A snowy landscape with a red barn and a red shed.

Find hotels in Winter, WI from $92

  • Upfront pricing

    Our total price for your stay includes taxes and fees
  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Filter by

Star rating

Guest rating

Selecting then applying a filter from this group will update the results on a new page

Our top choices for Winter hotels

1. AmericInn by Wyndham Ladysmith

AmericInn by Wyndham Ladysmith
3.0 star property
Ladysmith
8.2 out of 10, Very good, (133 reviews)
"Clean big room. I would definitely stay here again."
United States
Sara
August 25th, 2026
$105 nightly
The price is $117
Nov 15 - Nov 16
Total with taxes and fees
AmericInn by Wyndham Ladysmith

2. Quality Inn Ladysmith

Quality Inn Ladysmith
2.5 star property
Ladysmith
8.8 out of 10, Excellent, (299 reviews)
"I like the large pool and jacuzzi."
United States
Brenda
20 days ago
$110 nightly
The price is $122
Nov 29 - Nov 30
Total with taxes and fees
Quality Inn Ladysmith

3. Luxury 7,500‑Sq‑Ft Lakefront Lodge, Private Dock & Snowmobile Access

Luxury 7,500‑Sq‑Ft Lakefront Lodge, Private Dock & Snowmobile Access
Hayward
10.0 out of 10, Exceptional, (127 reviews)
"Amazing cabin, Great location, Very responsive Host. Will try to book this cabin again next year"
United States
Patrick M.
Luxury 7,500‑Sq‑Ft Lakefront Lodge, Private Dock & Snowmobile Access

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

Big Chip Lodge. Awesome view. Dock 50' away. Authentic Historical Wisconsin.
Hayward
9.2 out of 10, Wonderful, (141 reviews)
"We had a great time again at your cabin with multi generational friendsand family!!Thank you,Mike and Joey"
United States
RGO FAMILY O.
Big Chip Lodge. Awesome view. Dock 50' away. Authentic Historical Wisconsin.

5. Historic prohibition Lodge next to golf course with private beach

Historic prohibition Lodge next to golf course with private beach
Winter
10.0 out of 10, Exceptional, (4 reviews)
"We had a wonderful stay! The accommodations were outstanding and perfect for our family reunion. The hosts were there to greet us when we arrived and very responsive during our stay. We will definitely be back!"
United States
Kellie K.
Historic prohibition Lodge next to golf course with private beach

6. Lakewoods Resort & Lodge

Lakewoods Resort & Lodge
2.5 star property
Cable
6.8 out of 10, (6 reviews)
"Lakewoods resort was a blast. They had plenty of parking for trailer."
United States
Johnny
Lakewoods Resort & Lodge

7. Northwoods Motels

Northwoods Motels
2.5 star property
Ladysmith
6.6 out of 10, (153 reviews)
"The lady at the desk was nice."
United States
JASON
$110 nightly
The price is $116
Nov 9 - Nov 10
Total with taxes and fees
Northwoods Motels

8. The Lodge on Lake of the Pines - enjoy the Northwoods in comfort!

The Lodge on Lake of the Pines - enjoy the Northwoods in comfort!
Loretta
9.8 out of 10, Exceptional, (16 reviews)
"Place was amazing! Beautiful inside and out. The whole family loved it! Host was quick to respond. Would love to go back"
United States
Kayla E.
The Lodge on Lake of the Pines - enjoy the Northwoods in comfort!

9. Log Home in the NATIONAL FOREST. ATV/SNOWMOBILE TRAIL CROSS OUR PROPERTY

Log Home in the NATIONAL FOREST. ATV/SNOWMOBILE TRAIL CROSS OUR PROPERTY
Hayward
9.6 out of 10, Exceptional, (163 reviews)
"We had a fantastic time at this place. Very clean and so much room for everyone. Had everything we needed. Also was thankful for the use of the washer and dryer to wash swim suits and towels. Very quiet and sits back off the road which was a plus for my family."
United States
Stacey R.
Log Home in the NATIONAL FOREST. ATV/SNOWMOBILE TRAIL CROSS OUR PROPERTY

