Winter Vacation Rentals

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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 wooden deck with two wicker chairs and a table, overlooking a forest with autumn foliage.

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 AEDĀ 331
AEDĀ 362 total
includes taxes & fees
13 Nov - 14 Nov
Telemark Northwoods Lodging
Wildwood Escapes-Chippewa River Cabin is located 40 SE of Hayward, WI.

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 AEDĀ 1,699
AEDĀ 2,048 total
includes taxes & fees
18 Nov - 19 Nov
Secluded Riverfront Cabin | Hot Tub + Starlink
A view through a window of a grassy yard with a lake, trees, and a small building.

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 AEDĀ 367
AEDĀ 471 total
includes taxes & fees
15 Nov - 16 Nov
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
A wooden cabin bedroom with a bed, a nightstand, a lamp, a gray sofa, and a wooden door.

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 AEDĀ 422
AEDĀ 566 total
includes taxes & fees
13 Nov - 14 Nov
Chip-Wa Lodging Room 1
An outdoor seating area with Adirondack chairs and a fire pit, surrounded by a forested landscape.

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 AEDĀ 611
AEDĀ 2,023 total
includes taxes & fees
15 Nov - 16 Nov
Kavanagh Bay Resort|Hot Tub&Sauna #1
Private kitchen

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 AEDĀ 459
AEDĀ 531 total
includes taxes & fees
13 Nov - 14 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 AEDĀ 367
AEDĀ 471 total
includes taxes & fees
15 Nov - 16 Nov
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
A rustic log cabin with a green roof, a small porch, and a view of 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 AEDĀ 479
AEDĀ 1,180 total
includes taxes & fees
13 Nov - 14 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 AEDĀ 550
AEDĀ 1,058 total
includes taxes & fees
13 Nov - 14 Nov
Ultimate Hayward Trailhead Cabin
A spacious living area with a wooden floor, a sofa, a coffee table, and a kitchen area with a large window.

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 AEDĀ 694
AEDĀ 1,225 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 AEDĀ 600
AEDĀ 887 total
includes taxes & fees
13 Nov - 14 Nov
Red Pines - Elk Lake Efficiency #6A
A room with two beds, a check-out sign, a lamp, and a painting on the wall.

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 AEDĀ 356
AEDĀ 460 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 AEDĀ 459
AEDĀ 576 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 AEDĀ 1,084
AEDĀ 2,715 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 AEDĀ 735
AEDĀ 917 total
includes taxes & fees
18 Nov - 19 Nov
Comfortable 3 Bedroom Cabin On the Shores of Lake Chippewa Flowage in Hayward WI
A living room with a wooden floor, a television mounted on the wall, a desk with a chair, a sofa, and a lamp.

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 AEDĀ 419
AEDĀ 791 total
includes taxes & fees
13 Nov - 14 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 AEDĀ 661
AEDĀ 788 total
includes taxes & fees
13 Nov - 14 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 AEDĀ 519
AEDĀ 1,143 total
includes taxes & fees
15 Nov - 16 Nov
Motorsports Basecamp near lakes and forest
A wooden staircase with a handrail, a door leading to an outdoor area with a rocking chair, and a wooden floor inside.

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

Hayward Basecamp Near Nelson Lake, Phipps Flowage & Downtown
Hayward
The price is AEDĀ 703
AEDĀ 1,771 total
includes taxes & fees
14 Nov - 15 Nov
Hayward Basecamp Near Nelson Lake, Phipps Flowage & Downtown
A cozy log cabin interior with a wooden ceiling, a ceiling fan, a large arched window, a leather sofa, a coffee table, and a small side table.

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 AEDĀ 702
AEDĀ 1,804 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.
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Top Winter Hotel Reviews

A spacious lobby with a large window overlooking a lake, furnished with leather sofas and wooden tables, and featuring rustic decor including antler wall art.
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.