Holiday Rentals Winter from £165: Find Short-Term Rentals & Holiday Accommodations

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Our top choices for Winter holiday 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

Hayward

Chris f.

includes taxes & fees

21 Sept - 22 Sept

A room with two beds, a desk, a chair, and a window.

2. Chip-Wa Lodging Room 4

Hunter

Sandra B.

includes taxes & fees

15 Sept - 16 Sept

A wooden deck with two wicker chairs and a table, overlooking a forest with autumn foliage.

3. Telemark Northwoods Lodging

Cable

Ruth

includes taxes & fees

15 Sept - 16 Sept

4. Secluded Riverfront Cabin | Hot Tub + Starlink

Ojibwa

Dan P.

includes taxes & fees

22 Sept - 23 Sept

A cozy living room with a fireplace, large windows, and a view of a lake.

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

Hayward

mark p.

includes taxes & fees

7 Oct - 8 Oct

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

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

Hayward

Katie L.

includes taxes & fees

23 Sept - 24 Sept

A wooden cabin interior with a large dining table, chairs, and a view of a lake through large windows.

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

Hayward

Eric Z.

includes taxes & fees

28 Sept - 29 Sept

A wooden staircase leading to a deck with a house in the background.

8. Motorsports Basecamp near lakes and forest

Hayward

Chris P.

includes taxes & fees

15 Sept - 16 Sept

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Top Winter Hotel Reviews

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!"

Telemark Northwoods Lodging

10/10 Excellent

"We were so incredibly thankful to find such a lovely property to stay at in such short notice. we had planned to book in Ashland Wisconsin and found out that our booking was in Ashland Oregon. until we could get funds, transferred back appropriately with no place to stay on a busy Labor Day weekend. we were in a panic. if I said I cried, I mean ugly crying in the car with no place to go to. we found a soft place to land and collect ourselves. the first night was a beautiful stay and the second night and third night were spent at this property and we really truly enjoyed it. having the amenities of a full kitchen, a lovely balcony, a Jacuzzi and a fireplace with a separate bedroom and living quarters was exactly what our hearts needed after having such a eventful and stressful few days. the staff was friendly and nice and very accommodating,it was also so clean and well cared for . we didn't have to maneuver through shifting a bunch of our prior engagements or plans just some adjustments that after finding ourselves room less was inevitable. thank you for having us for allowing us to create beautiful memories together. we look forward to hopefully visiting again in the future!"

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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winter holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winter holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winter holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winter holiday rentals we have selected for you start as low as £165 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winter rentals

At Expedia, we put the best Winter holiday 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 holiday.

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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Rice Lake Holiday Rentals

Things to do in Northern Wisconsin

Frequently asked questions

Can I find a holiday rental in Winter?

Yes, there are holiday rentals close to the most popular sights in Winter, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winter has to offer?

5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.: This highly rated holiday home rental in Winter is located on a lake, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. Our travellers also rate Amazing Sunsets, Peaceful, Well Maintained Lake home on Beautiful, Barker lake as a favourite home for rent in Winter.

How many holiday rentals are there in Winter?

Choose from 13 Expedia holiday rentals in Winter for a memorable holiday.

What can I see and do in Winter?

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

What are holiday rentals like in Winter?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winter. Holiday rentals feature extras like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for a small group gathering.

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Check prices for these dates

Our top choices for Winter holiday 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 holiday rentals that suit your style

Top Winter Hotel Reviews

Quality Inn Ladysmith

Find out more about Winter

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