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

Winter Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Winter vacation rentals

A tray with breakfast items including eggs, bacon, and a muffin, a glass of orange juice, and a hot tub in the background.

1. Secluded Riverfront Cabin | Hot Tub + Starlink

Secluded Riverfront Cabin | Hot Tub + Starlink
Ojibwa
10.0 out of 10, Exceptional, (49 reviews)
"We had such a good time! "
United States
Dan P.
$512 nightly
The price is $540
Nov 8 - Nov 9
Total with taxes and fees
Secluded Riverfront Cabin | Hot Tub + Starlink
A wooden deck with two wicker chairs and a table, overlooking a forest with autumn foliage.

2. Telemark Northwoods Lodging

Telemark Northwoods Lodging
3.5 star property
Cable
9.0 out of 10, Wonderful, (331 reviews)
"Clean, quiet…easy check in. Great communication pre check-in. Beautiful setting/area. Will be back…"
United States
Thomas
$241 nightly
The price is $264
Nov 1 - Nov 2
Total with taxes and fees
Telemark Northwoods Lodging
A view through a window of a grassy yard with a pond, trees, and a small building.

3. 2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Hayward
8.4 out of 10, Very good, (11 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.
$117 nightly
The price is $128
Nov 1 - Nov 2
Total with taxes and fees
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
A cozy room with a bed, a sofa, a wooden wall, a door, and a small table with a lamp.

4. 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.
$142 nightly
The price is $154
Nov 1 - Nov 2
Total with taxes and fees
Chip-Wa Lodging Room 1
A view through a window of a grassy yard with a lake, trees, and a small building.

5. 2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Hayward
9.2 out of 10, Wonderful, (26 reviews)
"We liked the property and the cabin was fine. Management was not available and there was no communication. The grounds were in need of up keep. The weather was tremendous. All in all we had a good stay because we are simple folks that know how to enjoy ourselves."
United States
Dawn
$117 nightly
The price is $128
Nov 1 - Nov 2
Total with taxes and fees
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
A campsite with a trailer, a tent, and a car.

6. Rustic campground in Butternut

Rustic campground in Butternut
Butternut
$65 nightly
The price is $69
Nov 1 - Nov 2
Total with taxes and fees
Rustic campground in Butternut
An outdoor seating area with Adirondack chairs and a fire pit, surrounded by a forested landscape.

7. 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.
$547 nightly
The price is $551
Nov 1 - Nov 2
Total with taxes and fees
Kavanagh Bay Resort|Hot Tub&Sauna #1
A rustic log cabin with a green roof, a small porch, and a view of a lake.

8. 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, (79 reviews)
"Cute and cozy winter rental. Looks like it would be a great summer spot too!"
United States
David M.
$321 nightly
The price is $338
Nov 1 - Nov 2
Total with taxes and fees
Blissful cozy, year round, lakeside cabin on Butternut Lake. Dogs welcome.
A wooden cabin with a porch, surrounded by trees with autumn foliage.

9. Lake Cabin · Hot Tub · Fire Pit · Free Firewood

Lake Cabin · Hot Tub · Fire Pit · Free Firewood
Hayward
9.8 out of 10, Exceptional, (25 reviews)
"the place is in good shape and the location is awesome. "
United States
Kevin R.
$687 nightly
The price is $752
Nov 1 - Nov 2
Total with taxes and fees
Lake Cabin · Hot Tub · Fire Pit · Free Firewood
Private kitchen

10. 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, (30 reviews)
"Great place, location and hosts. "
United States
Paul H.
$145 nightly
The price is $153
Nov 1 - Nov 2
Total with taxes and fees
Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.
A spacious living area with a wooden floor, a sofa, a coffee table, and a kitchen area with a large window.

11. Renovated cabin on Lac Courte Oreilles Lake - minutes from trails!

Renovated cabin on Lac Courte Oreilles Lake - minutes from trails!
Northwoods Beach
10.0 out of 10, Exceptional, (26 reviews)
"Our second time staying and we love it! We especially enjoyed the addition of the front/lake facing deck "
United States
ANN M.
$314 nightly
The price is $333
Nov 3 - Nov 4
Total with taxes and fees
Renovated cabin on Lac Courte Oreilles Lake - minutes from trails!
A wooden staircase leading to a deck with a house in the background.