10. Northwoods Rustic Lodge steps away from Round Lake in Richardson Bay & Pontoon

Northwoods Rustic Lodge steps away from Round Lake in Richardson Bay & Pontoon
Hayward
9.6 out of 10, Exceptional, (25 reviews)
"The lodge is eclectically decorated just like the old Famous Dave’s. One never lacks for something interesting to look at. It’s very clean and spacious with everything you’d need in the kitchen. The host is very responsive and nice. The pontoon was excellent. Just wish there was more of a lake view for the price. You get a slice of view by the lovely fire pit. The landscaping and seating behind the lodge is also relaxing. All in all, a very nice place for a large family gathering. We had a great...
United States
Jenn R.
Northwoods Rustic Lodge steps away from Round Lake in Richardson Bay & Pontoon

11. Stylish Signature Lodge, nestled in the Forest, with Teal Lake views

Stylish Signature Lodge, nestled in the Forest, with Teal Lake views
Hayward
10.0 out of 10, Exceptional, (4 reviews)
"The property and location was beautiful."
United States
Scott M.
Stylish Signature Lodge, nestled in the Forest, with Teal Lake views
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.
Save an average of 15% on thousands of hotels when you're signed in

Where to stay near Winter

Winter, Wisconsin, is a charming vacation destination perfect for winter getaways. Experience the rustic feel of Wisconsin with stunning lake views and romantic scenery. Explore the outdoor adventures and cozy winter retreats that this quaint city and its surrounding areas have to offer.

Ojibwa

Discover Ojibwa, a charming destination perfectly suited for family and outdoor adventure travelers who will appreciate its scenic beauty and recreational opportunities. Nestled close to Lake Chippewa and Ojibwa State Park, this welcoming city offers a blend of nature and leisure, with a local casino and resort enhancing your stay. Located about 5 miles by car from Winter, Ojibwa makes for a smart hotel booking choice, providing a cozy base to explore the area’s attractions.

New Post

Experience the charm of New Post, an excellent hub for outdoor enthusiasts and families looking to embrace the natural beauty of Wisconsin. Nestled near Lake Chippewa and Campers Island, this village offers a perfect backdrop for recreation, relaxation, and romance. With its scenic trails, golf opportunities, and local landmarks like the Hunter Townhall, visitors can enjoy a rich blend of activities. New Post is about 10 miles from Winter, making it a smart choice for a memorable stay.

Radisson

If you are an outdoor enthusiast or a family traveler, look no further than Radisson, known for its stunning scenery and abundant recreational activities. This charming city features attractions like the Beverly Lake Wildlife Area and Ojibwa State Park, perfect for exploring nature and enjoying family fun. With its proximity to Winter, about 11 miles away, Radisson offers a smart choice for your stay, seamlessly blending adventure and relaxation in a picturesque setting.

Couderay

Couderay stands out as a prime spot for travelers seeking a family-friendly escape immersed in nature. With attractions like the Beverly Lake Wildlife Area, Lac Courte Oreilles, and Hauer Springs State Wildlife Management Area, visitors can enjoy outdoor adventures, scenic views, and romantic getaways. Located about 14 miles from Winter, Couderay offers easy access to these experiences, making it a smart choice for your next vacation. Enjoy all that this charming city has to offer!

Meadowbrook

Travelers visiting the area often choose Meadowbrook, especially families and outdoor enthusiasts seeking close proximity to nature and recreational activities. This charming village is a gateway to attractions like Lake Winter and Ojibwa State Park, perfect for weekend getaways or family adventures. With a friendly atmosphere and access to local venues such as the Winter Public Library, Meadowbrook offers a blend of relaxation and exploration. Located about 10 miles from Winter, it’s a smart choice for your vacation stay.

Stay near popular attractions in and around Winter

Nestled in the heart of nature, Winter, Wisconsin, offers a perfect getaway for outdoor enthusiasts and romantics alike. Explore serene lakes and scenic islands, and capture stunning Wisconsin photo ops while enjoying leisurely strolls by the Wisconsin River—a tranquil escape that rivals even the charm of New York.

Learn more about Winter

Snowmobilers and ice fishers flock to Winter's frozen lakes, where the Tuscobia State Trail offers prime access for winter sports enthusiasts. Warm up at the Winter Greenhouse with its tropical plants, then ask locals about nearby Flambeau River State Forest for summer kayaking adventures.

A snowy landscape with a red barn and a red shed.

