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

Best Resorts in Winter

Check prices for these dates

Next weekend
Sep 11 - Sep 13
In two weeks
Sep 18 - Sep 20
In one month
Oct 2 - Oct 4
In two months
Oct 30 - Nov 1
No exact matches found, but these alternatives could be just right

Recommended hotels in Winter

A covered outdoor seating area with Adirondack chairs and a view of a lake.

1. 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)
"This cabin is perfect for a group! The listing was exactly as described, beautiful property, and the lake is not busy. The host responds quickly and everything went great! "
United States
Jacqueline D.
$663 nightly
The price is $699
Sep 8 - Sep 9
Total with taxes and fees
The Lodge on Lake of the Pines - enjoy the Northwoods in comfort!
A hotel room with a large bed, a TV, a desk, a bathtub, and a window with a view of greenery.

2. AmericInn by Wyndham Ladysmith

AmericInn by Wyndham Ladysmith
3.0 star property
Ladysmith
8.2 out of 10, Very Good, (123 reviews)
"Room was comfortable and we appreciated the extras in the room; refrigerator, microwave, hair dryer and nice little closet for hanging clothes. Staff was very friendly and helpful. Breakfast item selection was better than expected for a continental breakfast. Will definitely stay there again."
United States
Tammie
$114 nightly
The price is $127
Sep 13 - Sep 14
Total with taxes and fees
AmericInn by Wyndham Ladysmith
A bedroom with a wooden sloped ceiling, a bed with a patterned bedspread, two bedside tables with lamps, and three framed pictures on the wall.

3. Timber Inn

Timber Inn
2.0 star property
Phillips
7.0 out of 10, Good, (328 reviews)
"My family and I had a wonderful stay at the Timber Inn! It is clear that the new owners are putting a lot of time and care into the space. The rooms were clean and comfortable, the amenities were thoughtful, and the staff extremely helpful. Would definitely stay here again when we're in the area!"
United States
Kelsey
$85 nightly
The price is $93
Sep 7 - Sep 8
Total with taxes and fees
Timber Inn
A hotel room with a large bed, two bedside tables, a chair, a wall-mounted air conditioner, and a framed picture.

4. AmeriVu Inn

AmeriVu Inn
2.0 star property
Park Falls
8.0 out of 10, Very Good, (399 reviews)
"Our room was extremely quiet and very clean. The staff was exceptional."
United States
Mark
$110 nightly
The price is $121
Oct 6 - Oct 7
Total with taxes and fees
AmeriVu Inn
A room with two beds, a desk, a chair, and a window.

5. Chip-Wa Lodging Room 4

Chip-Wa Lodging Room 4
Hunter
10.0 out of 10, Exceptional, (1 review)
"Property exactly as described. Room was clean, comfortable and priced right. We will be back!"
United States
Sandra B.
$150 nightly
The price is $163
Sep 7 - Sep 8
Total with taxes and fees
Chip-Wa Lodging Room 4
A dining area with multiple tables and chairs, a door with an exit sign, and a window with a view of the outside.

6. Super 8 by Wyndham Phillips

Super 8 by Wyndham Phillips
2.0 star property
Phillips
8.2 out of 10, Very Good, (284 reviews)
"Comfortable stay. Rooms were clean."
United States
Felicia
$91 nightly
The price is $100
Sep 14 - Sep 15
Total with taxes and fees
Super 8 by Wyndham Phillips
An indoor swimming pool with wooden beams, clear water, and a 30 ft depth marker.

7. Quality Inn Ladysmith

Quality Inn Ladysmith
2.5 star property
Ladysmith
8.6 out of 10, Excellent, (288 reviews)
"The staff is always very pleasant and personable."
United States
Jennifer
$102 nightly
The price is $114
Sep 27 - Sep 28
Total with taxes and fees
Quality Inn Ladysmith
A spacious lobby with a large window overlooking a lake, furnished with leather sofas and wooden tables, and featuring rustic decor including antler wall art.

8. Holiday Inn Express & Suites Hayward by IHG

Holiday Inn Express & Suites Hayward by IHG
2.5 star property
Hayward
9.6 out of 10, Exceptional, (712 reviews)
"Great accommodation"
United States
Ben
$175 nightly
The price is $192
Sep 13 - Sep 14
Total with taxes and fees
Holiday Inn Express & Suites Hayward by IHG
A modern kitchen with wooden cabinets, a built-in coffee machine, and a flat-screen TV.

9. Northern Lights Inn

Northern Lights Inn
2.5 star property
Park Falls
7.8 out of 10, Good, (230 reviews)
"Owner was friendly and would stay there again."
United States
Mattison
$117 nightly
The price is $129
Oct 1 - Oct 2
Total with taxes and fees
Northern Lights Inn
An outdoor seating area with Adirondack chairs and a fire pit, surrounded by a forested landscape.

10. Kavanagh Bay Resort|Hot Tub&Sauna #1

Kavanagh Bay Resort|Hot Tub&Sauna #1
Hayward
8.0 out of 10, Very Good, (3 reviews)
"Great place to stay!! Hot tub and sauna were great perks"
United States
Erica O.
$574 nightly
The price is $581
Sep 8 - Sep 9
Total with taxes and fees
Kavanagh Bay Resort|Hot Tub&Sauna #1
A wooden deck with two wicker chairs and a table, overlooking a forest with autumn foliage.

