A snowy landscape with a red barn and a red shed.

Winter Vacation Rentals

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  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Winter vacation rentals

Fridge, microwave, oven, stovetop

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

Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.
Hawkins
10.0 out of 10, Exceptional, (22 reviews)
"Great hosts and location. "
United States
Paul H.
$145 nightly
The price is $153
Jul 12 - Jul 13
Total with taxes and fees
Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.
Property grounds

Red Pines - Elk Lake Efficiency #6A

Red Pines - Elk Lake Efficiency #6A
Phillips
9.6 out of 10, Exceptional, (12 reviews)
"Quiet, peaceful place that was perfect for a weekend getaway. The room was clean and well stocked. "
United States
Karan B.
$216 nightly
The price is $236
Jul 9 - Jul 10
Total with taxes and fees
Red Pines - Elk Lake Efficiency #6A
Smart TV

Cozy home in Wisconsin's recreational northwoods.

Cozy home in Wisconsin's recreational northwoods.
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.
$222 nightly
The price is $234
Jul 9 - Jul 10
Total with taxes and fees
Cozy home in Wisconsin's recreational northwoods.
Property grounds

Rustic campground in Butternut

Rustic campground in Butternut
Butternut
$65 nightly
The price is $69
Jul 9 - Jul 10
Total with taxes and fees
Rustic campground in Butternut
Deluxe Suite, 1 Bedroom, Kitchen | Terrace/patio

Telemark Northwoods Lodging

Telemark Northwoods Lodging
3.5 star property
Cable
9.0 out of 10, Wonderful, (321 reviews)
"Great location for a fun Telemark event weekend."
United States
Ruth
$317 nightly
The price is $347
Jul 13 - Jul 14
Total with taxes and fees
Telemark Northwoods Lodging
Exterior detail

Granny's Nest

Granny's Nest
Conrath
$175 nightly
The price is $184
Jul 9 - Jul 10
Total with taxes and fees
Granny's Nest
Interior

Chip-Wa Lodging Room 3

Chip-Wa Lodging Room 3
Hunter
8.0 out of 10, Very Good, (1 review)
$150 nightly
The price is $163
Jul 12 - Jul 13
Total with taxes and fees
Chip-Wa Lodging Room 3
Property grounds

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

Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails
Phillips
9.6 out of 10, Exceptional, (31 reviews)
"Very nice place to stay!"
United States
Dina A.
$246 nightly
The price is $269
Jul 9 - Jul 10
Total with taxes and fees
Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails
Property grounds

Kavanagh Bay Resort|Hot Tub&Sauna #1

Kavanagh Bay Resort|Hot Tub&Sauna #1
Hayward
10.0 out of 10, Exceptional, (1 review)
"This host was amazing! The house was clean and exactly what we were looking for. The hot tub was warm and an awesome way to relax after a long day of snowmobiling. We definitely look forward to staying here again!!"
United States
Chelsie H.
$585 nightly
The price is $592
Jul 13 - Jul 14
Total with taxes and fees
Kavanagh Bay Resort|Hot Tub&Sauna #1
TV, fireplace

Northwoods Escape: Lakeside Retreat w/ Deck

Northwoods Escape: Lakeside Retreat w/ Deck
Stone Lake
10.0 out of 10, Exceptional, (3 reviews)
"We rented this property for our relatives visiting from Sweden. They were very happy with the accomadations."
United States
Jean C.
$554 nightly
The price is $583
Aug 1 - Aug 2
Total with taxes and fees
Northwoods Escape: Lakeside Retreat w/ Deck
TV, fireplace

Lakefront Cabin on LCO - The Sunset Escape

Lakefront Cabin on LCO - The Sunset Escape
Hayward
9.6 out of 10, Exceptional, (5 reviews)
"Very comfortable and great view of the lake."
United States
Jeffrey T.
$714 nightly
The price is $758
Jul 14 - Jul 15
Total with taxes and fees
Lakefront Cabin on LCO - The Sunset Escape
Interior

Red Pines - Elk Lake Condo #1

Red Pines - Elk Lake Condo #1
Phillips
10.0 out of 10, Exceptional, (15 reviews)
"The property was just what we needed for our weekend trip. Everything was nice and clean."
United States
Tom B.
$274 nightly
The price is $300
Jul 19 - Jul 20
Total with taxes and fees
Red Pines - Elk Lake Condo #1
Property grounds

