Winter Vacation Rentals

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Our top choices for Winter vacation rentals

$65 nightly
The price is $69
Jan 29 - Jan 30
Total with taxes and fees
Rustic campground in Butternut
8.0 out of 10, Very Good, (4 reviews)
"Property was located just down the road from the snowmobiling trail and was easy and quick in/out access"
United States
Jake C.
$212 nightly
The price is $224
Jan 29 - Jan 30
Total with taxes and fees
Cozy home in Wisconsin's recreational northwoods.
9.4 out of 10, Exceptional, (10 reviews)
"Quiet, peaceful place that was perfect for a weekend getaway. The room was clean and well stocked. "
United States
Karan B.
$140 nightly
The price is $152
Jan 29 - Jan 30
Total with taxes and fees
Red Pines - Elk Lake #6A | Studio, 1 Bath
10.0 out of 10, Exceptional, (13 reviews)
"Clean and comfortable. "
United States
Shirley N.
$186 nightly
The price is $196
Jan 31 - Feb 1
Total with taxes and fees
Charming 2-bedroom house located in Ojibwa WI just off the Tuscobia Trail.
10.0 out of 10, Exceptional, (1 review)
"Great place to stay at. Host was accommodating. It was clean and cozy. I would book again"
United States
Nathan H.
$140 nightly
The price is $148
Feb 2 - Feb 3
Total with taxes and fees
The Bunkhouse, cozy studio in adorable Ladysmith. Escape to the Northwoods!
8.8 out of 10, Excellent, (27 reviews)
"Absolutely wonderful stay, very cabin like and rustic. Wished the TV worked for the kids at night, other than that, it was a great stay. "
United States
Crystal
$125 nightly
The price is $137
Feb 1 - Feb 2
Total with taxes and fees
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
9.8 out of 10, Exceptional, (20 reviews)
"Amazing place to stay! So convenient and affordable, always a pleasure to stay😊"
United States
Hannah
$145 nightly
The price is $153
Feb 1 - Feb 2
Total with taxes and fees
Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.
9.6 out of 10, Exceptional, (25 reviews)
"Very nice place enjoyed family time"
United States
Cheryl B.
$142 nightly
The price is $155
Jan 29 - Jan 30
Total with taxes and fees
Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails
10.0 out of 10, Exceptional, (76 reviews)
"Excellent stay. Loved the cabin. Very cutely decorated and clean. Host was very nice. "
United States
Rebecca P.
$317 nightly
The price is $334
Jan 29 - Jan 30
Total with taxes and fees
Blissful cozy, year round, lakeside cabin on Butternut Lake. Dogs welcome.
3.5 star property
9.0 out of 10, Wonderful, (316 reviews)
"Colors of the trees were beautiful, staff helpful, trails plentiful and walkable."
United States
Kenneth
$327 nightly
The price is $358
Jan 29 - Jan 30
Total with taxes and fees
Telemark Northwoods Lodging

Apartment in Hunter

Chip-Wa Lodging Room 6
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
Feb 1 - Feb 2
Total with taxes and fees
Chip-Wa Lodging Room 6
$460 nightly
The price is $463
Jan 29 - Jan 30
Total with taxes and fees
Lunar Lodge on Windfall Lake
9.6 out of 10, Exceptional, (4 reviews)
"We loved the house. It was exactly as pictured and described. The view was amazing. We sat on the dock one of the evenings we were there and watched the sunset. Beautiful! The house was very clean and well stocked with things we needed. "
United States
Kerri S.
$486 nightly
The price is $509
Feb 2 - Feb 3
Total with taxes and fees
Lakefront Cabin on LCO - The Sunset Escape
9.8 out of 10, Exceptional, (6 reviews)
"Super clean, friendly and great communication with property owner! "
United States
Kelly P.
$207 nightly
The price is $226
Feb 5 - Feb 6
Total with taxes and fees
Rock Garden Wisconsin Concrete Park | 3 Beds, comfortable and clean
10.0 out of 10, Exceptional, (13 reviews)
"Fantastic Place !!!!!! It was great and exactly what we needed!"
United States
Ryan
$193 nightly
The price is $209
Jan 29 - Jan 30
Total with taxes and fees
Red Pines - Elk Lake Condo #1 | 3 Bedroom, 1.5 Bath
10.0 out of 10, Exceptional, (4 reviews)
"Clean, comfortable, well furnished and roomy. Walkout access to the lake. "
United States
Matthew B.
$190 nightly
The price is $206
Feb 2 - Feb 3
Total with taxes and fees
Red Pines - Elk Lake Condo #6 | 3 Bed, 1 Bath
9.8 out of 10, Exceptional, (31 reviews)
"Wonderful accommodations. Great spot for a quick getaway!"
United States
Joe B.
$246 nightly
The price is $270
Jan 29 - Jan 30
Total with taxes and fees
Motorsports Basecamp near lakes and forest
10.0 out of 10, Exceptional, (8 reviews)
"Excellent property, exceptional hosts. "
United States
Michael H.
$329 nightly
The price is $360
Feb 22 - Feb 23
Total with taxes and fees
Lake Front Cabin, Media/Game Room, Connects to Trails--NEWLY REMODELED
$600 nightly
The price is $606
Feb 1 - Feb 2
Total with taxes and fees
Charming Northwoods Cabin Minutes from Hayward

Vacation Home in Ladysmith

Wiggle Weigel Lodges
9.6 out of 10, Exceptional, (4 reviews)
"Nice quiet area in a good location."
United Kingdom
Jeff R.
Wiggle Weigel Lodges
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.
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Top Winter Hotel Reviews

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 $155 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.

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?

Luxury 7,500‑Sq‑Ft Lakefront Lodge, Private Dock & Snowmobile Access: This vacation home near Winter is located on a lake and has a fireplace, a balcony, 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 can relax into your vacation with a garden and a selection of games.

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. Barker Lake and Black Dan Lake 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.