Holiday houses in Winter

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Winter

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost

Home in Ironwood Township

5 out of 5 average rating, 4 reviews

Top Notch

Top Notch is the perfect vacation home for multiple families or multi-generational use. It offers 1 bedroom and 1 bathroom on the lower level, 1 bedroom and 1 bathroom on the main level and 2 bedrooms and 1 bathroom on the upper level. The lower level also offers a family room with a brick fireplace and foosball table as well as a room leading off with an indoor hot tub. *The hot tub is open from Dec. 1 - April 1 only.* The main level has a large living room with a large stone fireplace, the adj

Guest favourite

Apartment in Ironwood

4.76 out of 5 average rating, 55 reviews

Spring Promo - Minimalist living at its finest !

An unforgettable smaller apt packs a punch for its size, hotel quality Perfect for single person or couple or traveling nurse to renew and relax, fishing, wateskiing or snowmobiling. Dual power leather recliner with power lumbar back support & headrests for movie night on 55" HD Samsung Smart TV Note: We request a picture on your profile and if you have limited or no ratings may request photo ID and greater information, also please add names of other guests as well if applicable when booking

Top Guest favourite

Cabin in Spooner

5 out of 5 average rating, 62 reviews

Lake front luxury! Hot tub, relax, swim, sun, fun!

Welcome to the Wooden Spoon Lodge. Relax with the whole family or group at this peaceful place to stay. Located on Big McKenzie this beautiful log cabin offers a gentle grade to the lake, fantastic fishing, and a private beach. The perfect place to create memories with your family and friends! Please see my YouTube channel Wendy Gimpel Realty Group for a walkthrough video. We have a boat lift if you wish to use you are welcome to. We have Kayak's and canoe for you to use and a row boat!

Guest favourite

Loft in Iron River

4.92 out of 5 average rating, 61 reviews

Waterfront Glass Treehouse. 5* Amenities. Woof!

A warm welcome to the Pike Lake Chain and the Glass Tree house. With so many 5 star reviews, we think the Tree House is most accurately described by our guests. Please, read the reviews of what a wonderful place you have found. ***Inclusive with all stays a terrific, exclusive, luxury, wine and cheese cruise aboard the Lady Joanne. Luxury amenities include plush robes/slippers, morning Caribou coffee and select bath salts, herbs. Fully outfitted fishing boat BTH. Dock Space available.

Guest favourite

Apartment in Hurley

4.89 out of 5 average rating, 47 reviews

Hurley: location for all hobbies, holidays, events

Your family will be close to everything when you stay at this centrally-located place. Two bedroom rental unit with large parking area in back for trucks and trailers 2 queen beds 1 sectional couch -1 block from silver street with many food and bar options. -On the ATV/ snowmobile trail -2 blocks from Iron Belle walking trail -Many cross country ski trails nearby -blackjack/Indianhead ski resort 13 miles. -Whitecap Mountain ski resort 13 miles - Powderhorn ski resort 10 miles.

Guest favourite

Chalet in Bessemer

4.95 out of 5 average rating, 247 reviews

Hot Tub • Fireplace • Dog Friendly •Big Powderhorn

My place is located at Big Powderhorn Ski Resort and close to Lake Superior, family-friendly activities, great views, restaurants and dining. You’ll love my place because of the location, the ambiance, the outdoor space, and the neighborhood. My place is good for couples, solo adventurers, and families (with kids). Dog friendly! Outdoor Hot Tub! Wood burning Fireplace with wood supplied! Great cell service! TV, Cable, Roku, WIFI....great entertainment! Washer/Dryer

Superhost

Condo in Bessemer

4.9 out of 5 average rating, 10 reviews

Ski In/Out BunkHouse at Black River Basin, Unit #1

Ski in/Ski out condo on Black River Basin Mtn. Spacious living areas and bedroom, with full kitchen and full bathroom. Fast WiFi, sauna, cable, ski lockers, and fireplace (wood provided). Great area all year round, especially for skiers and snowmobilers. Close to many waterfalls, hikes, and about 30 mins from Lake Superior. Also about a 5 minute drive to Jackson creek summit, which is another ski hill available with your pass. No pets, no smoking

Top Guest favourite

Cabin in Hayward

4.98 out of 5 average rating, 49 reviews

Charming Cabin right on Round Lk in Richardson Bay

Rustic, cozy cabin in Richardson Bay on 3,000 acre Round Lake. The cabin porch is about 50 feet from the lake! 2016 21' Bennington 90 HP pontoon included with all summer rentals. Three bedrooms with three queen beds. Two story loft, two bath with Jacuzzi tub in loft, two gas fireplaces, fully furnished 3 season porch, and central air/heating. This cabin lacks nothing for supplies! Just bring your clothes and fun! It is completely furnished!

Guest favourite

Chalet in Wakefield

4.85 out of 5 average rating, 118 reviews

Indianhead Red Lodge by Ski Resort

We are offering our vacation home to rent. It is located right down the road from Indianhead Ski Resort. Our favorite place to be! 1500 sq ft of room to spread out. A perfect rental for a large family, a couple families, or adult time away without the kids. The property sits on 5 acres of wooded land scattered with seasonal wildflowers. The property has plenty of room to park snowmobile/ATV trailers. The trails are close by.

Guest favourite

Home in Danbury

4.93 out of 5 average rating, 29 reviews

Hangar House-Near the Clubhouse and Airstrip

Located across the street from the Clubhouse and the Airstrip, you won’t find a better location for your next vacation! Step out the front door and enjoy the area’s best 18-hole golf course. You’ll also find a bar and restaurant, indoor pool and fitness center, pickle ball court, tennis courts, mini golf, and much more within steps of the Hangar House. If rain clouds ruin your tee time, use the golf simulator instead!

Guest favourite

Cabin in Cumberland

4.96 out of 5 average rating, 100 reviews

Cozy Wooded Lakeside Cabin

Rustic cabin on a small wooded lake in Cumberland, WI. Has everything you'd want and need! Cozy with an insert gas fireplace, TV, equipped kitchen, sunny porch, lake access, fire pit and spacious deck. Summer/Fall - near a bigger recreational lake and a nice golf course, both within a mile. Winter - ice fishing, cross-country skiing with lighted trails, snowmobile area.

Guest favourite

Townhouse in Cable

4.93 out of 5 average rating, 154 reviews

Cool Condo on Beautiful Lake Owen

3-bedroom 2.5 bath sleeps eight, on Wisconsin's cleanest, most beautiful lake. 2-night minimum stay. Condo includes wood fireplace, flat-screen TV, Blu-Ray/DVD, A/C, small sauna, wraparound deck, private dock, propane grill. Complex has common dock and swim area, small beach, campfire pits, picnic tables, playground and tennis courts (also marked for pickleball).