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

Winter Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Winter vacation rentals

Interior

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)
"Cabin was clean. Everything 2 guys needed for a few days fishing."
United States
Tom N.
$181 nightly
The price is $198
Sep 1 - Sep 2
Total with taxes and fees
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Interior

2. Lunar Lodge on Windfall Lake

Lunar Lodge on Windfall Lake
Exeland
$616 nightly
The price is $621
Aug 17 - Aug 18
Total with taxes and fees
Lunar Lodge on Windfall Lake
WiFi, bed sheets

3. 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
Aug 19 - Aug 20
Total with taxes and fees
Chip-Wa Lodging Room 6
Deluxe Suite, 1 Bedroom, Kitchen | Terrace/patio

4. Telemark Northwoods Lodging

Telemark Northwoods Lodging
3.5 star property
Cable
9.0 out of 10, Wonderful, (323 reviews)
"Great location for a fun Telemark event weekend."
United States
Ruth
$306 nightly
The price is $335
Aug 24 - Aug 25
Total with taxes and fees
Telemark Northwoods Lodging
Coffee/tea maker, fridge, microwave, oven

5. 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, (26 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
Aug 15 - Aug 16
Total with taxes and fees
Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.
Property grounds

6. Modern Cabin with Classic Northwoods Experience...Close to Trails

Modern Cabin with Classic Northwoods Experience...Close to Trails
Hayward
10.0 out of 10, Exceptional, (38 reviews)
"We enjoyed every single aspect of our stay. If you believe the description too good to be true, I can assure you it is even better than described. It’s magical."
United States
Richard (Ty) R.
$405 nightly
The price is $427
Sep 3 - Sep 4
Total with taxes and fees
Modern Cabin with Classic Northwoods Experience...Close to Trails
Terrace/patio

7. 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.
$666 nightly
The price is $703
Aug 16 - Aug 17
Total with taxes and fees
Secluded Riverfront Cabin | Hot Tub + Starlink
Property grounds

8. Rustic campground in Butternut

Rustic campground in Butternut
Butternut
$65 nightly
The price is $69
Aug 15 - Aug 16
Total with taxes and fees
Rustic campground in Butternut
WiFi, bed sheets

9. Chip-Wa Lodging Room 5

Chip-Wa Lodging Room 5
Hunter
10.0 out of 10, Exceptional, (1 review)
"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
Aug 17 - Aug 18
Total with taxes and fees
Chip-Wa Lodging Room 5
Property grounds

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

Kavanagh Bay Resort|Hot Tub&Sauna #1
Hayward
7.0 out of 10, Good, (2 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.
$653 nightly
The price is $661
Aug 19 - Aug 20
Total with taxes and fees
Kavanagh Bay Resort|Hot Tub&Sauna #1
Interior

11. 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)
"Quiet resort. I really enjoyed spending time with my family and just getting away for a week."
United States
Shelli H.
$211 nightly
The price is $231
Sep 2 - Sep 3
Total with taxes and fees
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
WiFi, bed sheets

12. 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
Aug 17 - Aug 18
Total with taxes and fees
Chip-Wa Lodging Room 4
Interior

13. Chip-Wa Lodging Room 3

Chip-Wa Lodging Room 3
Hunter
8.0 out of 10, Very Good, (1 review)
$150 nightly
The price is $163
Aug 17 - Aug 18
Total with taxes and fees
Chip-Wa Lodging Room 3
2 bedrooms, desk, iron/ironing board, WiFi (free)

14. Ultimate Hayward Trailhead Cabin

Ultimate Hayward Trailhead Cabin
Hayward
$267 nightly
The price is $285
Sep 1 - Sep 2
Total with taxes and fees
Ultimate Hayward Trailhead Cabin
WiFi, bed sheets

15. 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
Aug 17 - Aug 18
Total with taxes and fees
Chip-Wa Lodging Room 1
Exterior detail

16. Granny's Nest

Granny's Nest
Conrath
9.0 out of 10, Wonderful, (2 reviews)
"Was very nice and offered to accommodate"
United States
Nick V.
$176 nightly
The price is $185
Aug 15 - Aug 16
Total with taxes and fees
Granny's Nest
WiFi, bed sheets

17. 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
Aug 17 - Aug 18
Total with taxes and fees
Chip-Wa Lodging Room 2
Living area

18. 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, (14 reviews)
"Excellent property, exceptional hosts. "
United States
Michael H.
$502 nightly
The price is $550
Aug 21 - Aug 22
Total with taxes and fees
Lake Front Cabin, Media/Game Room, Kayaks, Multi-level deck--NEWLY REMODELED
Property grounds

19. Red Pines - Elk Lake Efficiency #6A

Red Pines - Elk Lake Efficiency #6A
Phillips
9.6 out of 10, Exceptional, (13 reviews)
"Quiet, peaceful place that was perfect for a weekend getaway. The room was clean and well stocked. "
United States
Karan B.
$217 nightly
The price is $237
Aug 16 - Aug 17
Total with taxes and fees
Red Pines - Elk Lake Efficiency #6A
Property grounds

20. Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails

Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails
Phillips
9.6 out of 10, Exceptional, (31 reviews)
"Very nice place to stay!"
United States
Dina A.
$206 nightly
The price is $226
Aug 24 - Aug 25
Total with taxes and fees
Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails
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

AmericInn by Wyndham Ladysmith

AmericInn by Wyndham Ladysmith

8/10 Good
"Clean quiet comfortable room. Breakfast was sufficient, and staff replenished food and supplies in a timely manner. One towel bar fell off the wall, and adjustable shower nozzle wouldn’t adjust. There usually was nobody at the front desk—there were instead instructions to use the phone provided to summon someone."
Joseph 2-night trip
Posted 2 days ago
AmericInn by Wyndham Ladysmith

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 $335 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 Bears Den on the private lake as a favorite home for rent in Winter.

How many vacation rentals are there in Winter?

Choose from 12 Expedia vacation rentals in Winter for a memorable vacation.

What can I see and do in Winter?

Lake Winter and Perch 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.