Title: Winter Condo Rentals from CA $284 | Expedia.ca [Winter Travel Guide](https://expedia.ca/Winter.dx3000462138)[Hotels in Winter](https://expedia.ca/Winter-Hotels.d3000462138.Travel-Guide-Hotels)[Vacation Rentals in Winter](https://expedia.ca/Winter-Vacation-Rentals.d3000462138.Travel-Guide-VacationRentals)[Flights to Winter](https://expedia.ca/Cheap-Flights-To-Winter.d3000462138.Travel-Guide-Flights)[Winter Car Rentals](https://expedia.ca/Car-Rentals-In-Winter.d3000462138.Car-Rental-Guide)[Winter Vacation Packages](https://expedia.ca/Winter.d3000462138.Destination-Travel-Guides) ![Big Bay State Park on Madeline Island. Spring 2016 Series, Madeline Island, Wisconsin (May 2016); Shutterstock ID 446953213; Purchase Order: -](https://images.trvl-media.com/place/6094008/acc71183-9f8c-4587-9754-eafcd171fbf7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Condos Rentals in Winter from CA $284 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=3000462138&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=3000462138&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=3000462138&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=3000462138&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winter condo rentals ![Deluxe Suite, 1 Bedroom, Kitchen | Terrace/patio](https://images.trvl-media.com/lodging/36000000/35270000/35263100/35263087/6f590308.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/36000000/35270000/35263100/35263087/e3700c21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/36000000/35270000/35263100/35263087/87ac838f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Condo | Private kitchen](https://images.trvl-media.com/lodging/36000000/35270000/35263100/35263087/a47bd9ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Cable [](https://www.expedia.ca/Hayward-Hotels-Telemark-Vacation-Condominiums.h35263087.Hotel-Information) 9.0/10 Wonderful (316) "Colors of the trees were beautiful, staff helpful, trails plentiful and walkable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kenneth CA $204 CA $430 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Hayward-Hotels-Telemark-Vacation-Condominiums.h35263087.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89830000/89829400/89829386/w1916h1436x4y4-1d9223cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89830000/89829400/89829386/59abc923.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/90000000/89830000/89829400/89829386/w1920h1437x0y3-9d1617d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/90000000/89830000/89829400/89829386/ad07a39b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Phillips [](https://www.expedia.ca/Phillips-Hotels-Red-Pines-Elk-Lake-Condo-1-3-Bedroom.h89829386.Hotel-Information) 10/10 Exceptional (13) "Fantastic Place !!!!!! It was great and exactly what we needed!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ryan CA $222 CA $284 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Phillips-Hotels-Red-Pines-Elk-Lake-Condo-1-3-Bedroom.h89829386.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/90000000/89830000/89829400/89829395/bf32f5e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi](https://images.trvl-media.com/lodging/90000000/89830000/89829400/89829395/47c2d37e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89830000/89829400/89829395/1d22890c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89830000/89829400/89829395/6868a23a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Phillips [](https://www.expedia.ca/Phillips-Hotels-Red-Pines-Elk-Lake-Condo-4-2-Bed.h89829395.Hotel-Information) 10/10 Exceptional (1) "We had a very short stay but it was great from check-in to check-out. Great communication, extremely clean and very cozy. A true Northwoods experience!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rachel K. CA $222 CA $287 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Phillips-Hotels-Red-Pines-Elk-Lake-Condo-4-2-Bed.h89829395.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/90000000/89830000/89829400/89829389/d4e385e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89830000/89829400/89829389/8aff646f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/90000000/89830000/89829400/89829389/baab997c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/90000000/89830000/89829400/89829389/w1920h1203x0y3-47d4afbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Phillips [](https://www.expedia.ca/Phillips-Hotels-Red-Pines-Elk-Lake-Condo-3-2-Bed.h89829389.Hotel-Information) 9.8/10 Exceptional (8) "Great place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cody CA $222 CA $287 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Phillips-Hotels-Red-Pines-Elk-Lake-Condo-3-2-Bed.h89829389.