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

Winter Vacation Rentals

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Winter vacation rentals

A view through a window of a grassy yard with a lake, trees, and a small building.

1. 2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Hayward
9.4 out of 10, Exceptional, (23 reviews)
"Very quiet resort , cabin had everything we needed .. we enjoyed fishing and the golfing area. It’s an older cabin but very clean and comfortable beds"
United States
Chris f.
$125 nightly
The price is $137
Oct 4 - Oct 5
Total with taxes and fees
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
A room with two beds, a desk, a chair, and a window.

2. Chip-Wa Lodging Room 4

Chip-Wa Lodging Room 4
Hunter
10.0 out of 10, Exceptional, (2 reviews)
"Very good as far as the location. My buddies were camping there just down the road. Right now I am wounded after a surgery and didn’t feel well enough to camp or even use a trailer. This place has location and everything else!"
United States
Charles
$150 nightly
The price is $163
Sep 30 - Oct 1
Total with taxes and fees
Chip-Wa Lodging Room 4
Wildwood Escapes-Chippewa River Cabin is located 40 SE of Hayward, WI.

3. Secluded Riverfront Cabin | Hot Tub + Starlink

Secluded Riverfront Cabin | Hot Tub + Starlink
Ojibwa
10.0 out of 10, Exceptional, (48 reviews)
"We had such a good time! "
United States
Dan P.
$543 nightly
The price is $573
Oct 12 - Oct 13
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.

4. 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)
$125 nightly
The price is $137
Oct 1 - Oct 2
Total with taxes and fees
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
A wooden cabin interior with a large dining table, chairs, and a view of a lake through large windows.

5. 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, (237 reviews)
"Wonderful cabin and quiet, beautiful area. We enjoyed our stay and would definitely stay again. "
United States
Eric Z.
Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!
An outdoor seating area with Adirondack chairs and a fire pit, surrounded by a forested landscape.

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

Kavanagh Bay Resort|Hot Tub&Sauna #1
Hayward
7.2 out of 10, Good, (5 reviews)
"This host was amazing! The house was clean and exactly what we were looking for. The hot tub was warm and an awesome way to relax after a long day of snowmobiling. We definitely look forward to staying here again!!"
United States
Chelsie H.
$542 nightly
The price is $546
Sep 30 - Oct 1
Total with taxes and fees
Kavanagh Bay Resort|Hot Tub&Sauna #1
A wooden staircase leading to a deck with a house in the background.

7. 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.
$235 nightly
The price is $258
Sep 30 - Oct 1
Total with taxes and fees
Motorsports Basecamp near lakes and forest
Private kitchen

8. 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, (29 reviews)
"Great hosts and location. "
United States
Paul H.
$145 nightly
The price is $153
Sep 30 - Oct 1
Total with taxes and fees
Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.
A campsite with a trailer, a tent, and a car.

9. Rustic campground in Butternut

Rustic campground in Butternut
Butternut
$65 nightly
The price is $69
Sep 30 - Oct 1
Total with taxes and fees
Rustic campground in Butternut
A wooden deck with two wicker chairs and a table, overlooking a forest with autumn foliage.

10. Telemark Northwoods Lodging

Telemark Northwoods Lodging
3.5 star property
Cable
9.0 out of 10, Wonderful, (327 reviews)
"Good staff"
United States
Adam
$252 nightly
The price is $276
Oct 11 - Oct 12
Total with taxes and fees
Telemark Northwoods Lodging
A wooden cabin room with a nightstand, a lamp with a bear silhouette, a tissue box, and a remote control.

11. Chip-Wa Lodging Room 6

Chip-Wa Lodging Room 6
Hunter
10.0 out of 10, Exceptional, (2 reviews)
"Room was very clean. Property looks well kept and price was affordable."
United States
Kathy
$150 nightly
The price is $163
Sep 30 - Oct 1
Total with taxes and fees
Chip-Wa Lodging Room 6
Interior

12. Ultimate Hayward Trailhead Cabin

Ultimate Hayward Trailhead Cabin
Hayward
$270 nightly
The price is $286
Sep 30 - Oct 1
Total with taxes and fees
Ultimate Hayward Trailhead Cabin
A rustic log cabin with a green roof, a small porch, and a view of a lake.

13. Blissful cozy, year round, lakeside cabin on Butternut Lake. Dogs welcome.

Blissful cozy, year round, lakeside cabin on Butternut Lake. Dogs welcome.
Butternut
10.0 out of 10, Exceptional, (78 reviews)
"Cute and cozy winter rental. Looks like it would be a great summer spot too!"
United States
David M.
$301 nightly
The price is $317
Oct 2 - Oct 3
Total with taxes and fees
Blissful cozy, year round, lakeside cabin on Butternut Lake. Dogs welcome.
A wooden cabin bedroom with a bed, a nightstand, a lamp, a gray sofa, and a wooden door.

