Winter Vacation Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Winter vacation rentals

Terrace/patio

1. Secluded Riverfront Cabin | Hot Tub + Starlink

Secluded Riverfront Cabin | Hot Tub + Starlink
Ojibwa
10.0 out of 10, Exceptional, (48 reviews)
"We had such a good time! "
United States
Dan P.
The price is AED 1,994
AED 2,271 total
includes taxes & fees
28 Sep - 29 Sep
Secluded Riverfront Cabin | Hot Tub + Starlink
Interior

2. 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)
"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 AED 367
AED 503 total
includes taxes & fees
1 Oct - 2 Oct
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
WiFi, bed sheets

3. Chip-Wa Lodging Room 4

Chip-Wa Lodging Room 4
Hunter
10.0 out of 10, Exceptional, (2 reviews)
"Very good as far as the location. My buddies were camping there just down the road. Right now I am wounded after a surgery and didn’t feel well enough to camp or even use a trailer. This place has location and everything else!"
United States
Charles
The price is AED 422
AED 598 total
includes taxes & fees
27 Sep - 28 Sep
Chip-Wa Lodging Room 4
Living area

4. 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.
Renovated cabin on Lac Courte Oreilles Lake - minutes from trails!
Property grounds

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 AED 605
AED 1,981 total
includes taxes & fees
27 Sep - 28 Sep
Kavanagh Bay Resort|Hot Tub&Sauna #1
TV, fireplace

6. Lakefront Cabin on LCO - The Sunset Escape

Lakefront Cabin on LCO - The Sunset Escape
Hayward
9.0 out of 10, Wonderful, (8 reviews)
"Very comfortable and great view of the lake."
United States
Jeffrey T.
The price is AED 900
AED 2,049 total
includes taxes & fees
28 Sep - 29 Sep
Lakefront Cabin on LCO - The Sunset Escape
Deluxe Suite, 1 Bedroom, Kitchen | Terrace/patio

7. Telemark Northwoods Lodging

Telemark Northwoods Lodging
3.5 star property
Cable
9.0 out of 10, Wonderful, (327 reviews)
"Good staff"
United States
Adam
The price is AED 380
AED 967 total
includes taxes & fees
11 Oct - 12 Oct
Telemark Northwoods Lodging
Dining

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

Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!
Hayward
9.6 out of 10, Exceptional, (237 reviews)
"Wonderful cabin and quiet, beautiful area. We enjoyed our stay and would definitely stay again. "
United States
Eric Z.
The price is AED 559
AED 1,264 total
includes taxes & fees
28 Sep - 29 Sep
Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!
Interior

9. 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)
"Very quiet resort , cabin had everything we needed .. we enjoyed fishing and the golfing area. It’s an older cabin but very clean and comfortable beds"
United States
Chris f.
The price is AED 367
AED 503 total
includes taxes & fees
27 Sep - 28 Sep
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Coffee/tea maker, fridge, microwave, oven

10. 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, (29 reviews)
"Great hosts and location. "
United States
Paul H.
The price is AED 459
AED 562 total
includes taxes & fees
28 Sep - 29 Sep
Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.
Living area

11. 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, (18 reviews)
"Great place to getaway and be close to the water!"
United States
mark p.
The price is AED 760
AED 1,617 total
includes taxes & fees
19 Oct - 20 Oct
Lake Front Cabin, Media/Game Room, Kayaks, Multi-level deck--NEWLY REMODELED
Interior

12. Ultimate Hayward Trailhead Cabin

Ultimate Hayward Trailhead Cabin
Hayward
The price is AED 550
AED 1,050 total
includes taxes & fees
28 Sep - 29 Sep
Ultimate Hayward Trailhead Cabin
WiFi, bed sheets

13. Chip-Wa Lodging Room 6

Chip-Wa Lodging Room 6
Hunter
10.0 out of 10, Exceptional, (2 reviews)
"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
27 Sep - 28 Sep
Chip-Wa Lodging Room 6
WiFi, bed sheets

14. Chip-Wa Lodging Room 5

Chip-Wa Lodging Room 5
Hunter
10.0 out of 10, Exceptional, (2 reviews)
"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
27 Sep - 28 Sep
Chip-Wa Lodging Room 5
Exterior

15. 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, (78 reviews)
"Cute and cozy winter rental. Looks like it would be a great summer spot too!"
United States
David M.
The price is AED 479
AED 1,164 total
includes taxes & fees
2 Oct - 3 Oct
Blissful cozy, year round, lakeside cabin on Butternut Lake. Dogs welcome.
WiFi, bed sheets

16. 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
27 Sep - 28 Sep
Chip-Wa Lodging Room 1
Property grounds

17. 15min to trailhead, King Bed, PacMan

15min to trailhead, King Bed, PacMan
Hayward
9.6 out of 10, Exceptional, (14 reviews)
"It was a good long weekend the stay was enjoyable with good neighbors and relaxing accommodations "
United States
Kevin K.
The price is AED 1,621
AED 1,924 total
includes taxes & fees
4 Oct - 5 Oct
15min to trailhead, King Bed, PacMan
Interior

18. The Blue Musky Golf, UTV & Snowmobile Escape

The Blue Musky Golf, UTV & Snowmobile Escape
Hayward
10.0 out of 10, Exceptional, (23 reviews)
"Great spot right on the course, deck was a great spot to reminisce about the rounds"
United States
Jacob B.
The price is AED 574
AED 1,931 total
includes taxes & fees
8 Oct - 9 Oct
The Blue Musky Golf, UTV & Snowmobile Escape
Property grounds

19. 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, (37 reviews)
"Great place"
United States
Darla J.
The price is AED 661
AED 804 total
includes taxes & fees
27 Sep - 28 Sep
Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails
WiFi, bed sheets

20. 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
28 Sep - 29 Sep
Chip-Wa Lodging Room 2
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

Timber Inn

Timber Inn

8/10 Good
"New owners have remarkable turn things around looking pretty good after a lot of clean up"
Ron 1-night trip
Posted 4 days ago
Timber Inn

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 Lake Chippewa 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.