Title: Winchester Guest Houses from CA $197 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d553248634983495009.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d553248634983495009.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d553248634983495009.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d553248634983495009.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.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 Next weekend [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=553248634983495009&startDate=2026-02-27&endDate=2026-03-01&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=553248634983495009&startDate=2026-03-06&endDate=2026-03-08&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=553248634983495009&startDate=2026-03-20&endDate=2026-03-22&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=553248634983495009&startDate=2026-04-17&endDate=2026-04-19&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester guest houses ![Smart TV](https://images.trvl-media.com/lodging/40000000/40000000/39999800/39999703/7fbfaa77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/40000000/40000000/39999800/39999703/f8988c01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/40000000/40000000/39999800/39999703/594765b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/40000000/40000000/39999800/39999703/99bcfaee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy, Fun, and One-Of-A-Kind! [](https://www.expedia.ca/St-Louis-Hotels-Cozy.h39999703.Hotel-Information) Shaw 9.4/10 Exceptional (121 reviews) "Cute place - exactly what we needed for this trip to St. Louis. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angela L. CA $79 CA $197 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/St-Louis-Hotels-Cozy.h39999703.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/46000000/45770000/45765200/45765177/03e2f810.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive Room, 1 King Bed, Connecting Rooms](https://images.trvl-media.com/lodging/46000000/45770000/45765200/45765177/0dc01800.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/46000000/45770000/45765200/45765177/fd41b80b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/46000000/45770000/45765200/45765177/2d13aedc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Grand Center Inn [](https://www.expedia.ca/St-Louis-Hotels-GRAND-CENTER-INN.h45765177.Hotel-Information) Grand Center 9.4/10 Exceptional (75 reviews) "Clean room. Excellent host Eric! Historic home Eric very attentive and helpful with all tips about St. Louis!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pamela CA $210 CA $248 total includes taxes & fees Mar 2 - Mar 3 [](https://www.expedia.ca/St-Louis-Hotels-GRAND-CENTER-INN.h45765177.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=2026-03-04&endDate=2026-03-05®ionId=553248634983495009&adults=2&lodging=GUEST_HOUSE&sort=RECOMMENDED&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_553248634983495009) ![](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%2FWinchester-Guest-Houses.d553248634983495009-aaGuestHouses.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Guest-Houses.d553248634983495009-aaGuestHouses.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Pear Tree Inn St. Louis Airport](https://images.trvl-media.com/lodging/2000000/1100000/1096600/1096579/fc156cf2_y.jpg) ### Pear Tree Inn St. Louis Airport 10/10 Excellent "We felt very welcome when we arrived and were invited to some popcorn and soda as an evening snack. Our room was spotless and comfortable. The breakfast was delicious, hot, and a terrific way to begin our day of travel." [](https://expedia.ca/St-Louis-Hotels-Pear-Tree-Inn-St-Louis-Airport.h1096579.Hotel-Information) ![Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham](https://images.trvl-media.com/lodging/1000000/50000/42200/42122/bfca870c_y.jpg) ### Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham 10/10 Excellent "Everything was good" [](https://expedia.ca/St-Louis-Hotels-Drury-Inn-Suites-St-Louis-Fenton.h42122.Hotel-Information) ![The Wildwood Hotel](https://images.trvl-media.com/lodging/2000000/1770000/1768200/1768149/800a6847_y.jpg) ### The Wildwood Hotel 10/10 Excellent "Extremely nice hotel with the nicest staff!!" [](https://expedia.ca/St-Louis-Hotels-The-Wildwood-Hotel.h1768149.Hotel-Information) ![Pear Tree Inn St. Louis Near Union Station](https://images.trvl-media.com/lodging/1000000/30000/26600/26572/0bb9dbf3_y.jpg) ### Pear Tree Inn St. Louis Near Union Station 10/10 Excellent "The room was very clean. Amenities were great. The staff was great!! They all went far beyond the norm. Would definitely stay there again." [](https://expedia.ca/St-Louis-Hotels-Pear-Tree-Inn-St-Louis-Near-Union-Station.h26572.Hotel-Information) ![Hilton St. Louis Airport](https://images.trvl-media.com/lodging/1000000/10000/7800/7743/w2900h1927x0y0-a7e2c287_y.jpg) ### Hilton St. Louis Airport 10/10 Excellent "Clean and very close to airport. " [](https://expedia.ca/St-Louis-Hotels-Hilton-St-Louis-Airport.h7743.Hotel-Information) ![Hampton Inn St. Louis-Downtown (At the Gateway Arch)](https://images.trvl-media.com/lodging/1000000/30000/22600/22520/w3837h2560x0y0-a6354f1b_y.jpg) ### Hampton Inn St. Louis-Downtown (At the Gateway Arch) 10/10 Excellent "Paula at the front desk was amazing! " [](https://expedia.ca/St-Louis-Hotels-Hampton-Inn-Gateway-Arch-Downtown.h22520.Hotel-Information) ![Clayton Plaza Hotel & Extended Stay](https://images.trvl-media.com/lodging/1000000/20000/18200/18144/b3c5d3cd_y.jpg) ### Clayton Plaza Hotel & Extended Stay 10/10 Excellent "Considering the price I wasn’t expecting such a nice place, from the entrance, to the easy parking, to the amazing breakfast… everything was so great and I would 1000% consider this place for my future stays in St. Louis! The staff was also very helpful and friendly!" [](https://expedia.ca/St-Louis-Hotels-Clayton-Plaza-Hotel-Extended-Stay.h18144.Hotel-Information) ![Angad Arts Hotel St. Louis, Tapestry Collection by Hilton](https://images.trvl-media.com/lodging/28000000/27620000/27617000/27616925/25bc97a8_y.jpg) ### Angad Arts Hotel St. Louis, Tapestry Collection by Hilton 10/10 Excellent "Very clean, even friendlier." [](https://expedia.ca/St-Louis-Hotels-Angad-Arts-Hotel-St-Louis.h27616925.Hotel-Information) ![River City Casino & Hotel](https://images.trvl-media.com/lodging/7000000/6460000/6456500/6456459/33f9207d_y.jpg) ### River City Casino & Hotel 10/10 Excellent "Clean, quiet, comfortable; friendly staff" [](https://expedia.ca/St-Louis-Hotels-River-City-Casino-Hotel.h6456459.Hotel-Information) ## Find out more about Winchester ## Winchester Guest Houses information | Number of reviews | 195 | | ----------------- | -------------- | | Accommodation | 4 Guest Houses | | Lowest Price | CA $197 | | Highest Price | CA $248 | ## 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) - 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