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/90000000/89830000/89829400/89829393/9178c57a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89830000/89829400/89829393/w1920h1437x0y3-ff26e19e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/90000000/89830000/89829400/89829393/w1917h1436x3y4-977e23c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89830000/89829400/89829393/b1904e6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Phillips [](https://www.expedia.ca/Phillips-Hotels-Red-Pines-Elk-Lake-Condo-6-3-Bed.h89829393.Hotel-Information) 10/10 Exceptional (4) "Clean, comfortable, well furnished and roomy. Walkout access to the lake. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew B. CA $222 CA $287 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Phillips-Hotels-Red-Pines-Elk-Lake-Condo-6-3-Bed.h89829393.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89830000/89829400/89829391/c9224fd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89830000/89829400/89829391/b5d600a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89830000/89829400/89829391/999143c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/90000000/89830000/89829400/89829391/a3dd0ca5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Phillips [](https://www.expedia.ca/Phillips-Hotels-Red-Pines-Elk-Lake-Condo-2-2-Bed.h89829391.Hotel-Information) 10/10 Exceptional (2) "This place was perfect for my stay. It was very clean, in a great location, and the property manager was very helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew G. CA $222 CA $287 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Phillips-Hotels-Red-Pines-Elk-Lake-Condo-2-2-Bed.h89829391.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-04&endDate=2026-01-05®ionId=3000462138&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.ca/Hotel-Search?destination=Winter%2C+Wisconsin%2C+United+States+of+America®ionId=3000462138&latLong=45.819683%2C-91.011833&adults=2&startDate=2026-03-21&d1=2026-03-21&endDate=2026-03-24&d2=2026-03-24&lodging=CABIN) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Winter%2C+Wisconsin%2C+United+States+of+America®ionId=3000462138&latLong=45.819683%2C-91.011833&adults=2&startDate=2026-03-21&d1=2026-03-21&endDate=2026-03-24&d2=2026-03-24&lodging=VACATION_HOME) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Winter%2C+Wisconsin%2C+United+States+of+America®ionId=3000462138&latLong=45.819683%2C-91.011833&adults=2&startDate=2026-03-21&d1=2026-03-21&endDate=2026-03-24&d2=2026-03-24&lodging=COTTAGE) Condos [](https://www.expedia.ca/Hotel-Search?destination=Winter%2C+Wisconsin%2C+United+States+of+America®ionId=3000462138&latLong=45.819683%2C-91.011833&adults=2&startDate=2026-03-21&d1=2026-03-21&endDate=2026-03-24&d2=2026-03-24&lodging=CONDO) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Winter%2C+Wisconsin%2C+United+States+of+America®ionId=3000462138&latLong=45.819683%2C-91.011833&adults=2&startDate=2026-03-21&d1=2026-03-21&endDate=2026-03-24&d2=2026-03-24&lodging=APARTMENT) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinter-Condos.d3000462138-aaCondos.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinter-Condos.d3000462138-aaCondos.Travel-Guide-Accommodation) ## Top Winter Hotel Reviews ![Cozy Cabin on Secluded Peninsula](https://images.trvl-media.com/lodging/86000000/85480000/85471500/85471498/451f9cb4_y.jpg) ### Cozy Cabin on Secluded Peninsula 10/10 Excellent "Took a 2 day trip to celebrate an anniversary. Could have picked a better weekend as far as being able to enjoy outdoor activities. Temps never reached positive numbers during our stay. Even with that the cabin was very comfortable and cozy. " [](https://expedia.ca/Hayward-Hotels-Osprey-Cabin.h85471498.Hotel-Information) ![Hayward Lakefront - Gorgeous Cabin, Four Seasons of Fun for up to 21 guests](https://images.trvl-media.com/lodging/35000000/34090000/34084700/34084617/a431dbd7_y.jpg) ### Hayward Lakefront - Gorgeous Cabin, Four Seasons of Fun for up to 21 guests 10/10 Excellent "Very attentive host - checked in with us to make sure everything was going well. The space was gorgeous, comfortable and spacious for our group. Yoga in the loft!" [](https://expedia.ca/Hayward-Hotels-Hayward-Lakefront-Gorgeous-Cabin.h34084617.Hotel-Information) ![Holiday Inn Express & Suites Hayward by IHG](https://images.trvl-media.com/lodging/1000000/290000/280900/280853/2970951b_y.jpg) ### Holiday Inn Express & Suites Hayward by IHG 10/10 Excellent "Amazing stay with pretty lake views, and wonderful with two young kids. Big, open common spaces with activities/games for adults and kids. Pool was great, hot tub jets were not working but it was hot