Title: Book the Best Winterset WINERY Hotels in 2025 | Expedia.ca [Hotels in Winterset](https://expedia.ca/Winterset-Hotels.d181516.Travel-Guide-Hotels)[Vacation Rentals in Winterset](https://expedia.ca/Winterset-Vacation-Rentals.d181516.Travel-Guide-VacationRentals)[Flights to Winterset](https://expedia.ca/Cheap-Flights-To-Winterset.d181516.Travel-Guide-Flights)[Winterset Car Rentals](https://expedia.ca/Car-Rentals-In-Winterset.d181516.Car-Rental-Guide)[Winterset Vacation Packages](https://expedia.ca/Winterset.d181516.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/830fc6762ccc71fc6b71a5e80242e57e.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Tonette Pineda✈⛵🚌🚉🚃🚅🚀 # Find Winery Hotels in Winterset, IA from CA $120 ![](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 availability on Winterset Winery Hotels Tonight [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=181516&startDate=2025-10-14&endDate=2025-10-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=181516&startDate=2025-10-15&endDate=2025-10-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=181516&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=181516&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winterset Winery Hotels ![Desk, laptop workspace, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/1000000/70000/64300/64224/f2b63f8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/70000/64300/64224/39dd45ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/70000/64300/64224/b0883037.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/70000/64300/64224/755041e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Osceola Osceola 8.6/10 Excellent (56) "Worth the stay" CA $126 CA $141 total includes taxes & fees Oct 18 - Oct 19 [](https://www.expedia.ca/Osceola-Hotels-Quality-Inn-Osceola.h64224.Hotel-Information) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/910000/906800/906757/3fc13a33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/910000/906800/906757/a9738a38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/910000/906800/906757/02743800.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/910000/906800/906757/2482ce8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Indianola Indianola 7.6/10 Good (506) "Very happy with the hospitality, very polite and accommodating. Great location and easy to find." CA $107 CA $120 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Des-Moines-Hotels-Quality-Inn-Indianola.h906757.Hotel-Information) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/23000000/22690000/22689900/22689811/04073782.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/23000000/22690000/22689900/22689811/860d68c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, desk, blackout drapes](https://images.trvl-media.com/lodging/23000000/22690000/22689900/22689811/b397336b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/23000000/22690000/22689900/22689811/2c8a57f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Pommier Indianola Indianola 9.2/10 Wonderful (419) "Very nice facility. Convenient location when visiting central Iowa. " CA $122 CA $136 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Des-Moines-Hotels-Hotel-Pommier.h22689811.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109910000/109908000/109907977/eba8e617.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109910000/109908000/109907977/2cc94ff9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109910000/109908000/109907977/518166ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/110000000/109910000/109908000/109907977/aa836835.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Hen House Country Living with Farm Life Appeal Indianola, IA Indianola 10/10 Exceptional (7) "Our host was amazing. Went above to make sure we had a great stay. Very personable..We both enjoyed visiting with her and learning more about the area. We will definitely return to the Hen House" CA $189 CA $265 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Indianola-Hotels-The-Hen-House-Country-Living-With-Farm-Life-Appeal.h109907977.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33490000/33489500/33489445/e2e34c89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33490000/33489500/33489445/010fed97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33490000/33489500/33489445/361b2528.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/34000000/33490000/33489500/33489445/90-0e2233fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Rustic Barn just waiting for you to kick back and relax. NEW VIRGINIA 10/10 Exceptional (402) "Needed a a quick getaway....it was perfect " CA $145 CA $250 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Beautiful-Rustic-Barn-Just-Waiting-For-You-To-Kick-Back-And-Relax.h33489445.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90930000/90929000/90928974/ef19ea0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90930000/90929000/90928974/eca2a319.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/91000000/90930000/90929000/90928974/66d5f361.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/91000000/90930000/90929000/90928974/8660a89c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly Remodeled Brick Home with wall Sculptures by the Airport Southwestern Hills 9.8/10 Exceptional (41) "Great place in a nice quiet neighborhood. " CA $195 CA $297 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Des-Moines-Hotels-Newly-Remodeled-Brick-Home-With-Wall-Sculptures-By-The-Airport.h90928974.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/109000000/109000000/108998200/108998176/bf9f7f27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/109000000/109000000/108998200/108998176/d50a6d28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/109000000/109000000/108998200/108998176/12a1a3c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/109000000/109000000/108998200/108998176/3a6875d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Love Shack | Spacious Family Getaway • 5BR/3BA • 10 Mins to Downtown Windsor Heights 10/10 Exceptional (10) "Great house for our family to stay and gather between weddings events! Easy to get to and had lots of space to hang out. " CA $225 CA $612 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Des-Moines-Hotels-The-Love-Shack-Spacious-Family-Getaway.h108998176.Hotel-Information) ![Smart TV, offices, computer monitors, printers](https://images.trvl-media.com/lodging/93000000/92410000/92407400/92407393/0de18b7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/93000000/92410000/92407400/92407393/23daad62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92410000/92407400/92407393/7ad08de9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92410000/92407400/92407393/d9bd72e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### No Stairs! Garage Included! Ton's of Extras! West Des Moines 9.8/10 Exceptional (16) "Property was clean and quite. This made my stay comfortable and enjoyable.The complex was convenient to family and shopping. I'm looking forward to staying here again." CA $118 CA $335 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/West-Des-Moines-Hotels-Private-Garage-Huge-Gym-First-Floor-Wifi.h92407393.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78050000/78040100/78040035/1181db94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/79000000/78050000/78040100/78040035/08b92c48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78050000/78040100/78040035/5c85e6ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, table tennis](https://images.trvl-media.com/lodging/79000000/78050000/78040100/78040035/ac92223c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOL. WE HAVE IT ALL! Urbandale 9.4/10 Exceptional (71) "We had a fun time staying at this house. We visited downtown Des Moines and had a great time at Adventureland. The only suggestion would be to have some dish towels in the kitchen. The arcade games, ping pong table and skee-ball were popular with the kids. " CA $289 CA $728 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Des-Moines-Hotels-The-Aurora-Fun-For-Everyone-Games-Galore-Perfect-For-Group-Entertaining.h78040035.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/52000000/51880000/51876700/51876665/w1621h912x9y0-a31d7f5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/52000000/51880000/51876700/51876665/d2200545.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor banquet area](https://images.trvl-media.com/lodging/52000000/51880000/51876700/51876665/dd98e326.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/52000000/51880000/51876700/51876665/df6ae836.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ultimate Luxurious Party House New Virginia CA $1,263 CA $1,515 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Luxury-Estate-Vineyards.h51876665.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. 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