Winter Vacation Rentals

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Vacation Rentals in Winter

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

9.0 out of 10, Wonderful, (22)
"Owner made the check in process a breeze. Quaint and great spot in a nice location, definitely will be staying again. Thank you Bucktail Lodge! "
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

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

10.0 out of 10, Exceptional, (63)
"Very nice property, lovely location, easy communication."
5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.

EAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River

10.0 out of 10, Exceptional, (16)
"Beautiful views, beautiful cabins. Great resort bar that is always full of fun people. "
EAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River

Bucktail Lodge Lakeview Cabin on Barker Lake in Winter, Wisconsin

8.8 out of 10, Excellent, (5)
"Loved our stay at Bucktail Lodge! So beautiful. "
Bucktail Lodge Lakeview Cabin on Barker Lake in Winter, Wisconsin

Amazing Sunsets, Peaceful, Well Maintained Lake home on Beautiful, Barker lake

9.8 out of 10, Exceptional, (58)
"Nice place! We had a wonderful experience, would definitely come back some day!"
Amazing Sunsets, Peaceful, Well Maintained Lake home on Beautiful, Barker lake

Telemark Northwoods Lodging

3.5 star property
9.0 out of 10, Wonderful, (297)
"Perfect lodging option in a wonderful location."
The price is CA $204
CA $224 total
includes taxes & fees
Aug 28 - Aug 29
Telemark Northwoods Lodging

Round Lake Cabin Retreat

9.4 out of 10, Exceptional, (69)
"Loves the location and beautiful Round Lake! Our family could all be together and relax with plenty of space!"
Round Lake Cabin Retreat

Hayward, Round Lake Retreat! Private dock, 3 kayaks, beautifully maintained!

10.0 out of 10, Exceptional, (67)
"Loved our stay for Birkie weekend!"
Hayward, Round Lake Retreat! Private dock, 3 kayaks, beautifully maintained!

A-frame Cabin w/ Private Boat Dock!

3.0 star property
A-frame Cabin w/ Private Boat Dock!

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

9.6 out of 10, Exceptional, (199)
"It would be difficult to find a cottage with a better lake view than this one. It's our second time here and we love it. Very comfortable in every respect."
The price is CA $148
CA $429 total
includes taxes & fees
Sep 3 - Sep 4
Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!

Executive Custom Log Lodge on Little Round Lake

10.0 out of 10, Exceptional, (99)
"Great space, well organized. So many options for things to do together as a family. Our large family of 22 people make it an annual trip there. It perfect for us"
Executive Custom Log Lodge on Little Round Lake

500' Lakeshore, 2 Docks, Sand Beach, Sleeps 10, A/C, Pontoon Boat for Rent

9.8 out of 10, Exceptional, (61)
"We had a wonderful time during our stay. The home was excellent for a large family. The waterfront was amazing with a great shoreline."
500' Lakeshore, 2 Docks, Sand Beach, Sleeps 10, A/C, Pontoon Boat for Rent

Modern Cabin located between Grindstone and Lac Courte Oreilles

10.0 out of 10, Exceptional, (69)
"This property was PERFECTION. Highly recommend and so grateful! "
Modern Cabin located between Grindstone and Lac Courte Oreilles

The Getaway on Grindstone Lake

10.0 out of 10, Exceptional, (13)
"Great location in the heart of lake country. Cabin is a on the shore of Grindstone lake facing west for excellent views of the sunset."
The Getaway on Grindstone Lake

A Little Piece of Scandinavia In The North Woods, Spider Lake Chain, Hayward, WI

10.0 out of 10, Exceptional, (76)
"We had a great experience with this rental and the owners. The property had everything you need for your stay-all I’m great condition."
A Little Piece of Scandinavia In The North Woods, Spider Lake Chain, Hayward, WI

Round Lake Hideaway

9.0 out of 10, Wonderful, (29)
"Location was great; the kayaks and paddle boards were very nice. The living room furniture could use an upgrade .Overall it was a wonderful family trip!"
Round Lake Hideaway

Breezy Bay Beach On Round Lake

10.0 out of 10, Exceptional, (58)
"Beautiful place to stay."
Breezy Bay Beach On Round Lake

Moose Lake Hayward WI

2.0 star property
10.0 out of 10, Exceptional, (6)
"Our first time staying here. Perfect cabin for our weekend of fishing. Wish we had booked a couple more days. Walleye fishing was excellent. We will be back."
Moose Lake Hayward WI

Cabin on peaceful soo lake, phillips wi. Enjoy waking up in the great northwood

9.2 out of 10, Wonderful, (7)
"Enjoyed "
Cabin on peaceful soo lake, phillips wi. Enjoy waking up in the great northwood

Rustic cabin getaway on the shore of Soo Lake in Phillips, WI

8.6 out of 10, Excellent, (10)
"Great view from this 1900s cabin"
Rustic cabin getaway on the shore of Soo Lake in Phillips, WI
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

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, cottages, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winter vacation rentals we have selected for you start as low as CA $148 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 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?

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 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. 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.