and circulating, sauna was hot and spacious but the benches could use fixing. Room was recently renovated, two queen beds and a pull out couch - microwave and mini fridge too. Overall a great property for our two nights. " [](https://expedia.ca/Hayward-Hotels-Holiday-Inn-Express-Suites-Hayward.h280853.Hotel-Information) ![Executive Custom Log Lodge on Little Round Lake](https://images.trvl-media.com/lodging/54000000/53820000/53814700/53814694/w1206h682x6y0-e4cd60e6_y.jpg) ### Executive Custom Log Lodge on Little Round Lake 10/10 Excellent "The house was an excellent place for our family Thanksgiving get together. VERY spacious and comfortable. It was clean and well equipped. We enjoyed our stay. " [](https://expedia.ca/Hayward-Hotels-Executive-Custom-Log-Lodge-On-Little-Round-Lake.h53814694.Hotel-Information) ![Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!](https://images.trvl-media.com/lodging/21000000/20150000/20143800/20143722/ea1fb32a_y.jpg) ### Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails! 10/10 Excellent "Perfect location and amenities with lakefront privacy. This stay had all of the things needed for a relaxing, comfortable and enjoyable stay. Landings for Lake Chippewa, downtown and great dining options were all within a 20 minute drive. Ample firewood was provided, quick communication from the owner and all in all a perfect getaway. Highly recommend this property! " [](https://expedia.ca/Hayward-Hotels-Very-Private-Cabin-On-Upper-Twin-Lakelarge-Lotgreat-Views.h20143722.Hotel-Information) ![Modern Cabin located between Grindstone and Lac Courte Oreilles](https://images.trvl-media.com/lodging/74000000/73980000/73977700/73977614/05a04408_y.jpg) ### Modern Cabin located between Grindstone and Lac Courte Oreilles 10/10 Excellent "Very cozy cabin. Already stocked with everything you need. Hosts had great suggestions for local supper clubs!" [](https://expedia.ca/Hayward-Hotels-Modern-Cabin-Located-Between-Grindstone-And-Lac-Courte-Oreilles.h73977614.Hotel-Information) ![AmericInn by Wyndham Ladysmith](https://images.trvl-media.com/lodging/1000000/850000/848400/848383/3c822ae4_y.jpg) ### AmericInn by Wyndham Ladysmith 10/10 Excellent "Great stay. Clean room and comfy bed for a tired traveler!! " [](https://expedia.ca/Rice-Lake-Hotels-Ladysmith-Motel-Suites.h848383.Hotel-Information) ![5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.](https://images.trvl-media.com/lodging/54000000/53820000/53817500/53817438/w4026h3024x2y0-727608df_y.jpg) ### 5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis. 10/10 Excellent "We rent someplace in the Winter area every year in October for a weeklong grouse hunt. This cabin was by far our favorite. It was exceptionally cleaned, well kept, well stocked, and well laid out. Chris was a fantastic and accommodating host and made sure everything was set for our arrival. I would highly recommend this property for any group. It is a great combination of multiple comfortable living spaces in a peaceful quiet setting." [](https://expedia.ca/Winter-Hotels-Beautiful-3-Bedroom-Lake-Home-Near-Winter.h53817438.Hotel-Information) ![Hayward, Round Lake Retreat! Private dock, 3 kayaks, beautifully maintained! ](https://images.trvl-media.com/lodging/72000000/71550000/71545200/71545160/9d0d39b2_y.jpg) ### Hayward, Round Lake Retreat! Private dock, 3 kayaks, beautifully maintained! 10/10 Excellent "Third time renting here, property is comfortable, clean and well equipped. The only teeny, tiny “I hate to mention” issue was the wine bottle opener was difficult to use. Otherwise, all was wonderful!" [](https://expedia.ca/Hayward-Hotels-Round-Lake-Timberlane-Lodge.h71545160.Hotel-Information) ## Find out more about Winter ## Winter Condo Rentals information | Number of reviews | 342 | | ----------------- | ---------------- | | Accommodation | 16 Condo Rentals | | Lowest Price | CA $284 | | Highest Price | CA $430 | ## Frequently asked questions ### Why book your condo in Winter with Expedia? ### How can I find cheap condos in Winter? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [4 Star Hotels in Hayward ](https://www.expedia.ca/4Star-Hayward-Hotels.s40-0-d7773.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Northwoods Beach ](https://www.expedia.ca/4Star-Northwoods-Beach-Hayward-Hotels.s40-n553248635975849216-0.Travel-Guide-Filter-Hotels) - [Hotels near American Birkebeiner Trail ](https://www.expedia.ca/American-Birkebeiner-Trail-Hotels.0-l553248621561861926-0.Travel-Guide-Filter-Hotels) - [Hotels near Chequamegon National Forest ](https://www.expedia.ca/Chequamegon-National-Forest-Hotels.0-l6094008-0.Travel-Guide-Filter-Hotels) - 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