Winter Vacation Rentals from ￥38,798: Search Short-Term Rentals

Q: What's the top vacation rental in Winter?

Bears Den on the private lake : This Winter vacation home rental is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

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Our top choices for Winter vacation rentals

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

Hayward

Tom N.

￥31,110 total

includes taxes & fees

Sep 1 - Sep 2

2. Chip-Wa Lodging Room 4

Hunter

Sandra B.

￥25,620 total

includes taxes & fees

Aug 2 - Aug 3

3. Secluded Riverfront Cabin | Hot Tub + Starlink

Ojibwa

Dan P.

￥112,892 total

includes taxes & fees

Aug 16 - Aug 17

Coffee/tea maker, fridge, microwave, oven

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

Hawkins

Robin

￥24,079 total

includes taxes & fees

Aug 2 - Aug 3

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

Hayward

Michael H.

￥72,682 total

includes taxes & fees

Aug 9 - Aug 10

Deluxe Suite, 1 Bedroom, Kitchen | Terrace/patio

6. Telemark Northwoods Lodging

Cable

Ruth

￥53,082 total

includes taxes & fees

Aug 2 - Aug 3

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

Hayward

Chelsie H.

8. 2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

Hayward

Shelli H.

￥36,325 total

includes taxes & fees

Sep 1 - Sep 2

9. Chip-Wa Lodging Room 6

Hunter

Kathy

￥25,620 total

includes taxes & fees

Aug 5 - Aug 6

10. Chip-Wa Lodging Room 1

Hunter

Thane B.

￥25,620 total

includes taxes & fees

Aug 5 - Aug 6

11. Rustic campground in Butternut

Butternut

￥10,794 total

includes taxes & fees

Aug 2 - Aug 3

12. Chip-Wa Lodging Room 5

Hunter

Heather

￥25,620 total

includes taxes & fees

Aug 2 - Aug 3

13. Red Pines - Elk Lake Efficiency #6A

Phillips

Karan B.

￥37,029 total

includes taxes & fees

Aug 2 - Aug 3

14. Chip-Wa Lodging Room 3

Hunter

￥25,620 total

includes taxes & fees

Aug 8 - Aug 9

15. River's Edge Tiny Home | Expansive Deck

Park Falls

Dan O.

￥84,305 total

includes taxes & fees

Aug 6 - Aug 7

2 bedrooms, desk, iron/ironing board, WiFi (free)

16. Ultimate Hayward Trailhead Cabin

Hayward

￥47,689 total

includes taxes & fees

Sep 1 - Sep 2

17. Granny's Nest

Conrath

￥28,812 total

includes taxes & fees

Aug 3 - Aug 4

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

Phillips

Dina A.

￥38,798 total

includes taxes & fees

Aug 10 - Aug 11

19. Lakefront Cabin on LCO - The Sunset Escape

Hayward

Jeffrey T.

￥116,517 total

includes taxes & fees

Sep 1 - Sep 2

20. 15min to trailhead, King Bed, PacMan

Hayward

Kevin K.

￥108,573 total

includes taxes & fees

Aug 3 - Aug 4

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Top Winter Hotel Reviews

Holiday Inn Express & Suites Hayward by IHG

8/10 Good

"Some of breakfast items were lukewarm at best. Warm them up some. Otherwise everything else wad great!"

Timber Inn

10/10 Excellent

"When I first stayed at the Timber Inn years ago, it was a nice little place to rest your head. Coming back now under the new ownership, I can honestly say the transformation is incredible. You can tell the new owners truly care about the property and about the people who stay there. The renovations they are making give the motel a fresh, welcoming feel while still keeping the small-town charm that makes it special. Of course, no trip of mine would be complete without a little adventure. Within minutes of checking in, my klutzy self managed to trip on the step into my room and injure my big toe. Thankfully, my pride was hurt more than anything else, and it definitely wasn’t the motel’s fault—just me proving once again that I’m my own biggest hazard! Despite my less-than-graceful entrance, my stay was wonderful. The rooms were clean, comfortable, and you can see the pride and hard work being poured into every improvement. The owners were friendly, welcoming, and genuinely invested in making guests feel at home. If you’re looking for a place to stay in Phillips, Wisconsin, I highly recommend giving the Timber Inn a try. I can’t wait to come back and see all the future improvements. Keep up the amazing work—you’ve brought new life to a place that already held a special spot in my heart!"

Northern Lights Inn

10/10 Excellent

"The staff was super friendly and helpful. It was clean a mostly quiet. There were people outside our window making a ruckus in the middle of the night. There was fresh fruit in the breakfast nook, which I appreciate as a diabetic who can’t have all the carbs. It was mostly clean, but we found garbage under one of the beds. We were offered plenty of towels, soap, and shampoo. We enjoyed all of the facilities: the fitness center, the pool, the hot tub, the arcade, and the bowling alley. We felt safe and were able to sleep well. The location was within walking distance of stores, restaurants, and gas stations."

Charming 2-bedroom Hayward Cabin on Lac Courte Oreilles

10/10 Excellent

"Cute little place with beautiful lakeshore that was definitely the highlight of our stay! The host was friendly, responsive, and communicated well throughout our visit. We really enjoyed our time and Love Hayward and specifically LCO!"

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

10/10 Excellent

"We had a great 2 night stay for a guys weekend of fishing and golf. The cabin was exactly what we needed. It has everything you need and more. A/C cooled the cabin well, the beds were comfortable, and the cabin was good and clean.When you stay make sure to stop in to the bucktail bar and grill and have a burger! Great food and service!"

Find out more about Winter

Search for holiday rentals in Winter on Expedia! You can easily find your home rentals, villas, holiday apartments in Winter using one of the methods below:

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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?

Bears Den on the private lake: This Winter vacation home rental is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

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. Winter Town Hall and Ojibwa State Park 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.

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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. Secluded Riverfront Cabin | Hot Tub + Starlink

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

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

6. Telemark Northwoods Lodging

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

8. 2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

9. Chip-Wa Lodging Room 6

10. Chip-Wa Lodging Room 1

11. Rustic campground in Butternut

12. Chip-Wa Lodging Room 5

13. Red Pines - Elk Lake Efficiency #6A

14. Chip-Wa Lodging Room 3

15. River's Edge Tiny Home | Expansive Deck

16. Ultimate Hayward Trailhead Cabin

17. Granny's Nest

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

19. Lakefront Cabin on LCO - The Sunset Escape

20. 15min to trailhead, King Bed, PacMan

Find vacation rentals that suit your style

Top Winter Hotel Reviews

Holiday Inn Express & Suites Hayward by IHG

Timber Inn

Charming 5-bedroom cabin just outside Hayward near OO, Tiger Cat,and Spider Lake

Northern Lights Inn

Charming 2-bedroom Hayward Cabin on Lac Courte Oreilles

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

Water's Edge Retreat on Butternut Lake!

Bucktail Lodge Lakeview Cabin on Barker Lake in Winter, Wisconsin

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

Find out more about Winter

Frequently asked questions

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