Winter Vacations from $989
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The Latest Winter vacation packages
Price found within the past 48 hours. Click for updated prices.
Cedars Motel
$989
per person
Dec 10 - Dec 13
found 17 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Ironwood (IWD)
9.4/10 Exceptional! (414 reviews)
The room was exceptionally clean. The bed was absolutely awful, it was like sleeping on a concrete floor. The bath towels were short almost the same size as the hand towels. I was grateful to have a conversation with the owner upon checkout and she was very kind in her explanation about the bed situation although I wish she would have given us a partial credit back for the inconvenience, but unfortunately that didn't happen. We also discussed the size of the bath towels; we did receive longer ones upon request the day before checkout and it was explained to us that apparently they just received them.
Reviewed on Oct 15, 2026
Davos Chalet
$1,059
per person
Dec 10 - Dec 13
found 17 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Ironwood (IWD)
8.6/10 Excellent! (118 reviews)
Expedia did a poor job of letting us know it was self check in. Instructions were terrible.
We came in at night and there was no outside lights and poor signage to find the chalet. Had to get help from another resort to locate.
Reviewed on Oct 15, 2026
Stay near popular Winter attractions
Lake Winter
Lake Winter's pristine 733-acre waters in Wisconsin offer exceptional fishing for musky, bass, and walleye. Explore by boat from two public landings or enjoy the surrounding trails for seasonal snowmobiling adventures.
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.
Barker Lake
This 213-acre Wisconsin lake offers pristine waters teeming with musky, bass, and walleye for fishing enthusiasts. Explore by kayak in summer or try ice fishing during winter months when the landscape transforms.
Fishtrap Lake
Fishtrap Lake's 263 acres teem with musky, bass, and walleye in the serene Wisconsin wilderness. Anglers appreciate the public boat landing and the lake's shallow 11-foot depth that creates ideal fishing conditions.
Little Cranberry Lake
This secluded 9-acre Wisconsin lake offers pristine waters reflecting dense spruce forests. Anglers appreciate its peaceful atmosphere and healthy panfish population, best enjoyed at dawn or dusk.
Connors Lake
Commune with nature and explore the great outdoors at Connors Lake during your travels in Winter.
Bluegill Lake
Bluegill Lake offers pristine waters teeming with panfish and largemouth bass in Wisconsin's serene Oneida County. Anglers can enjoy peaceful fishing experiences during early mornings when fish are most active.
Black Dan Lake
Black Dan Lake's crystal-clear waters attract anglers seeking musky, bass, and walleye in tranquil Wisconsin. Paddle through calm waters surrounded by pine forests where wildlife enhances the serene experience.
Winter Hotel Deals
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
Winter WI
8.6/10 Excellent! (37 reviews)
"Friendly host, simple cabins right on the water as described"
Reviewed on Oct 4, 2026
EAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River
Loretta WI
10/10 Exceptional! (31 reviews)
"Very nice place , would have been nice for the bar area to be open earlier."
Reviewed on Sep 20, 2026
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 |
More vacations you might like
Frequently asked questions
How much does a Winter vacation package cost?
You can pick up a vacation package to this popular destination from $989 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.