11. Telemark Northwoods Lodging

Telemark Northwoods Lodging
3.5 star property
Cable
9.0 out of 10, Wonderful, (324 reviews)
"Great location for a fun Telemark event weekend."
United States
Ruth
$214 nightly
The price is $235
Sep 15 - Sep 16
Total with taxes and fees
Telemark Northwoods Lodging

12. Secluded Riverfront Cabin | Hot Tub + Starlink

Secluded Riverfront Cabin | Hot Tub + Starlink
Ojibwa
10.0 out of 10, Exceptional, (47 reviews)
"We had such a good time! "
United States
Dan P.
$610 nightly
The price is $643
Sep 22 - Sep 23
Total with taxes and fees
Secluded Riverfront Cabin | Hot Tub + Starlink
A view through a window of a grassy yard with a pond, trees, and a small building.

13. 2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Hayward
8.6 out of 10, Excellent, (10 reviews)
"Cabin was perfect for our needs. Host met us and let us know the important information about the property and let us be. Would stay again."
United States
Katie L.
$125 nightly
The price is $137
Sep 23 - Sep 24
Total with taxes and fees
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
A wooden staircase leading to a deck with a house in the background.

14. Motorsports Basecamp near lakes and forest

Motorsports Basecamp near lakes and forest
Hayward
9.8 out of 10, Exceptional, (33 reviews)
"The place was clean and we enjoyed our stay. "
United States
Chris P.
Motorsports Basecamp near lakes and forest
A cozy living room with a fireplace, large windows, and a view of a lake.

15. Lake Front Cabin, Media/Game Room, Kayaks, Multi-level deck--NEWLY REMODELED

Lake Front Cabin, Media/Game Room, Kayaks, Multi-level deck--NEWLY REMODELED
Hayward
10.0 out of 10, Exceptional, (17 reviews)
"Great place to getaway and be close to the water!"
United States
mark p.
$412 nightly
The price is $451
Sep 28 - Sep 29
Total with taxes and fees
Lake Front Cabin, Media/Game Room, Kayaks, Multi-level deck--NEWLY REMODELED

16. Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.

Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.
Hawkins
10.0 out of 10, Exceptional, (28 reviews)
"Awesome place, very comfortable, quite surroundings! Very easy access from highway! Up north for family reunion! Will definitely stay again in the future!!"
United States
Robin
$145 nightly
The price is $153
Sep 7 - Sep 8
Total with taxes and fees
Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.
A wooden cabin interior with a large dining table, chairs, and a view of a lake through large windows.

17. 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
9.6 out of 10, Exceptional, (234 reviews)
"Wonderful cabin and quiet, beautiful area. We enjoyed our stay and would definitely stay again. "
United States
Eric Z.
$365 nightly
The price is $385
Sep 28 - Sep 29
Total with taxes and fees
Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!
A room with two beds, each with a quilted bedspread featuring a mountain and forest design. There is a painting of a mountain landscape on the wall, and a window with curtains on the left side.

18. Chip-Wa Lodging Room 5

Chip-Wa Lodging Room 5
Hunter
10.0 out of 10, Exceptional, (2 reviews)
"Place was defect for us. We are simple motel hotel people that want it clean, quiet, affordable. It was all of those things. And the owner was responsive and friendly and gave us the best recommendation for the perfect bar just around the corner. 😍"
United States
Heather
$150 nightly
The price is $163
Sep 7 - Sep 8
Total with taxes and fees
Chip-Wa Lodging Room 5
A wooden cabin room with a nightstand, a lamp with a bear silhouette, a tissue box, and a remote control.

19. Chip-Wa Lodging Room 6

Chip-Wa Lodging Room 6
Hunter
10.0 out of 10, Exceptional, (1 review)
"Room was very clean. Property looks well kept and price was affordable."
United States
Kathy
$150 nightly
The price is $163
Sep 7 - Sep 8
Total with taxes and fees
Chip-Wa Lodging Room 6
A campsite with a trailer, a tent, and a car.

20. Rustic campground in Butternut

Rustic campground in Butternut
Butternut
$65 nightly
The price is $69
Sep 7 - Sep 8
Total with taxes and fees
Rustic campground in Butternut
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.
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Top Winter Hotel Reviews

AmericInn by Wyndham Ladysmith

AmericInn by Wyndham Ladysmith

10/10 Excellent
"Yes"
Shane 3-night trip
Posted 3 hours ago
AmericInn by Wyndham Ladysmith

Find out more about Winter

Winter Resorts information

Number of reviews
2,238
Accommodation
6 Resorts
Lowest Price
$69
Highest Price
$699

Frequently asked questions

What can I expect from a resort vacation in Winter?
Longing for a relaxing getaway? Treat yourself to all the luxuries and comforts of a resort, where you can find everything you need for your vacation from tasty food and drink options to activities and shopping. Browse the resort options in the area and discover the one that's best for you, whether you see yourself kicking back in a suite with stunning views or hitting the golf course for an afternoon game.
What's a top resort in Winter?
Our highest-rated resorts around Winter: Enjoy 3 full-size units! Long Lake North – Luxury Lakeside Complex - Beach resort. 29.7 mi (47.7 km) from Winter. 3 bedroom Lakeside home, on Snowmobile & ATV trails. Pet friendly, onsite Dining - 31.6 mi (50.8 km) from Winter.
What can I do in Winter?
Lake Chippewa, Chequamegon National Forest, and Flambeau River are a few of the interesting sights to visit. Additional attractions in the area include Winter Town Hall and Lake Winter.
What's the weather like in Winter?
The hottest months are usually July and August with an average temp of 64°F, while the coldest months are January and February with an average of 18°F. The snowiest months in Winter are April, March, January, and February, with each month seeing an average of 10 inches of snowfall.

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