Title: Book the Best Chesterfield WINERY Hotels in 2026 | Expedia.ca [Chesterfield Travel Guide](https://expedia.ca/Chesterfield.dx9530)[Hotels in Chesterfield](https://expedia.ca/Chesterfield-Hotels.d9530.Travel-Guide-Hotels)[Vacation Rentals in Chesterfield](https://expedia.ca/Chesterfield-Vacation-Rentals.d9530.Travel-Guide-VacationRentals)[Flights to Chesterfield](https://expedia.ca/Cheap-Flights-To-Chesterfield.d9530.Travel-Guide-Flights)[Chesterfield Car Rentals](https://expedia.ca/Car-Rentals-In-Chesterfield.d9530.Car-Rental-Guide)[Chesterfield Vacation Packages](https://expedia.ca/Chesterfield.d9530.Destination-Travel-Guides) ![autumn landscape with lake Chesterfield Missouri](https://images.trvl-media.com/place/9530/c6d3b4d9-41bc-4a55-9787-aa13d1650621.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Chesterfield, MO from CA $146 - ![](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 Chesterfield Winery Hotels Tonight [Dec 5 - Dec 6](https://www.expedia.ca/Hotel-Search?regionId=9530&startDate=2025-12-05&endDate=2025-12-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 6 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=9530&startDate=2025-12-06&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=9530&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=9530&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chesterfield Winery Hotels ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/50000/42200/42154/54d31f1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/50000/42200/42154/399fe339.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/42200/42154/1ac706c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, pillowtop beds, desk](https://images.trvl-media.com/lodging/1000000/50000/42200/42154/1057ce09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn St. Louis/Chesterfield Chesterfield 8.6/10 Excellent (1001) "The older gentleman who checked us in was great! Breakfast was delicious, particularly the potatoes!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amber CA $126 CA $146 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/St-Louis-Hotels-Hampton-Inn-St-LouisChesterfield.h42154.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/50700/50618/dc7136af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/60000/50700/50618/c4174534.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/60000/50700/50618/1410e5e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pillowtop beds, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/60000/50700/50618/c60f07ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus St. Louis Airport Hotel Woodson Terrace 9.2/10 Wonderful (1000) "I love staying here everything is great. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Claudia Marlene CA $153 CA $189 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/St-Louis-Hotels-Best-Western-Plus-St-Louis-Airport-Hotel.h50618.Hotel-Information) ![Casino](https://images.trvl-media.com/lodging/2000000/1880000/1873300/1873292/c42cf5fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hot tub, body treatments, hydrotherapy, aromatherapy, body scrubs](https://images.trvl-media.com/lodging/2000000/1880000/1873300/1873292/422bb82f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 restaurants, breakfast served](https://images.trvl-media.com/lodging/2000000/1880000/1873300/1873292/d825c5c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1880000/1873300/1873292/502ee41b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ameristar Casino Resort and Spa St. Charles 8.4/10 Very good (1000) "Clean room, wonderful helpful pleasant staff, amenities, everything was great love staying here!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robyn CA $187 CA $242 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/St-Louis-Hotels-Ameristar-Casino-Resort-And-Spa.h1873292.Hotel-Information) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/110070000/110062700/110062608/46f64c9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110070000/110062700/110062608/5d45ed4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/111000000/110070000/110062700/110062608/0589f65d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/111000000/110070000/110062700/110062608/7d7d40ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Adorable Augusta Cabin Augusta 9.0/10 Wonderful (9) "Absolutely beautiful area. Cabin is so cozy" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Aaron CA $128 CA $299 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Augusta-Hotels-Adorable-Augusta-Cabin.h110062608.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/910000/904800/904712/4c313173.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/1000000/910000/904800/904712/11973fba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/910000/904800/904712/567cfa11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/1000000/910000/904800/904712/82e45c33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Marriott St. Louis Grand Downtown St. Louis 8.2/10 Very good (1001) "Very convenient to the local sites we wanted to visit." