Winter Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Winter vacation rentals

A camping area with a table and chairs, surrounded by tall trees and a lake.

1. Telemark Northwoods Lodging

Telemark Northwoods Lodging
3.5 star property
Cable
9.0 out of 10, Wonderful, (331 reviews)
"Clean, quietā€¦easy check in. Great communication pre check-in. Beautiful setting/area. Will be backā€¦"
United States
Thomas
The price is SARĀ 338
SARĀ 370 total
includes taxes & fees
15 Nov - 16 Nov
Telemark Northwoods Lodging
A lakeside outdoor seating area with Adirondack chairs and a fire pit.

2. Secluded Riverfront Cabin | Hot Tub + Starlink

Secluded Riverfront Cabin | Hot Tub + Starlink
Ojibwa
10.0 out of 10, Exceptional, (50 reviews)
"We had such a good time! "
United States
Dan P.
The price is SARĀ 1,724
SARĀ 2,080 total
includes taxes & fees
18 Nov - 19 Nov
Secluded Riverfront Cabin | Hot Tub + Starlink
A grassy area with trees and a body of water.

3. 2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Hayward
9.2 out of 10, Wonderful, (26 reviews)
"We liked the property and the cabin was fine. Management was not available and there was no communication. The grounds were in need of up keep. The weather was tremendous. All in all we had a good stay because we are simple folks that know how to enjoy ourselves."
United States
Dawn
The price is SARĀ 375
SARĀ 481 total
includes taxes & fees
15 Nov - 16 Nov
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
A compact kitchen with wooden walls, a microwave, a coffee maker, and a trash bin.

4. Chip-Wa Lodging Room 1

Chip-Wa Lodging Room 1
Hunter
10.0 out of 10, Exceptional, (3 reviews)
"Enjoyed our stay. Cozy and quaint."
United States
Thane B.
The price is SARĀ 431
SARĀ 578 total
includes taxes & fees
15 Nov - 16 Nov
Chip-Wa Lodging Room 1
A circular outdoor seating area with Adirondack chairs and a fire pit, surrounded by a grassy lawn and a forested backdrop.

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

Kavanagh Bay Resort|Hot Tub&Sauna #1
Hayward
7.2 out of 10, Good, (5 reviews)
"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.
The price is SARĀ 624
SARĀ 2,067 total
includes taxes & fees
15 Nov - 16 Nov
Kavanagh Bay Resort|Hot Tub&Sauna #1
Interior

6. 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, (32 reviews)
"Great place, location and hosts. "
United States
Paul H.
The price is SARĀ 469
SARĀ 515 total
includes taxes & fees
15 Nov - 16 Nov
Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.
A view through a window of a grassy yard with a pond, trees, and a small building.

7. 2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Hayward
8.4 out of 10, Very good, (11 reviews)
"Cabin was perfect for our needs. Host met us and let us know the important information about the property and let us be. Would stay again."
United States
Katie L.
The price is SARĀ 375
SARĀ 481 total
includes taxes & fees
15 Nov - 16 Nov
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Outdoor seating with Adirondack chairs and a fire pit by a lake.

8. Blissful cozy, year round, lakeside cabin on Butternut Lake. Dogs welcome.

Blissful cozy, year round, lakeside cabin on Butternut Lake. Dogs welcome.
Butternut
10.0 out of 10, Exceptional, (82 reviews)
"Cute and cozy winter rental. Looks like it would be a great summer spot too!"
United States
David M.
The price is SARĀ 490
SARĀ 1,206 total
includes taxes & fees
15 Nov - 16 Nov
Blissful cozy, year round, lakeside cabin on Butternut Lake. Dogs welcome.
Interior

9. Ultimate Hayward Trailhead Cabin

Ultimate Hayward Trailhead Cabin
Hayward
10.0 out of 10, Exceptional, (1 review)
"My husband and I had a wonderful stay at this cabin. The pictures and description are totally accurate. The home was clean, well furnished and as comfortable as home including the beds. The kitchen was well equipped with everything we needed and the linnens were fresh, new and plush. The shower is spacious and there was plenty of hot water. The screened porch was wonderful to sit out in the afternoon and watch the leaves fall in the breeze. (We were there early October). We found lots of...
United States
Joan O.
The price is SARĀ 562
SARĀ 1,027 total
includes taxes & fees
16 Nov - 17 Nov
Ultimate Hayward Trailhead Cabin
A person holding a fish on a boat.

10. Renovated cabin on Lac Courte Oreilles Lake - minutes from trails!

Renovated cabin on Lac Courte Oreilles Lake - minutes from trails!
Northwoods Beach
10.0 out of 10, Exceptional, (26 reviews)
"Our second time staying and we love it! We especially enjoyed the addition of the front/lake facing deck "
United States
ANN M.
The price is SARĀ 709
SARĀ 1,251 total
includes taxes & fees
15 Nov - 16 Nov
Renovated cabin on Lac Courte Oreilles Lake - minutes from trails!
A log cabin with a fire pit and chairs in a wooded area.

11. Red Pines - Elk Lake Efficiency #6A

Red Pines - Elk Lake Efficiency #6A
Phillips
9.6 out of 10, Exceptional, (16 reviews)
"Nice room but the futon bed was tilting and not comfortable. Otherwise a good room and good value. Better for 2 people than 3."
United States
Reuben
The price is SARĀ 573
SARĀ 861 total
includes taxes & fees
15 Nov - 16 Nov
Red Pines - Elk Lake Efficiency #6A
A compact kitchenette with a microwave, coffee maker, and a small stool.

