Book Exclusive Winter Vacation Packages

Choose one or more items to build your trip:

Top Winter hotels deals

Bears Den on the private lake

Bears Den on the private lake

Get rates
Stay at this family-friendly vacation home in Winter. Enjoy free WiFi, onsite parking, and a garden. Discover genuine guest reviews for Bears Den on the private lake along with the latest prices and availability – book now.
Kitchen
Barbecue grill
Spacious Winter Retreat w/ River Access + Kayaks!

Spacious Winter Retreat w/ River Access + Kayaks!

Get rates
Stay at this family-friendly vacation home in Winter. Enjoy onsite parking, an arcade/game room, and an in-room DVD player. Popular attractions Ojibwa State Park and Lake Chippewa are located nearby. Discover genuine guest reviews for Spacious Winter Retreat w/ River Access + Kayaks! along with the latest prices and availability – book now.
Outdoor space
Water view
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

Get rates
Stay at this cabin in Winter. Enjoy WiFi, barbecue grills, and a TV. Popular attraction Lake Chippewa is located nearby. Discover genuine guest reviews for Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin along with the latest prices and availability – book now.
Pet-friendly
Kitchen
GREAT PLACE OPENS JULY 7

GREAT PLACE OPENS JULY 7

Get rates
Stay at this family-friendly cabin in Winter. Enjoy free WiFi, onsite parking, and a garden. Discover genuine guest reviews for GREAT PLACE OPENS JULY 7 along with the latest prices and availability – book now.
Holiday Inn Express & Suites Hayward, an IHG Hotel

Holiday Inn Express & Suites Hayward, an IHG Hotel

2.5 out of 5
15586 County Road B, Hayward, WI
Free cancellation
The price is CA $192 per night
CA $192
per night
May 12 - May 13
Stay at this business-friendly hotel in Hayward. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Hayward Lake and Lumberjack Bowl are located nearby. Discover genuine guest reviews for Holiday Inn Express & Suites Hayward, an IHG Hotel along with the latest prices and availability – book now.
Cobblestone Hotels & Suites – Ladysmith

Cobblestone Hotels & Suites – Ladysmith

2.5 out of 5
700 West 9th Street, Ladysmith, WI
Free cancellation
Reserve now, pay when you stay
The price is CA $176 per night
CA $176
per night
May 5 - May 6
Stay at this business-friendly hotel in Ladysmith. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Memorial Park and The Tee-Away Golf Course and Supper Club are located nearby. Discover genuine guest reviews for Cobblestone Hotels & Suites – Ladysmith along with the latest prices and availability – book now.
Pool
Breakfast included
Don't see what you're looking for?
See all available properties in Winter
View all properties
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.

Frequently asked questions

How much are vacation packages to Winter?
Travelocity offers flight and hotel packages from just . With such great bargains, you’ll be exploring all of Winter in no time.
Where can I get the best vacation package deals for Winter?
For a fun and affordable package deal to Winter, book with Travelocity. Take your pick of 400 partner airlines and 665,000 properties worldwide to create the ultimate trip — it’s really that easy.
Why should I book my Winter vacation bundle with Travelocity?
From enchanting destinations to memorable experiences, we have everything you need to satisfy your travel desires. Our 24/7 support will also make sure you’re being well taken care of while you’re on your trip. And don’t worry if you find a lower price on your reservation, we’ll match it. That’s our Price Match Guarantee.
Can I save money on my Winter car rental if I book it with my hotel or flight?
Certainly — bundle your car, hotel and flight into a Winter vacation package and you’ll save plenty. With so much to see in the Winter area, having your own wheels will make it easy to explore. Once you’ve slid into the driver’s seat, crank up the tunes and head to Xcel Energy Center, an unmissable attraction around 190 kilometersfrom Winter.
What is the best time of year to go to Winter?
If you need to watch your pennies, is a terrific month to visit Winter, while is the priciest time of year. is regarded as the peak season. If you’d prefer to dodge the crowds, are usually quieter.
What is there to do in Winter?
Lake Chippewa is just one of the superb sights that make Winter such a great place to visit. But give yourself enough time to experience its lesser-known attractions too. This is often where the best vacation memories are created.
Where should I stay when visiting Winter?
If you’re searching for somewhere to spend your nights, consider the Bring the Family to This Wonderful Log Cabin on Connors Lake!. It’s the top choice for many travelers.
Can I go on vacation to Winter at this time?
Don’t plan your trip to Winter without up-to-date facts about quarantine policies and travel restrictions. Travelocity’s Covid-19 Travel Advisor can fill in the blanks. It has all the info you need to make your vacation and flight as relaxed as possible.