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

Winter Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Winter vacation rentals

Interior

1. 2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Hayward
9.4 out of 10, Exceptional, (23 reviews)
"Cabin was clean. Everything 2 guys needed for a few days fishing."
United States
Tom N.
The price is AED 551
AED 726 total
includes taxes & fees
2 Sep - 3 Sep
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Interior

2. Lunar Lodge on Windfall Lake

Lunar Lodge on Windfall Lake
Exeland
The price is AED 581
AED 2,267 total
includes taxes & fees
12 Aug - 13 Aug
Lunar Lodge on Windfall Lake
WiFi, bed sheets

3. Chip-Wa Lodging Room 6

Chip-Wa Lodging Room 6
Hunter
10.0 out of 10, Exceptional, (1 review)
"Room was very clean. Property looks well kept and price was affordable."
United States
Kathy
The price is AED 422
AED 598 total
includes taxes & fees
12 Aug - 13 Aug
Chip-Wa Lodging Room 6
Deluxe Suite, 1 Bedroom, Kitchen | Terrace/patio

4. Telemark Northwoods Lodging

Telemark Northwoods Lodging
3.5 star property
Cable
9.0 out of 10, Wonderful, (323 reviews)
"Great location for a fun Telemark event weekend."
United States
Ruth
The price is AED 413
AED 1,003 total
includes taxes & fees
12 Aug - 13 Aug
Telemark Northwoods Lodging
Coffee/tea maker, fridge, microwave, oven

5. 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, (25 reviews)
"Awesome place, very comfortable, quite surroundings! Very easy access from highway! Up north for family reunion! Will definitely stay again in the future!!"
United States
Robin
The price is AED 459
AED 562 total
includes taxes & fees
12 Aug - 13 Aug
Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.
Property grounds

6. Modern Cabin with Classic Northwoods Experience...Close to Trails

Modern Cabin with Classic Northwoods Experience...Close to Trails
Hayward
10.0 out of 10, Exceptional, (38 reviews)
"We enjoyed every single aspect of our stay. If you believe the description too good to be true, I can assure you it is even better than described. It’s magical."
United States
Richard (Ty) R.
The price is AED 694
AED 1,569 total
includes taxes & fees
8 Sep - 9 Sep
Modern Cabin with Classic Northwoods Experience...Close to Trails
Terrace/patio

7. Secluded Riverfront Cabin | Hot Tub + Starlink

Secluded Riverfront Cabin | Hot Tub + Starlink
Ojibwa
10.0 out of 10, Exceptional, (47 reviews)
"We had such a good time! "
United States
Dan P.
The price is AED 2,236
AED 2,696 total
includes taxes & fees
16 Aug - 17 Aug
Secluded Riverfront Cabin | Hot Tub + Starlink
Property grounds

8. Rustic campground in Butternut

Rustic campground in Butternut
Butternut
The price is AED 165
AED 252 total
includes taxes & fees
12 Aug - 13 Aug
Rustic campground in Butternut
WiFi, bed sheets

9. 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
The price is AED 422
AED 598 total
includes taxes & fees
12 Aug - 13 Aug
Chip-Wa Lodging Room 5
Property grounds

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

Kavanagh Bay Resort|Hot Tub&Sauna #1
Hayward
7.0 out of 10, Good, (2 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 AED 853
AED 2,418 total
includes taxes & fees
12 Aug - 13 Aug
Kavanagh Bay Resort|Hot Tub&Sauna #1
Interior

11. 2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Hayward
8.6 out of 10, Excellent, (10 reviews)
"Quiet resort. I really enjoyed spending time with my family and just getting away for a week."
United States
Shelli H.
The price is AED 643
AED 848 total
includes taxes & fees
1 Sep - 2 Sep
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
WiFi, bed sheets

12. Chip-Wa Lodging Room 4

Chip-Wa Lodging Room 4
Hunter
10.0 out of 10, Exceptional, (1 review)
"Property exactly as described. Room was clean, comfortable and priced right. We will be back!"
United States
Sandra B.
The price is AED 422
AED 598 total
includes taxes & fees
17 Aug - 18 Aug
Chip-Wa Lodging Room 4
Interior

13. Chip-Wa Lodging Room 3

Chip-Wa Lodging Room 3
Hunter
8.0 out of 10, Very Good, (1 review)
The price is AED 422
AED 598 total
includes taxes & fees
12 Aug - 13 Aug
Chip-Wa Lodging Room 3
2 bedrooms, desk, iron/ironing board, WiFi (free)

14. Ultimate Hayward Trailhead Cabin

Ultimate Hayward Trailhead Cabin
Hayward
The price is AED 579
AED 1,046 total
includes taxes & fees
1 Sep - 2 Sep
Ultimate Hayward Trailhead Cabin
WiFi, bed sheets

15. 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 AED 422
AED 598 total
includes taxes & fees
17 Aug - 18 Aug
Chip-Wa Lodging Room 1
Exterior detail

16. Granny's Nest

Granny's Nest
Conrath
8.0 out of 10, Very Good, (1 review)
The price is AED 380
AED 676 total
includes taxes & fees
12 Aug - 13 Aug
Granny's Nest
WiFi, bed sheets

17. 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 who’s experiencing the outdoors of the Northwoods. "
United States
Matthew
The price is AED 422
AED 598 total
includes taxes & fees
17 Aug - 18 Aug
Chip-Wa Lodging Room 2
Living area

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

Lake Front Cabin, Media/Game Room, Kayaks, Multi-level deck--NEWLY REMODELED
Hayward
10.0 out of 10, Exceptional, (14 reviews)
"Excellent property, exceptional hosts. "
United States
Michael H.
The price is AED 1,018
AED 2,020 total
includes taxes & fees
21 Aug - 22 Aug
Lake Front Cabin, Media/Game Room, Kayaks, Multi-level deck--NEWLY REMODELED
Property grounds

19. Red Pines - Elk Lake Efficiency #6A

Red Pines - Elk Lake Efficiency #6A
Phillips
9.6 out of 10, Exceptional, (13 reviews)
"Quiet, peaceful place that was perfect for a weekend getaway. The room was clean and well stocked. "
United States
Karan B.
The price is AED 514
AED 872 total
includes taxes & fees
16 Aug - 17 Aug
Red Pines - Elk Lake Efficiency #6A
Property grounds

20. 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.
The price is AED 661
AED 829 total
includes taxes & fees
24 Aug - 25 Aug
Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails
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
"Honestly, this is an elevated property that we thoroughly enjoyed!"
Tasha 2-night trip
Posted 14 hours ago
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 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. 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.