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Garland CA $177 CA $211 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/St-Louis-Hotels-Marriott-St-Louis-Grand.h904712.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/46000000/45560000/45555800/45555760/6072f683.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/46000000/45560000/45555800/45555760/w504h683x260y0-d473b0d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/46000000/45560000/45555800/45555760/w906h683x59y0-c5f27c19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/46000000/45560000/45555800/45555760/w468h683x271y0-af1736d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!! The Hill 9.8/10 Exceptional (159) "Very clean, check in was easy, great neighborhood with lots of food close. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura H. CA $113 CA $194 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/St-Louis-Hotels-Vrbo-Property.h45555760.Hotel-Information) ![Balcony view](https://images.trvl-media.com/lodging/74000000/73340000/73337200/73337142/c782f87e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/74000000/73340000/73337200/73337142/da468407.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Single Room](https://images.trvl-media.com/lodging/74000000/73340000/73337200/73337142/1e3360cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Single Room](https://images.trvl-media.com/lodging/74000000/73340000/73337200/73337142/c71db8b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Elijah McLeans Washington 8.8/10 Excellent (133) "Modern" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan CA $171 CA $195 total includes taxes & fees Dec 31 - Jan 1, 2026 [](https://www.expedia.ca/Washington-Hotels-The-Inn-At-Elijah-McLeans.h73337142.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106720000/106715700/106715696/ccf67b25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/107000000/106720000/106715700/106715696/1822a31a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee/tea maker, highchair](https://images.trvl-media.com/lodging/107000000/106720000/106715700/106715696/49927158.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/107000000/106720000/106715700/106715696/2c313b99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The West End Central West End 8.4/10 Very good (401) "Friendly staff, great rooms; and I love the north brew coffee place were the VIP access coffee is redeemed " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Miguel CA $129 CA $178 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/St-Louis-Hotels-The-West-End.h106715696.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/84000000/83410000/83401500/83401435/709bd7f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/84000000/83410000/83401500/83401435/bb002526.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83410000/83401500/83401435/942b0e3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/84000000/83410000/83401500/83401435/a9dde174.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Cyclist! Katy Trail comfort in Marthasville,MO Marthasville 9.8/10 Exceptional (10) "Wonderful place to get away to and relax!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Timothy J. CA $213 CA $337 total includes taxes & fees Dec 6 - Dec 7 [](https://www.expedia.ca/Marthasville-Hotels-The-Cyclist-Katy-Trail-Comfort-In-Marthasville.h83401435.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/97000000/96280000/96274600/96274548/57c584b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96280000/96274600/96274548/1e4863b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96280000/96274600/96274548/6c389783.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96280000/96274600/96274548/b63cea66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### TheOutPostInn Bed&Breakfast - The Blue Victorian Marthasville 8.6/10 Excellent (7) "Stayed in Hermann one night and here one night. Great space, comfy bed, quiet area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erin A. CA $152 CA $255 total includes taxes & fees Dec 6 - Dec 7 [](https://www.expedia.ca/Marthasville-Hotels-TheOutPostInn-BedBreakfast-The-Blue-Victorian.h96274548.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=2025-12-19&endDate=2025-12-20®ionId=9530&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Chesterfield Hotel Reviews ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [5 Star Hotels in Town and Country ](https://www.expedia.ca/5Star-Town-And-Country-Hotels.s50-0-d6252549.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Ballwin ](https://www.expedia.ca/Ballwin-Hotels-Beach-Hotel.0-0-d6354554-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Ballwin ](https://www.expedia.ca/Ballwin-Hotels-Cheap-Hotels.0-0-d6354554-tCheapHotels.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Ballwin ](https://www.expedia.ca/Ballwin-Hotels-Romantic-Hotel.0-0-d6354554-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Ballwin Hotels ](https://www.expedia.ca/Ballwin-Hotels.d6354554.Travel-Guide-Hotels) - [Vacation Homes in Ballwin ](https://www.expedia.ca/Ballwin-Private-Vacation-Homes.d6354554-aaPrivateVacationHomes.Travel-Guide-Accommodation) - 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