Winter Vacation Rentals from $332: Search Short-Term Rentals

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Our top choices for Winter vacation rentals

1. Chip-Wa Lodging Room 4

Hunter

Sandra B.

$150 nightly

Aug 2 - Aug 3

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

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

Hawkins

Robin

$145 nightly

Aug 1 - Aug 2

Total with taxes and fees

3. Motorsports Basecamp near lakes and forest

Hayward

Chris P.

Deluxe Suite, 1 Bedroom, Kitchen | Terrace/patio

4. Telemark Northwoods Lodging

Cable

Ruth

$304 nightly

Aug 5 - Aug 6

Total with taxes and fees

5. Chip-Wa Lodging Room 5

Hunter

Heather

$150 nightly

Aug 2 - Aug 3

Total with taxes and fees

6. Rustic campground in Butternut

Butternut

$65 nightly

Aug 1 - Aug 2

Total with taxes and fees

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

Hayward

Michael H.

$422 nightly

Aug 9 - Aug 10

Total with taxes and fees

8. Chip-Wa Lodging Room 6

Hunter

Kathy

$150 nightly

Aug 5 - Aug 6

Total with taxes and fees

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Top Winter Hotel Reviews

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!"

Holiday Inn Express & Suites Hayward by IHG

10/10 Excellent

"Absolutely beautiful setting. The lake view is serene and spacious. The lounge area is lovely and homey, and the breakfast is way above average. The rooms we had were very nice. We ate at River Deck restaurant which is a block away. The tuna nachos were superb."

The Lodge on Lake of the Pines - enjoy the Northwoods in comfort!

10/10 Excellent

"UTV trip, trail was right outside the entrance to property. Dustin was very easy to communicate with. We had 4 couples and each had their own bed and bathroom, it worked perfect. I also liked that there was seating for 8 in living room and around fire pit. This is a very cool place to stay. Everything was great."

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

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 $332 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 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. 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.

Winter Vacation Rentals

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Check prices for these dates

Our top choices for Winter vacation rentals

1. Chip-Wa Lodging Room 4

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

3. Motorsports Basecamp near lakes and forest

4. Telemark Northwoods Lodging

5. Chip-Wa Lodging Room 5

6. Rustic campground in Butternut

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

8. Chip-Wa Lodging Room 6

9. Chip-Wa Lodging Room 1

10. Granny's Nest

11. The Sylvan Chalet, Modern, Lakefront, Private, Refined, Close to Trails,

12. Red Pines - Elk Lake Efficiency #6A

13. Chip-Wa Lodging Room 3

14. River's Edge Tiny Home | Expansive Deck

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

16. Lakefront Cabin on LCO - The Sunset Escape

17. Lake Cabin · Hot Tub · Fire Pit · EV

18. Red Pines - Elk Lake Condo #1

19. Red Pines - Elk Lake Condo #3

Find vacation rentals that suit your style

Top Winter Hotel Reviews

Timber Inn

Find out more about Winter

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