Title: Winner Vacation Home Rentals from CA $195: Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in Winner](https://expedia.ca/Winner-Hotels.d175746.Travel-Guide-Hotels)[Vacation Rentals in Winner](https://expedia.ca/Winner-Vacation-Rentals.d175746.Travel-Guide-VacationRentals)[Flights to Winner](https://expedia.ca/Cheap-Flights-To-Winner.d175746.Travel-Guide-Flights)[Winner Car Rentals](https://expedia.ca/Car-Rentals-In-Winner.d175746.Car-Rental-Guide)[Winner Vacation Packages](https://expedia.ca/Winner.d175746.Destination-Travel-Guides) ![Aerial View of Winner, South Dakota in Winter](https://images.trvl-media.com/place/175746/88f45c4b-56bf-41e0-ab6e-f73f4f08d246.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/175746/88f45c4b-56bf-41e0-ab6e-f73f4f08d246.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 In two weeks [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=175746&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=175746&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=175746&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 26 - Jun 28](https://www.expedia.ca/Hotel-Search?regionId=175746&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winner vacation homes ![Exterior detail](https://images.trvl-media.com/lodging/91000000/90850000/90842300/90842218/793c06c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/91000000/90850000/90842300/90842218/132ca649.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90850000/90842300/90842218/fb21281c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90850000/90842300/90842218/e8641202.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Winner [](https://www.expedia.ca/Winner-Hotels-Cozy-Little-Getaway.h90842218.Hotel-Information) 10/10 Exceptional (12 reviews) "Great place to stay, nice and cool in there! Very clean! Would stay again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jen CA $123 CA $195 total includes taxes & fees Mar 4 - Mar 5 [](https://www.expedia.ca/Winner-Hotels-Cozy-Little-Getaway.h90842218.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/69000000/68280000/68275600/68275528/80676e6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/69000000/68280000/68275600/68275528/1dc7cda1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![7 bedrooms, bed sheets](https://images.trvl-media.com/lodging/69000000/68280000/68275600/68275528/0bdc667c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/69000000/68280000/68275600/68275528/1b45e795.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Dallas [](https://www.expedia.ca/The-Ranch-You-Love.h68275528.Hotel-Information) 9.4/10 Exceptional (19 reviews) "This property was great for our large group. Everyone had their own space and we enjoyed coming together in the common areas for fun." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jerry D. CA $341 CA $625 total includes taxes & fees Mar 4 - Mar 5 [](https://www.expedia.ca/The-Ranch-You-Love.h68275528.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/117000000/116800000/116790900/116790894/a3642be8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116800000/116790900/116790894/886389ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116790900/116790894/64f462c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, stereo](https://images.trvl-media.com/lodging/117000000/116800000/116790900/116790894/ef299327.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Gregory [](https://www.expedia.ca/Gregory-Hotels-Rustic-Ridge.h116790894.Hotel-Information) 9.6/10 Exceptional (5 reviews) "Every thing was great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mike T. CA $252 CA $465 total includes taxes & fees Mar 4 - Mar 5 [](https://www.expedia.ca/Gregory-Hotels-Rustic-Ridge.h116790894.