14. Chip-Wa Lodging Room 1

Chip-Wa Lodging Room 1
Hunter
10.0 out of 10, Exceptional, (3 reviews)
"Enjoyed our stay. Cozy and quaint."
United States
Thane B.
$150 nightly
The price is $163
Sep 30 - Oct 1
Total with taxes and fees
Chip-Wa Lodging Room 1
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.

15. 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 30 - Oct 1
Total with taxes and fees
Chip-Wa Lodging Room 5
A cozy living room with a fireplace, large windows, and a view of a lake.

16. 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, (18 reviews)
"Great place to getaway and be close to the water!"
United States
mark p.
$402 nightly
The price is $440
Oct 19 - Oct 20
Total with taxes and fees
Lake Front Cabin, Media/Game Room, Kayaks, Multi-level deck--NEWLY REMODELED
A living room with a wooden floor, a television mounted on the wall, a desk with a chair, a sofa, and a lamp.

17. Cozy home in Wisconsin's recreational northwoods.

Cozy home in Wisconsin's recreational northwoods.
Butternut
7.6 out of 10, Good, (5 reviews)
"Weather was hot, fishing was difficult at best, we had a good time."
United States
Robert
$215 nightly
The price is $227
Oct 2 - Oct 3
Total with taxes and fees
Cozy home in Wisconsin's recreational northwoods.
A spacious room with a large dining table, leather seating, and large windows offering a view.

18. The Blue Musky Golf, UTV & Snowmobile Escape

The Blue Musky Golf, UTV & Snowmobile Escape
Hayward
10.0 out of 10, Exceptional, (23 reviews)
"Great spot right on the course, deck was a great spot to reminisce about the rounds"
United States
Jacob B.
$465 nightly
The price is $509
Oct 8 - Oct 9
Total with taxes and fees
The Blue Musky Golf, UTV & Snowmobile Escape
A cozy log cabin interior with a wooden ceiling, a ceiling fan, a large arched window, a leather sofa, a coffee table, and a small side table.

19. Lakefront Cabin on LCO - The Sunset Escape

Lakefront Cabin on LCO - The Sunset Escape
Hayward
9.0 out of 10, Wonderful, (8 reviews)
"Very comfortable and great view of the lake."
United States
Jeffrey T.
$539 nightly
The price is $567
Oct 20 - Oct 21
Total with taxes and fees
Lakefront Cabin on LCO - The Sunset Escape
A room with two beds, a check-out sign, a lamp, and a painting on the wall.

20. Chip-Wa Lodging Room 2

Chip-Wa Lodging Room 2
Hunter
8.0 out of 10, Very good, (2 reviews)
"Excellent for a short fishing trip or short stay! Smaller rooms without all the frills. Very clean and easy process to check in and out. Cost was acceptable for the value. If you are looking for a basic stay this is it. Excellent value and location for anyone who’s experiencing the outdoors of the Northwoods. "
United States
Matthew
$150 nightly
The price is $163
Sep 30 - Oct 1
Total with taxes and fees
Chip-Wa Lodging Room 2
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Hotel Reviews

Timber Inn

Timber Inn

10/10 Excellent
"We had to cut our visit short. And when we turned in the key"
Amy 2-night trip
Posted 6 hours ago
Timber Inn

Find out more about Winter

Everything you need to know about Winter vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winter vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winter vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winter vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winter. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winter in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $276 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winter rentals

At Expedia, we put the best Winter vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winter rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winter vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winter. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Winter?

Yes, you can find vacation rentals near top attractions in Winter, or you can choose a more secluded option if you're looking for relaxation.

What's the top vacation rental in Winter?

5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.: Visitors give good reviews to this Winter vacation home rental, which is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games. Our travelers also rate Amazing Sunsets, Peaceful, Well Maintained Lake home on Beautiful, Barker lake as a favorite home for rent in Winter.

How many vacation rentals are there in Winter?

Choose from 11 Expedia vacation rentals in Winter for a memorable vacation.

What can I see and do in Winter?

Lake Winter and Barker Lake are a couple of lovely local spots to get outside and enjoy nature. Lake Chippewa and Chequamegon National Forest are other places to visit while you're in town.

What are vacation rentals like in Winter?

Vacation rentals are privately owned accommodations you can stay in for several days or longer in Winter. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for a small group gathering.