Lake Cabin · Hot Tub · Fire Pit · EV

Lake Cabin · Hot Tub · Fire Pit · EV
Hayward
9.8 out of 10, Exceptional, (22 reviews)
"Nice cabin, great beds. Really enjoyed our time. "
United States
Katie J.
$1,107 nightly
The price is $1,212
Jul 15 - Jul 16
Total with taxes and fees
Lake Cabin · Hot Tub · Fire Pit · EV
Fridge, microwave, oven, stovetop

The Red Walleye: A Big Home on Big Fish Golf Course - Sleeps 22!

The Red Walleye: A Big Home on Big Fish Golf Course - Sleeps 22!
Hayward
10.0 out of 10, Exceptional, (17 reviews)
"Wonderful property, very clean fit our needs of the group. Will definitely stay again"
United States
Kylene O.
$1,140 nightly
The price is $1,249
Jul 13 - Jul 14
Total with taxes and fees
The Red Walleye: A Big Home on Big Fish Golf Course - Sleeps 22!
House (4 Bedrooms) | Interior

Northwoods Escape: Lakeside Retreat w/ Deck

Northwoods Escape: Lakeside Retreat w/ Deck
3.0 star property
Stone Lake
$542 nightly
The price is $571
Aug 1 - Aug 2
Total with taxes and fees
Northwoods Escape: Lakeside Retreat w/ Deck
Terrace/patio

Secluded Riverfront Cabin | Hot Tub + Starlink

Secluded Riverfront Cabin | Hot Tub + Starlink
Ojibwa
10.0 out of 10, Exceptional, (47 reviews)
"This cabin was a perfect fit for our family of five and our dog. Everything was clean and comfortable, and the hot tub was a highlight of our stay. The location made it easy to get on the snowmobile trails, and the hosts were wonderful to work with and very responsive."
United States
Jennifer P.
$891 nightly
The price is $940
Aug 2 - Aug 3
Total with taxes and fees
Secluded Riverfront Cabin | Hot Tub + Starlink
Property grounds

Red Pines - Elk Lake Condo #2

Red Pines - Elk Lake Condo #2
Phillips
10.0 out of 10, Exceptional, (3 reviews)
"Great location"
United States
Sara S.
$273 nightly
The price is $299
Jul 9 - Jul 10
Total with taxes and fees
Red Pines - Elk Lake Condo #2
WiFi, bed sheets

Chip-Wa Lodging Room 5

Chip-Wa Lodging Room 5
Hunter
10.0 out of 10, Exceptional, (1 review)
"Place was defect for us. We are simple motel hotel people that want it clean, quiet, affordable. It was all of those things. And the owner was responsive and friendly and gave us the best recommendation for the perfect bar just around the corner. 😍"
United States
Heather
$150 nightly
The price is $163
Jul 9 - Jul 10
Total with taxes and fees
Chip-Wa Lodging Room 5
Property grounds

Red Pines - Elk Lake Condo #4

Red Pines - Elk Lake Condo #4
Phillips
10.0 out of 10, Exceptional, (3 reviews)
"We had a very short stay but it was great from check-in to check-out. Great communication, extremely clean and very cozy. A true Northwoods experience!"
United States
Rachel K.
$273 nightly
The price is $299
Jul 12 - Jul 13
Total with taxes and fees
Red Pines - Elk Lake Condo #4
Property grounds

15min to trailhead, King Bed, PacMan

15min to trailhead, King Bed, PacMan
Hayward
9.6 out of 10, Exceptional, (12 reviews)
"It was a good long weekend the stay was enjoyable with good neighbors and relaxing accommodations "
United States
Kevin K.
$638 nightly
The price is $698
Jul 28 - Jul 29
Total with taxes and fees
15min to trailhead, King Bed, PacMan
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

Holiday Inn Express & Suites Hayward by IHG

Holiday Inn Express & Suites Hayward by IHG

10/10 Excellent
"Great staff. Back side has lake views. Property has lake front shore line. Great breakfast. Good location in Hayward for access to lakes and downtown."
John 4-night trip
Posted 5 hours ago
Holiday Inn Express & Suites Hayward by IHG

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 $347 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.

Explore a world of travel with Expedia

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. Ojibwa State Park 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.