Book Cheap Hotels in Winter

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Check hotel availability in Winter

Tonight
Check prices in Winter for tonight, Dec 23 - Dec 24
Dec 23 - Dec 24
Tomorrow night
Check prices in Winter for tomorrow night, Dec 24 - Dec 25
Dec 24 - Dec 25
This weekend
Check prices in Winter for this weekend, Dec 26 - Dec 28
Dec 26 - Dec 28
Next weekend
Check prices in Winter for next weekend, Jan 2 - Jan 4
Jan 2 - Jan 4

Most frequently booked Winter hotels

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
6.79 km from city centre
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Book a stay at this family-friendly vacation home in Winter. Enjoy free WiFi, laundry facilities, and a pool table. Popular attractions South Barber Lake and Barber Lake are located nearby.
Kitchen
Washer
Great 4 Season Family Getaway! Quiet, yet full of Fun!

Great 4 Season Family Getaway! Quiet, yet full of Fun!

Winter WI
10.4 km from city centre
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Book a stay at this family-friendly cabin in Winter. Enjoy a pool table, patios, and cable/satellite TV service. Popular attractions Black Dan Lake and Perch Lake are located nearby.
Kitchen
Air conditioning
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
Free cancellation
41.2 km from city centre
The price is CA $154 per night
CA $154
CA $169 total
Jan 4 - Jan 5, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in Hayward. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Hayward Lake and Lumberjack Bowl are located nearby.
Pool
Hot tub
Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!

Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!

Hayward WI
34.68 km from city centre
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Stay at this cabin in Hayward. Enjoy a garden, a picnic area, and patios. Popular attractions Tiger Cat Flowage and Lake Placid are located nearby.
Kitchen
Pet-friendly
Hayward, Round Lake Retreat! Private dock, 3 kayaks, beautifully maintained!

Hayward, Round Lake Retreat! Private dock, 3 kayaks, beautifully maintained!

Hayward WI
32.85 km from city centre
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Book a stay at this beach cabin in Hayward. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Round Lake and Lovejoy Lake are located nearby.
Kitchen
Free WiFi
Modern Cabin located between Grindstone and Lac Courte Oreilles

Modern Cabin located between Grindstone and Lac Courte Oreilles

Hayward WI
32.72 km from city centre
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Stay at this cabin in Hayward. Enjoy free WiFi, an in-room coffeemaker, and in-room fireplaces. Popular attractions Grindstone Lake and Lac Courte Oreilles are located nearby.
Kitchen
Free WiFi
Big Chip Lodge. Awesome view. Dock 50' away. Authentic Historical Wisconsin.

Big Chip Lodge. Awesome view. Dock 50' away. Authentic Historical Wisconsin.

Hayward WI
17.1 km from city centre
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Book a stay at this beach lodge in Hayward. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Sister Island and Chipmunk Island are located nearby.
Pet-friendly
Free WiFi
AmericInn by Wyndham Ladysmith

AmericInn by Wyndham Ladysmith

2.5 out of 5
800 College Ave W Ladysmith WI
Free cancellation
Reserve now, pay when you stay
41.18 km from city centre
The price is CA $152 per night
CA $152
CA $170 total
Dec 30 - Dec 31
includes taxes & fees
Book a 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.
Pool
Breakfast included
Hayward Lakefront - Gorgeous Cabin, Four Seasons of Fun for up to 21 guests

Hayward Lakefront - Gorgeous Cabin, Four Seasons of Fun for up to 21 guests

Hayward WI
40.8 km from city centre
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Stay at this cabin in Hayward. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Hayward Lake and Lumberjack Bowl are located nearby.
Kitchen
Washer
Don't see what you're looking for?
See all available properties in Winter
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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.

Winter hotels essential information

Accommodation
667 hotels
Lowest Price
CA $169
Highest Price
CA $170
Popular hotels
5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis., Great 4 Season Family Getaway! Quiet, yet full of Fun!, Holiday Inn Express & Suites Hayward by IHG, Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!, Hayward, Round Lake Retreat! Private dock, 3 kayaks, beautifully maintained! , Modern Cabin located between Grindstone and Lac Courte Oreilles, Big Chip Lodge. Awesome view. Dock 50' away. Authentic Historical Wisconsin., AmericInn by Wyndham Ladysmith, Hayward Lakefront - Gorgeous Cabin, Four Seasons of Fun for up to 21 guests

Frequently asked questions

What are the top kid-friendly hotels in Winter?
Family vacations are where wonderful memories are made, but traveling with young ones can be difficult. These kid-friendly Winter hotels offer perks that aim to keep guests of all ages comfortable and happy: Bungalow Trail will help make your getaway the best one yet. It offers plenty of nice little touches, such as a playground and a firepit. Exclusive PRIVATE ISLAND for your group on Lake Winter is another top pick. After an exciting day of exploring Winter, come home to your cozy room and amenities like a playground and animal viewing activities.
Where can I find cheap hotels in Winter?
At Travelocity you'll find really nice hotels in Winter at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Winter rather than in Winter. We may find you even better rates, too.
How do I find the best Winter hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Winter then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Winter?
The cheapest hotel in Winter is CA $169 This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Winter?
There are 667 hotels in Winter on Travelocity.
What are the best hotels in Winter?
Winter has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Winter for you!
When is the best time to visit Winter?
If you want the joy of a fun-filled trip in peak season, visit Winter during March, May and July. If you'd prefer the peace of off-season, book a stay during quieter months, such as February, September and November.
When is the cheapest time to stay in Winter?
Based on historic data is usually the cheapest month to visit Winter. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Winter?
There are multiple hotels in Winter that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Winter. We have plenty of kid-friendly hotels in Winter to choose from on Travelocity!
Why book a hotel in Winter through Travelocity?
Because we have the top hotels in Winter! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Winter on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Winter hotel reviews by fellow wanderers

Cozy Cabin on Secluded Peninsula

Cozy Cabin on Secluded Peninsula

5 out of 5
Posted 9 days ago
Travelocity Verified Review
"Took a 2 day trip to celebrate an anniversary. Could have picked a better weekend as far as being able to enjoy outdoor activities. Temps never reached positive numbers during our stay. Even with that the cabin was very comfortable and cozy. "
A verified traveller stayed at Cozy Cabin on Secluded Peninsula
Cozy Cabin on Secluded Peninsula

Types of hotels

Areas of Winter