Top Winter Hotel Reviews

More cheap stays in Winter

Hotels in Winter with star-rating

Find out more about Winter

Top reasons to visit Winter

  • Outdoor Adventure: Winter, Wisconsin, is a haven for outdoor enthusiasts, offering skiing, hiking, and beautiful lakes for year-round activities.
  • Scenic Beauty: Visitors can enjoy stunning landscapes and picturesque views, especially at the Hayward Lakefront and nearby state parks.
  • Romantic Getaways: The charming environment makes it an ideal spot for couples seeking a cozy escape amidst nature.
  • Pet-Friendly Accommodations: Winter offers a variety of cozy, inviting lodging options suitable for families and pets.
  • Winter Sports: Local ski resorts provide exciting winter sports opportunities, perfect for thrill-seekers.

Find great hotels in and around Winter

Discover the charm of Winter, Wisconsin, where a variety of lodging options await you, including cozy resorts and inviting lodges. Perfect for families and adventure seekers alike, these pet-friendly accommodations provide a welcoming atmosphere for all travelers. Whether you're searching for luxurious hotel rooms or the best spots to unwind after a day of exploration, Winter has something to offer everyone looking for the ideal getaway.

  • Upscale Accommodations with an Up North Location: This charming resort-style lodging in Winter, Wisconsin, boasts a perfect guest rating of 10.0. It invites travelers to enjoy a myriad of sports and recreational activities, including kayaking, right on-site or nearby. Visitors can unwind while indulging in entertainment options like television and taking in stunning waterfront views. With its budget-friendly pricing and upscale amenities, this accommodation is perfect for those looking to embrace the natural beauty of the North while enjoying modern comforts.
  • Upscale Accommodations with an Up North Location. With an impressive guest rating of 10.0, this family-friendly resort is designed to create memorable vacation experiences for guests of all ages. Located in Winter, it provides a welcoming atmosphere with amenities tailored specifically for children, including a foosball table, video games, and travel cribs. The property not only ensures fun for the little ones but also allows families to bond over shared activities and games, making it an excellent choice for your next family getaway in the North.
  • Live Oak Cabin - Cabin on the Chippewa Flowage within a Resort: Nestled 15 miles from Winter, the Live Oak Cabin is an idyllic escape for nature lovers, holding a perfect guest rating of 10.0. This cabin-style lodging offers easy access to various sports and recreational activities, including kayaking. Guests can enjoy cozy entertainment options like cable or satellite TV, making it a comfortable retreat after a day spent exploring the great outdoors. Experience the tranquility of the Chippewa Flowage while enjoying the rustic charm of this cabin resort.

Where to stay near Winter

Winter, Wisconsin, is an outdoor lover's paradise, offering stunning scenery and romantic getaways. Explore the picturesque Hayward Lakefront for breathtaking views and endless adventure opportunities. With its charming winter retreats, Winter is perfect for family vacations or a cozy escape. Enjoy the crisp winter air and discover the best spots for a memorable Wisconsin winter vacation amidst the serene landscapes.

  • Ojibwa: Situated 5 miles from Winter, Ojibwa is a charming city that offers a delightful escape into nature. With its scenic landscapes and serene lakes, it's a perfect destination for outdoor enthusiasts and couples seeking a romantic getaway. The travel experience is enhanced by a variety of recreational areas, resorts, and campgrounds that cater to visitors year-round. Peak travel months from July to September bring a lively atmosphere, while quieter periods in March to April and December offer a more tranquil experience. Local highlights include the stunning natural state park and picturesque town neighborhoods, making Ojibwa a must-visit for those looking to connect with the outdoors.
  • New Post: Located 10 miles from Winter, New Post is a quaint village that captures the essence of rural Wisconsin. Known for its captivating scenery, this destination is ideal for travelers seeking outdoor adventures and romantic experiences. Visitors can explore hiking trails and recreational areas, all while enjoying the peaceful surroundings. The travel experience is vibrant during peak months from July to September, with a more relaxed vibe in March to April and December. Notable attractions include the nearby lake and the village's charming town hall, providing a wonderful backdrop for both relaxation and exploration.
  • Couderay: About 14 miles from Winter, Couderay is a lively city that welcomes visitors with its year-round outdoor activities and stunning scenery. While it sees peak travel in January and June to July, it remains a great destination for those seeking a romantic escape or an adventure-filled trip at any time of year. Popular activities include golf and access to recreational areas, ensuring that visitors have plenty of options for fun. Local attractions like the beautiful lake and national state park enrich the travel experience, making Couderay a fantastic choice for nature lovers and adventurers alike.