12. Motorsports Basecamp near lakes and forest

Motorsports Basecamp near lakes and forest
Hayward
9.8 out of 10, Exceptional, (34 reviews)
"Excellent host and accommodations."
United States
Ben S.
$258 nightly
The price is $283
Nov 1 - Nov 2
Total with taxes and fees
Motorsports Basecamp near lakes and forest
A living room with a wooden floor, a television mounted on the wall, a desk with a chair, a sofa, and a lamp.

13. 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
$220 nightly
The price is $232
Nov 1 - Nov 2
Total with taxes and fees
Cozy home in Wisconsin's recreational northwoods.
A log cabin with a fire pit and chairs in a wooded area.

14. Red Pines - Elk Lake Efficiency #6A

Red Pines - Elk Lake Efficiency #6A
Phillips
9.6 out of 10, Exceptional, (16 reviews)
"Nice room but the futon bed was tilting and not comfortable. Otherwise a good room and good value. Better for 2 people than 3."
United States
Reuben
$219 nightly
The price is $240
Nov 1 - Nov 2
Total with taxes and fees
Red Pines - Elk Lake Efficiency #6A
Interior

15. Ultimate Hayward Trailhead Cabin

Ultimate Hayward Trailhead Cabin
Hayward
10.0 out of 10, Exceptional, (1 review)
"My husband and I had a wonderful stay at this cabin. The pictures and description are totally accurate. The home was clean, well furnished and as comfortable as home including the beds. The kitchen was well equipped with everything we needed and the linnens were fresh, new and plush. The shower is spacious and there was plenty of hot water. The screened porch was wonderful to sit out in the afternoon and watch the leaves fall in the breeze. (We were there early October). We found lots of...
United States
Joan O.
$272 nightly
The price is $288
Nov 2 - Nov 3
Total with taxes and fees
Ultimate Hayward Trailhead Cabin
A wooden sauna with a sliding glass door, two white lanterns, and the text "sunlighters Amplify" on the glass.

16. Flambeau River Gem | Tiny Home w/Sauna

Flambeau River Gem | Tiny Home w/Sauna
Park Falls
9.8 out of 10, Exceptional, (12 reviews)
"Tina was a great communicator and the property was perfect for us. Highly recommend."
United States
Peggy C.
$405 nightly
The price is $445
Nov 2 - Nov 3
Total with taxes and fees
Flambeau River Gem | Tiny Home w/Sauna
A rustic cabin surrounded by dense forest.

17. 2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Hayward
8.4 out of 10, Very good, (20 reviews)
"Thank you for the great stay! I had everything I needed."
United States
Mark B.
$143 nightly
The price is $157
Nov 18 - Nov 19
Total with taxes and fees
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
A gravel driveway leading to a small, single-story building surrounded by dense trees and greenery.

18. Comfortable 3 Bedroom Cabin On the Shores of Lake Chippewa Flowage in Hayward WI

Comfortable 3 Bedroom Cabin On the Shores of Lake Chippewa Flowage in Hayward WI
Hayward
9.2 out of 10, Wonderful, (10 reviews)
"We felt like we we transported to the 60’s. The atmosphere and ambiance fit. We had everything we needed and the management was great. If you want old school WI resort this is your place!"
United States
Nina H.
$228 nightly
The price is $250
Nov 18 - Nov 19
Total with taxes and fees
Comfortable 3 Bedroom Cabin On the Shores of Lake Chippewa Flowage in Hayward WI
A wooden staircase with a handrail, a door leading to an outdoor area with a rocking chair, and a wooden floor inside.

19. Hayward Basecamp Near Nelson Lake, Phipps Flowage & Downtown

Hayward Basecamp Near Nelson Lake, Phipps Flowage & Downtown
Hayward
$479 nightly
The price is $482
Nov 2 - Nov 3
Total with taxes and fees
Hayward Basecamp Near Nelson Lake, Phipps Flowage & Downtown
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

Holiday Inn Express & Suites Hayward by IHG

Holiday Inn Express & Suites Hayward by IHG

10/10 Excellent
"From check in to check out the place was clean, beautiful room and delicious breakfast especially loved the cinnamon rolls and the fresh coffee"
Cynthia 1-night trip
Posted 12 hours ago
Holiday Inn Express & Suites Hayward by IHG

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 $215 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.