Title: Book the Best Chesterfield WINERY Hotels in 2025 | 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)[Things to do in Chesterfield](https://expedia.ca/Things-To-Do-In-Chesterfield.d9530.Travel-Guide-Activities)[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) ![](https://mediaim.expedia.com/destination/2/59a833585731f0877f894eab85319bc4.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Michelle E # Find Winery Hotels in Chesterfield, MO from CA $153 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [Oct 6 - Oct 7](https://www.expedia.ca/Hotel-Search?regionId=9530&startDate=2025-10-06&endDate=2025-10-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 7 - Oct 8](https://www.expedia.ca/Hotel-Search?regionId=9530&startDate=2025-10-07&endDate=2025-10-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=9530&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=9530&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chesterfield Winery Hotels ![1 bedroom, Egyptian cotton sheets, premium bedding, pillowtop beds](https://images.trvl-media.com/lodging/2000000/1080000/1077200/1077183/23b516cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Laundry room](https://images.trvl-media.com/lodging/2000000/1080000/1077200/1077183/64d8ca2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1080000/1077200/1077183/f94e668c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1080000/1077200/1077183/3a1e3bea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Washington Hotel Washington 9.0/10 Wonderful (604) " Great value. Very friendly staff and comfortable rooms." CA $180 CA $205 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Washington-Hotels-Best-Western-Plus-Washington-Hotel.h1077183.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) ![Bar (on property)](https://images.trvl-media.com/lodging/74000000/73340000/73337200/73337142/a0c10e84.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) ![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) ### The Inn at Elijah McLeans Washington 9.0/10 Wonderful (129) "Modern" CA $171 CA $195 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Washington-Hotels-The-Inn-At-Elijah-McLeans.h73337142.Hotel-Information) ![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) ![Egyptian cotton sheets, premium bedding, pillowtop beds, desk](https://images.trvl-media.com/lodging/1000000/50000/42200/42154/cb77ee79.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) ### Hampton Inn St. Louis/Chesterfield Chesterfield 8.6/10 Excellent (1004) "Great staff and atmosphere " CA $142 CA $165 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/St-Louis-Hotels-Hampton-Inn-St-LouisChesterfield.h42154.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99340000/99335800/99335731/93da6846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/100000000/99340000/99335800/99335731/e0c9496d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/100000000/99340000/99335800/99335731/c3984d33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99340000/99335800/99335731/39f35d15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wine Country Getaway | JZ Vacation Rentals Washington 8.0/10 Very good (1) "Great communication, had a couple of leaks and shower flooded but the maintenance came right away to fix it. Overall clean, AC/Heat unit in each room, big kitchen, wonderful sitting area and decor." CA $232 CA $579 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Washington-Hotels-Stylish-Home-Near-Wine-Country-JZ-Vacation-Rentals.h99335731.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/46000000/45560000/45555800/45555760/w903h683x61y0-189c70ff.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 (149) "Very walkable to everything in The Hill area! " CA $104 CA $185 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/St-Louis-Hotels-Vrbo-Property.h45555760.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89710000/89709500/89709402/80473f5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/90000000/89710000/89709500/89709402/906263b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/90000000/89710000/89709500/89709402/w1025h690x0y88-55244220.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89710000/89709500/89709402/85986c02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tiny Cozy Cottage in a Big City Park Free Benton Park West 10/10 Exceptional (44) "We loved the location and accommodations. Perfect for our weekend trip." CA $98 CA $181 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/St-Louis-Hotels-Tiny-Cottage-On-Historic-Antique-Row.h89709402.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) ![Shower, towels](https://images.trvl-media.com/lodging/111000000/110070000/110062700/110062608/c7db1510.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) ### Adorable Augusta Cabin Augusta 9.0/10 Wonderful (8) "Absolutely beautiful area. Cabin is so cozy" CA $128 CA $296 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Augusta-Hotels-Adorable-Augusta-Cabin.h110062608.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) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/60000/50700/50618/ecdf92ac.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) ### Best Western Plus St. Louis Airport Hotel Woodson Terrace 9.2/10 Wonderful (1005) "It was great stay, nice people!" CA $141 CA $175 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/St-Louis-Hotels-Best-Western-Plus-St-Louis-Airport-Hotel.h50618.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/107000000/106720000/106715700/106715696/1822a31a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The West End Central West End 8.4/10 Very good (331) "hotel rooms were very clean. it was a nice quiet hotel. loved my stay" CA $108 CA $153 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/St-Louis-Hotels-The-West-End.h106715696.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107230000/107221400/107221352/c06a9779.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107230000/107221400/107221352/da797f5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107230000/107221400/107221352/45f3f0d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107230000/107221400/107221352/30179f6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The West End Hotel- 2 Queen Beds Central West End 6.0/10 (2) "The property is nice. It's clean and the people were very friendly. The beds were quite comfortable, though the pillows are very fluffy, if you like them more flat then you might bring your own, but I was very happy with the room and accommodations. The garage is worth the price to park and there's a cute patio area with plenty of seating and a separate hot tub area, all conveniently located by the rear exit. A big plus for us is that it was close to the venue we were going to for our stay and... CA $139 CA $412 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/St-Louis-Hotels-The-West-End-2-Queen-Beds.h107221352.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=2025-10-20&endDate=2025-10-21®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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