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=2026-03-17&endDate=2026-03-18®ionId=175746&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AA_SPRING_PROMO_175746) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.ca/Hotel-Search?destination=Winner%2C+South+Dakota%2C+United+States+of+America®ionId=175746&latLong=43.254485%2C-99.925868&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=CABIN) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Winner%2C+South+Dakota%2C+United+States+of+America®ionId=175746&latLong=43.254485%2C-99.925868&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=VACATION_HOME) ![](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%2FWinner-Private-Vacation-Homes.d175746-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinner-Private-Vacation-Homes.d175746-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Winner Hotel Reviews ![Raine Motel](https://images.trvl-media.com/lodging/49000000/48970000/48962900/48962869/366d0842_y.jpg) ### Raine Motel 10/10 Excellent "yes, it is clean enough & the services was awesome" [](https://expedia.ca/Valentine-Hotels-Raine-Motel.h48962869.Hotel-Information) ![Trade Winds Motel](https://images.trvl-media.com/lodging/2000000/1660000/1659000/1658963/b25751e5_y.jpg) ### Trade Winds Motel 10/10 Excellent "Friendly staff good location Little far out of town but okay easy to get back in town plenty of parking clean rooms comfortable beds ok breakfast" [](https://expedia.ca/Valentine-Hotels-Trade-Winds-Motel.h1658963.Hotel-Information) ![Holiday Inn Express & Suites Winner by IHG](https://images.trvl-media.com/lodging/1000000/910000/903300/903274/85a55cce_y.jpg) ### Holiday Inn Express & Suites Winner by IHG 10/10 Excellent "Everything was great!!!" [](https://expedia.ca/Winner-Hotels-Holiday-Inn-Express-Suites-Winner.h903274.Hotel-Information) ![Comfort Inn Valentine](https://images.trvl-media.com/lodging/1000000/10000/5700/5657/c1fc2815_y.jpg) ### Comfort Inn Valentine 10/10 Excellent "Very clean and nice people checking in and out " [](https://expedia.ca/Valentine-Hotels-Comfort-Inn-Valentine.h5657.Hotel-Information) ![Harmony Inn & Suites](https://images.trvl-media.com/lodging/4000000/3550000/3542300/3542265/875388b0_y.jpg) ### Harmony Inn & Suites 10/10 Excellent "Room spotless" [](https://expedia.ca/Valentine-Hotels-Harmony-Inn-Suites.h3542265.Hotel-Information) ![Super 8 by Wyndham Valentine NE](https://images.trvl-media.com/lodging/1000000/900000/897900/897836/1393a55b_y.jpg) ### Super 8 by Wyndham Valentine NE 10/10 Excellent "Great staff. Nice hot tub. Nice room. " [](https://expedia.ca/Valentine-Hotels-Super-8-By-Wyndham-Valentine-NE.h897836.Hotel-Information) ![Sandhills retreat minutes from downtown Valentine](https://images.trvl-media.com/lodging/123000000/122070000/122068800/122068769/w1079h749x0y1-32602b16_y.jpg) ### Sandhills retreat minutes from downtown Valentine 10/10 Excellent "This property was welcoming and sitting in an amazing part of Valentine. The host is amazing and very helpful. We highly recommend this property. " [](https://expedia.ca/Valentine-Hotels-Sandhills-Retreat-Minutes-From-Downtown-Valentine.h122068769.Hotel-Information) ![King's Inn](https://images.trvl-media.com/lodging/20000000/19440000/19435000/19434979/0506c717_y.jpg) ### King's Inn 10/10 Excellent "The owners were no nice ! " [](https://expedia.ca/Chamberlain-Hotels-Kings-Inn.h19434979.Hotel-Information) ![Super 8 by Wyndham Winner SD](https://images.trvl-media.com/lodging/2000000/1330000/1329500/1329421/f9a92518_y.jpg) ### Super 8 by Wyndham Winner SD 10/10 Excellent "Staff was very nice, hotel was very clean! " [](https://expedia.ca/Winner-Hotels-Super-8-By-Wyndham-Winner-SD.h1329421.Hotel-Information) ## Find out more about Winner ## Winner Vacation Homes information | Number of reviews | 36 | | ----------------- | ---------------- | | Accommodation | 5 Vacation Homes | | Lowest Price | CA $195 | | Highest Price | CA $625 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [3 Star Hotels in Chamberlain ](https://www.expedia.ca/3Star-Chamberlain-Hotels.s30-0-d6059499.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Dixon ](https://www.expedia.ca/5Star-Dixon-Hotels.s50-0-d6352575.Travel-Guide-Filter-Hotels) - [Antelope Hotels ](https://www.expedia.ca/Antelope-Hotels.d553248634983527139.Travel-Guide-Hotels) - [Farmstay in Burke ](https://www.expedia.ca/Burke-Agritourism.d553248634983107572-aaAgritourism.Travel-Guide-Accommodation) - [Cottages in Burke ](https://www.expedia.ca/Burke-Cottages.d553248634983107572-aaCottages.Travel-Guide-Accommodation) - 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