Winter Vacation Rentals from $226: Search Short-Term Rentals

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Our top choices for Winter vacation rentals

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

Hayward

Chris f.

$125 nightly

Sep 21 - Sep 22

Total with taxes and fees

2. Chip-Wa Lodging Room 4

Hunter

Sandra B.

$150 nightly

Sep 20 - Sep 21

Total with taxes and fees

Deluxe Suite, 1 Bedroom, Kitchen | Terrace/patio

3. Telemark Northwoods Lodging

Cable

Ruth

$242 nightly

Sep 16 - Sep 17

Total with taxes and fees

4. Secluded Riverfront Cabin | Hot Tub + Starlink

Ojibwa

Dan P.

$588 nightly

Sep 20 - Sep 21

Total with taxes and fees

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

Hayward

mark p.

6. 2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

Hayward

Katie L.

$125 nightly

Sep 23 - Sep 24

Total with taxes and fees

7. Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!

Hayward

Eric Z.

$365 nightly

Sep 28 - Sep 29

Total with taxes and fees

8. Motorsports Basecamp near lakes and forest

Hayward

Chris P.

$246 nightly

Sep 16 - Sep 17

Total with taxes and fees

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

Hawkins

Robin

$145 nightly

Sep 16 - Sep 17

Total with taxes and fees

10. Lakefront Cabin on LCO - The Sunset Escape

Hayward

Jeffrey T.

$568 nightly

Sep 21 - Sep 22

Total with taxes and fees

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

Northwoods Beach

ANN M.

$407 nightly

Sep 24 - Sep 25

Total with taxes and fees

12. Ultimate Hayward Trailhead Cabin

Hayward

$257 nightly

Sep 16 - Sep 17

Total with taxes and fees

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

Butternut

David M.

$321 nightly

Sep 29 - Sep 30

Total with taxes and fees

14. Chip-Wa Lodging Room 5

Hunter

Heather

$150 nightly

Sep 17 - Sep 18

Total with taxes and fees

15. Red Pines - Elk Lake Efficiency #6A

Phillips

Karan B.

$216 nightly

Sep 17 - Sep 18

Total with taxes and fees

16. Chip-Wa Lodging Room 6

Hunter

Kathy

$150 nightly

Sep 16 - Sep 17

Total with taxes and fees

17. Chip-Wa Lodging Room 1

Hunter

Thane B.

$150 nightly

Sep 17 - Sep 18

Total with taxes and fees

18. Rustic campground in Butternut

Butternut

$65 nightly

Sep 17 - Sep 18

Total with taxes and fees

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

Phillips

Darla J.

$206 nightly

Sep 16 - Sep 17

Total with taxes and fees

20. Chip-Wa Lodging Room 2

Hunter

Matthew

$150 nightly

Sep 16 - Sep 17

Total with taxes and fees

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Top Winter Hotel Reviews

Holiday Inn Express & Suites Hayward by IHG

10/10 Excellent

"Beautiful woodsy style Holiday Inn located on the water. Fabulous!"

Quality Inn Ladysmith

10/10 Excellent

"Everything was just so cozy from the front office decor to the bed and bedding itself and the lighting by the bed when I walked into the room. The shower was relaxing and all amenities were available which was convenient that I didnt need to bring an iron with me and was able to make my first cup of coffee in the morning. The airiconditioning was nice and cool. The room was spacious. I watched a little TV before bed. I slept so very comfortably until my morning alarm! Easy and quick check out and super nice staff! I highly recommend staying here!"

Timber Inn

10/10 Excellent

"What a wonderful gem of a hotel! Very pretty setting with lakeview rooms. The rooms are spacious and super clean. Our room was newly renovated, and well designed (except no closet???). The staff is wonderful! Super friendly and knowledgeable about the area. Great morning breakfast. We would definitely stay here again!"

Charming 2-bedroom Hayward Cabin on Lac Courte Oreilles

10/10 Excellent

"Just a little fishing trip by myself. Very relaxing, fish didn’t cooperate but that’s fishing. If I’m still around next year I’ll be staying again. Brandon was very helpful when I couldn’t get the keurig machine to work, but there was another that he told me where it was, so had my coffee in the mornings. Everything else was fine."

5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.

10/10 Excellent

"What a wonderful home! The hosts are exceptional, they have thought of everything you could need to make your stay feel like home. Plenty of space for privacy for 8 guests. The kayaks where a huge hit, as was the game room on a rainy day. Beautiful sunsets, wildlife, and some good fishing off the pier. We will definitely be back!"

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 $226 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.

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Things to do in Northern Wisconsin

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 13 Expedia vacation rentals in Winter for a memorable vacation.

What can I see and do in Winter?

Lake Winter and Lake Chippewa are a couple of lovely local spots to get outside and enjoy nature. Chequamegon National Forest and Flambeau River 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.

Winter Vacation Rentals

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Check prices for these dates

Our top choices for Winter vacation rentals

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

2. Chip-Wa Lodging Room 4

3. Telemark Northwoods Lodging

4. Secluded Riverfront Cabin | Hot Tub + Starlink

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

6. 2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

7. Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!

8. Motorsports Basecamp near lakes and forest

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

10. Lakefront Cabin on LCO - The Sunset Escape

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

12. Ultimate Hayward Trailhead Cabin

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

14. Chip-Wa Lodging Room 5

15. Red Pines - Elk Lake Efficiency #6A

16. Chip-Wa Lodging Room 6

17. Chip-Wa Lodging Room 1

18. Rustic campground in Butternut

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

20. Chip-Wa Lodging Room 2

Find vacation rentals that suit your style

Top Winter Hotel Reviews

Holiday Inn Express & Suites Hayward by IHG

Find out more about Winter

Explore a world of travel with Expedia

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