12. Chip-Wa Lodging Room 2

Chip-Wa Lodging Room 2
Hunter
8.0 out of 10, Very good, (2 reviews)
"Excellent for a short fishing trip or short stay! Smaller rooms without all the frills. Very clean and easy process to check in and out. Cost was acceptable for the value. If you are looking for a basic stay this is it. Excellent value and location for anyone whoā€™s experiencing the outdoors of the Northwoods. "
United States
Matthew
The price is SARĀ 363
SARĀ 471 total
includes taxes & fees
16 Nov - 17 Nov
Chip-Wa Lodging Room 2
A rustic cabin surrounded by dense forest.

13. 2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Hayward
8.4 out of 10, Very good, (20 reviews)
"Thank you for the great stay! I had everything I needed."
United States
Mark B.
The price is SARĀ 469
SARĀ 589 total
includes taxes & fees
18 Nov - 19 Nov
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
A wooden cabin with a porch, surrounded by trees with autumn foliage.

14. Lake Cabin Ā· Hot Tub Ā· Fire Pit Ā· Free Firewood

Lake Cabin Ā· Hot Tub Ā· Fire Pit Ā· Free Firewood
Hayward
9.8 out of 10, Exceptional, (25 reviews)
"the place is in good shape and the location is awesome. "
United States
Kevin R.
The price is SARĀ 1,108
SARĀ 2,774 total
includes taxes & fees
15 Nov - 16 Nov
Lake Cabin Ā· Hot Tub Ā· Fire Pit Ā· Free Firewood
A gravel driveway leading to a small, single-story building surrounded by dense trees and greenery.

15. Comfortable 3 Bedroom Cabin On the Shores of Lake Chippewa Flowage in Hayward WI

Comfortable 3 Bedroom Cabin On the Shores of Lake Chippewa Flowage in Hayward WI
Hayward
9.2 out of 10, Wonderful, (10 reviews)
"We felt like we we transported to the 60ā€™s. The atmosphere and ambiance fit. We had everything we needed and the management was great. If you want old school WI resort this is your place!"
United States
Nina H.
The price is SARĀ 751
SARĀ 937 total
includes taxes & fees
18 Nov - 19 Nov
Comfortable 3 Bedroom Cabin On the Shores of Lake Chippewa Flowage in Hayward WI
A residential property with a large evergreen tree, a house with a visible front porch, and a small garden area.

16. Cozy home in Wisconsin's recreational northwoods.

Cozy home in Wisconsin's recreational northwoods.
Butternut
7.6 out of 10, Good, (5 reviews)
"Weather was hot, fishing was difficult at best, we had a good time."
United States
Robert
The price is SARĀ 405
SARĀ 780 total
includes taxes & fees
15 Nov - 16 Nov
Cozy home in Wisconsin's recreational northwoods.
A grassy area with three blue chairs and a small table, overlooking a body of water and trees.

17. 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, (38 reviews)
"Great place"
United States
Darla J.
The price is SARĀ 676
SARĀ 805 total
includes taxes & fees
15 Nov - 16 Nov
Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails
A wooden staircase leading to a deck with a house in the background.

18. Motorsports Basecamp near lakes and forest

Motorsports Basecamp near lakes and forest
Hayward
9.8 out of 10, Exceptional, (34 reviews)
"Excellent host and accommodations."
United States
Ben S.
The price is SARĀ 530
SARĀ 1,168 total
includes taxes & fees
15 Nov - 16 Nov
Motorsports Basecamp near lakes and forest
A wooden cabin with a porch, a stone pillar, and a flag.

19. Hayward Basecamp Near Nelson Lake, Phipps Flowage & Downtown

Hayward Basecamp Near Nelson Lake, Phipps Flowage & Downtown
Hayward
Hayward Basecamp Near Nelson Lake, Phipps Flowage & Downtown
A wooden deck with a bench and chairs, surrounded by trees and a view of a lake.

20. Lakefront Cabin on LCO - The Sunset Escape

Lakefront Cabin on LCO - The Sunset Escape
Hayward
9.2 out of 10, Wonderful, (9 reviews)
"Very comfortable and great view of the lake."
United States
Jeffrey T.
The price is SARĀ 730
SARĀ 1,856 total
includes taxes & fees
17 Nov - 18 Nov
Lakefront Cabin on LCO - The Sunset Escape
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.
View all properties

Find vacation rentals that suit your style

cabin image
Cabins
Cabins
Apartment image
Apartments
Apartments

Top Winter Hotel Reviews

A two-story building with a stone chimney, large windows, and outdoor umbrellas.
Holiday Inn Express & Suites Hayward by IHG

Holiday Inn Express & Suites Hayward by IHG

Holiday Inn Express & Suites Hayward by IHG
Hayward

10/10 Excellent

I stayed here with my son and my husband, and we LOVED this place. Our room was really spacious: Two queen beds (which looked more like doubles, but who cares) and a separate L-shaped couch (which I assume had a sofa bed as well). You could definitely sleep a family of six in this room. The three of us had plenty of room to spread out. Our room was on the second floor and we had a balcony that had a view of Hayward Lake and a grove of birch trees. It was beautiful. We've stayed other places in...
United States
CARRIE
Reviewed November 18, 2016
Holiday Inn Express & Suites Hayward by IHG

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 11 Expedia vacation rentals in Winter for a memorable vacation.

What can I see and do in Winter?

Lake Winter and Barker Lake are a couple of lovely local spots to get outside and enjoy nature. Lake Chippewa and Chequamegon National Forest 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.