Things to do in Winter

Winter, Wisconsin, offers a perfect getaway for outdoor enthusiasts and couples seeking a romantic escape. Enjoy winter sports at local ski resorts, explore scenic trails for hiking adventures, and take advantage of the recreational areas. Golf lovers can also find opportunities to play amidst beautiful landscapes. Whether you’re hitting the slopes or enjoying nature, Winter provides a delightful mix of activities for an unforgettable vacation.

Shopping

In Winter, you can explore local shops for unique gifts and souvenirs. If you're up for a drive, visit the nearby Phillips Plaza, offering a variety of retail options, or head to the Hayward Shopping Center for more extensive shopping experiences.

Recreation

In Winter, Wisconsin, enjoy rejuvenating treatments at the Northwoods Spa, where natural ingredients enhance your wellness experience. For recreation, explore the stunning hiking trails in the Chequamegon National Forest, or unwind with fishing and kayaking on the serene Flambeau River, immersing yourself in nature's tranquility.

Adventure

Experience the thrill of snowmobiling on scenic trails around Winter, Wisconsin, where you can explore beautiful winter landscapes. For a unique adventure, try ice fishing on one of the local lakes, enjoying the peaceful surroundings while waiting for a catch.

Nightlife

Explore the laid-back vibe at The Rustic Tavern, where you can enjoy local brews and friendly conversation. For a lively night, visit The Winter Dance Hall for live music and dancing, immersing yourself in the community's spirit and rhythm.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Winter

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Winter are April and November to December, where the prices are slightly lower. This is in comparison to June to August, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Winter is Tuesday. The most expensive day to stay in Winter is Thursday.
  • Find cheap hotels on Expedia: Utilize Expedia’s search tool to narrow down your options based on your budget, preferred location, and the type of hotel you’re looking for. To find the most affordable prices and special offers, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your winter hotel reservations with your flights and activities through an Expedia package.

Find the best attractions in and around Winter

Winter, Wisconsin offers a perfect backdrop for outdoor enthusiasts and romantic getaways, featuring beautiful lakes, scenic islands, and nearby state parks. Visitors can enjoy a variety of attractions that highlight the area's stunning natural beauty, making it an ideal spot for those seeking adventure, relaxation, and picturesque views. Whether you're looking to explore the great outdoors or simply unwind by the water, Winter has something for everyone.

  • Ojibwa State Park: Located a mere 3 miles from Winter, Ojibwa State Park offers breathtaking scenery and a wealth of outdoor adventures. Visitors can explore hiking trails, enjoy picnicking spots, and immerse themselves in nature's beauty, perfect for those looking to unwind or seek adventure.
  • Lake Winter: Situated within Winter, Lake Winter is a serene destination for beach lovers and romantics alike. With its picturesque views and outdoor activities, it's an ideal spot for swimming, fishing, or simply relaxing by the water's edge.
  • Headflyer Island: Just 8 miles from Winter, Headflyer Island is a tranquil getaway. This island boasts beautiful beaches and outdoor activities, making it a perfect place for a day of exploration or relaxation surrounded by nature.

Best time to go to Winter

The best time to visit Winter can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Winter falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Winter falls in January, visitor numbers are average and weather is very cloudy with no rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January12.0°F (-11.1°C)No RainVery CloudyAverageAverage
February14.2°F (-9.9°C)No RainVery CloudySlightly LowAverage
March28.4°F (-2.0°C)Light RainMostly CloudySlightly LowAverage
April39.2°F (4.0°C)Light RainMostly CloudyAverageSlightly Low
May54.1°F (12.3°C)Light RainMostly SunnyAverageAverage
June64.0°F (17.8°C)Light RainMostly SunnySlightly HighSlightly High
July68.5°F (20.3°C)Light RainMostly SunnySlightly HighSlightly High
August66.4°F (19.1°C)Light RainMostly SunnySlightly HighSlightly High
September59.0°F (15.0°C)Light RainMostly SunnyAverageAverage
October45.0°F (7.2°C)Light RainMostly CloudySlightly LowAverage
November31.3°F (-0.4°C)Light RainMostly CloudyAverageSlightly Low
December18.7°F (-7.4°C)Light RainMostly CloudyAverageSlightly Low

The nearest major airports for your trip to Winter

To visit Winter, Wisconsin, you have several airport options. Duluth International Airport (DLH) is located 90 miles away, with nearby hotels like Fitger's Inn and Pier B Resort, both 5 miles from the airport, offering various transportation services. Mosinee Airport (CWA) is 97 miles away, featuring hotels such as Jefferson Street Inn and Holiday Inn & Suites Wausau-Rothschild, both 6 miles from the airport. EAU Claire Airport (EAU) is the closest at 70 miles, with hotel options like The Lismore Eau Claire, just 4 miles from the airport. All these hotels provide accessible transportation to their respective airports, ensuring a smooth travel experience.

