. Pool was great, hot tub jets were not working but it was hot and circulating, sauna was hot and spacious but the benches could use fixing. Room was recently renovated, ...

Reviewed on Nov 30, 2025

Holiday Inn Express & Suites Hayward by IHG
Northern Lights Inn

Northern Lights Inn

2.5 out of 5
1113 S 4th Ave Park Falls WI
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $111 total per night from Dec 18 to Dec 19
$111 total
Dec 18 - Dec 19
Total with taxes and fees
7.8/10 Good! (188 reviews)
Everything was great

Reviewed on Nov 29, 2025

Northern Lights Inn
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 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.