Winter Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Winter

Red Pines - Elk Lake #6A | Studio, 1 Bath

9.4 out of 10, Exceptional, (8)
"It was nice. Missed the sink in the bathroom, but for a quick stay, the kitchenette sink worked fine!"
Red Pines - Elk Lake #6A | Studio, 1 Bath

Tiny Home w/River Access | Sauna + Deck

9.6 out of 10, Exceptional, (5)
"Overall, very nice place to stay. Very peaceful and taken care of. Tina was very responsive. "
Tiny Home w/River Access | Sauna + Deck

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

2.0 star property
9.6 out of 10, Exceptional, (10)
"Was a nice and quiet place. Was very impressed with the place!!!!"
The price is NZ$256
includes taxes & fees
23 July - 24 July
Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails

Charming 2-bedroom house located in Ojibwa WI just off the Tuscobia Trail.

2.0 star property
10.0 out of 10, Exceptional, (5)
"Excellent home, clean, exactly as described. Right off Tuscobia Trail. Lovely!"
The price is NZ$330
includes taxes & fees
24 July - 25 July
Charming 2-bedroom house located in Ojibwa WI just off the Tuscobia Trail.

Lake Front, Arcade, Kayaks, Fire pit--NEWLY REMODELED Callahan's Shore Thing

10.0 out of 10, Exceptional, (3)
"A great little vacation spot! The kids had a blast fishing and kayaking. Abundant wildlife to see and plenty of restaurants in walking distance. "
The price is NZ$840
includes taxes & fees
3 Aug - 4 Aug
Lake Front, Arcade, Kayaks, Fire pit--NEWLY REMODELED Callahan's Shore Thing

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

10.0 out of 10, Exceptional, (16)
"Nice, cozy and clean cabin in a perfect location."
The price is NZ$925
includes taxes & fees
26 July - 27 July
Renovated cabin on Lac Courte Oreilles Lake - minutes from trails!

Birchwood Haven-Wooded Lakefront Cabin Retreat on Big Chetac Lake, Birchwood WI

10.0 out of 10, Exceptional, (12)
"A beautiful winter location and property. Spacious, inviting and comfortable home. Friendly, helpful and responsive hosts."
The price is NZ$1,748
includes taxes & fees
1 Aug - 2 Aug
Birchwood Haven-Wooded Lakefront Cabin Retreat on Big Chetac Lake, Birchwood WI
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winter Hotel Reviews

Frequently asked questions

Can I find a holiday rental in Winter?

Yes, there are holiday rentals close to the most popular sights in Winter, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winter has to offer?

500' Lakeshore, 2 Docks, Sand Beach, Sleeps 10, A/C, Pontoon Boat for Rent: This holiday home rental outside Winter is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Winter?

Choose from 13 Expedia holiday rentals in Winter for a memorable holiday.

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. Black Dan Lake and Chequamegon National Forest are other places to visit while you're in town.

What are holiday rentals like in Winter?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winter. Holiday rentals feature extras like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for a small group gathering.