Frequently asked questions

What is the best area to stay in Winter?
The best area to stay in Winter, Wisconsin, is directly within the town of Winter itself, particularly near Main Street, for convenient access to local amenities and the surrounding natural attractions.

Winter's Main Street area offers a central location with easy access to local shops, eateries, and essential services. This small town is a gateway to the region's extensive outdoor activities, including numerous lakes and trails. For those who appreciate a quiet, less crowded setting, Winter provides a relaxing base.

Families will find Winter a good fit due to its proximity to outdoor recreational opportunities. Nearby lakes like Lake Winter and Barker Lake offer fishing, boating, and swimming, while the local trails are excellent for hiking and exploring nature. The slower pace of the town allows families to enjoy quality time together without the distractions of a larger city.

Couples looking for a peaceful retreat will also enjoy staying in Winter. The area provides opportunities for quiet walks, scenic drives, and enjoying the natural beauty of northern Wisconsin.
What are the best family hotels in Winter?
For the best family-friendly hotels in Winter, consider the highly-rated "Upscale Accommodations" with an "Up North" location. and Hunter Lake Lodge awaits....

The "Upscale Accommodations" with an "Up North" location., boasting a superb 10.0 rating, is an excellent choice for families. This accommodation offers a range of family-focused amenities including books and games for children, a travel crib, a playground, and an outdoor play area. It also features a full kitchen, along with a porch, lanai, deck, patio, or balcony for outdoor enjoyment. Conveniently, the Flambeau River is just over 18 miles away.

Another outstanding option is Hunter Lake Lodge awaits..., which also holds a superb 10.0 rating. This lodge provides children's books, games, and toys, ensuring plenty of entertainment for younger guests. Its lake view and site location directly on a lake are ideal for families looking to enjoy water activities. The lodge is located less than 2 miles from Barker Lake and approximately 17 miles from the Chequamegon National Forest. Find more child-friendly accommodations in Winter
What are the most romantic hotels in Winter for couples?
For a romantic getaway in Winter, Wisconsin, consider the luxurious Hunter Lake Lodge.

Hunter Lake Lodge, with a superb 10.0 review rating, offers stunning lake views and is equipped with a full kitchen, a patio, a porch or lanai, and a deck or patio, providing ample space for relaxation. It is conveniently located near Barker Lake, just 1.8 miles away, and the expansive Chequamegon National Forest, 17.2 miles from the property.
What are the best hotels in Winter near Flambeau River?
For accommodations near the Flambeau River in Winter, two excellent options are available: Hunter Lake Lodge and Upscale Accommodations with an Up North location.

Hunter Lake Lodge, boasting a great 10.0 review rating, offers a wonderful lake view and is conveniently situated near Barker Lake, just 1.8 miles away. This lodge is particularly well-suited for families, providing books, games, and toys specifically for children.

Another highly-rated choice, also with a great 10.0 review score, is Upscale Accommodations with an Up North location. This lodging is located 18.2 miles from the Flambeau River. It is designed with families in mind, featuring a playground, an outdoor play area for children, and a travel crib. Additionally, guests can enjoy a full kitchen, a porch or lanai, a deck or patio, and a balcony or patio for relaxation.
When is the best time to go to Winter?
The best time to go to Winter, Wisconsin, depends on the activities you're interested in, with distinct seasons offering different experiences.

For those seeking classic winter activities, the months of December through March are ideal. During this period, the area is typically covered in snow, making it great for snowmobiling on the extensive trail system, cross-country skiing, and ice fishing on the many frozen lakes. Expect cold temperatures and the full winter wonderland experience.

If you prefer warmer weather and outdoor recreation, the summer months from June through August are excellent. This is the prime time for fishing, boating, and swimming in the area's lakes and rivers. Hiking and biking trails are also fully accessible, offering opportunities to explore the natural beauty.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Winter.
How much is the nightly rate at a Winter hotel?
Prices for hotels in Winter often vary, but you can find a great deal from $92 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

Explore a world of travel with Expedia