Title: Winchester B&B: Find the Best Bed and Breakfast from CA $219 | 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 [Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=553248634983495009&startDate=2026-04-17&endDate=2026-04-19&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=553248634983495009&startDate=2026-04-24&endDate=2026-04-26&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=553248634983495009&startDate=2026-05-08&endDate=2026-05-10&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jun 5 - Jun 7](https://www.expedia.ca/Hotel-Search?regionId=553248634983495009&startDate=2026-06-05&endDate=2026-06-07&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester bed & breakfast ![Hallway](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326573/c44211f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Private Bathroom (Thomas Hart Benton Suite)](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326573/f11fe4c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326573/790c3c44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326573/f26ee42c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Benton Park Inn [](https://www.expedia.ca/St-Louis-Hotels-Benton-Park-Inn.h17326573.Hotel-Information) Benton Park 9.6/10 Exceptional (321 reviews) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Conor CA $193 CA $225 total includes taxes & fees Apr 12 - Apr 13 [](https://www.expedia.ca/St-Louis-Hotels-Benton-Park-Inn.h17326573.Hotel-Information) ![Miscellaneous](https://images.trvl-media.com/lodging/13000000/12520000/12514000/12513911/a1fd6a1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/13000000/12520000/12514000/12513911/77e6e6a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, Ensuite (Alaska)](https://images.trvl-media.com/lodging/13000000/12520000/12514000/12513911/7f33d300.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/13000000/12520000/12514000/12513911/7b17b7b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Lodge at Grant's Trail [](https://www.expedia.ca/St-Louis-Hotels-The-Lodge-At-Grants-Trail.h12513911.Hotel-Information) St. Louis 9.6/10 Exceptional (486 reviews) "This was a perfect property for us. The staff were so friendly and welcoming. We will definitely stay there again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jean CA $191 CA $219 total includes taxes & fees Apr 13 - Apr 14 [](https://www.expedia.ca/St-Louis-Hotels-The-Lodge-At-Grants-Trail.h12513911.Hotel-Information) ![Suite, Private Bathroom (Diamonds and Pearls Luxury Suite)](https://images.trvl-media.com/lodging/18000000/17680000/17678300/17678265/4d85105d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Private Bathroom (Diamonds and Pearls Luxury Suite)](https://images.trvl-media.com/lodging/18000000/17680000/17678300/17678265/3920214a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Private Bathroom](https://images.trvl-media.com/lodging/18000000/17680000/17678300/17678265/133b0297.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Private Bathroom (Reflections)](https://images.trvl-media.com/lodging/18000000/17680000/17678300/17678265/4bba56a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Central West End B&B [](https://www.expedia.ca/St-Louis-Hotels-Central-West-End-Bed-And-Breakfast.h17678265.Hotel-Information) Central West End 8.0/10 Very good (55 reviews) "My husband & I were very impressed with the hostess Ms. Henrietta Taylor she made us feel at home with her hospitality. She keeps the establishment immaculate, and served a scrumptious homemade breakfast! I highly recommend this bed & breakfast in the Central West End of St. Louis, Missouri to all family & friends! 2 Thumbs Up 👍👍!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tammy CA $222 CA $280 total includes taxes & fees Apr 12 - Apr 13 [](https://www.expedia.ca/St-Louis-Hotels-Central-West-End-Bed-And-Breakfast.h17678265.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/124000000/123230000/123226400/123226385/5ef15c5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/124000000/123230000/123226400/123226385/bd2ca7be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/124000000/123230000/123226400/123226385/68ba0ae5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/124000000/123230000/123226400/123226385/f17a5079.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### West End Hotel- Queen Bed by Cortex, Forest Park and BJC [](https://www.expedia.ca/St-Louis-Hotels-West-End-Hotel-Queen-Bed-By-Cortex.h123226385.Hotel-Information) Central West End CA $135 CA $431 total includes taxes & fees Apr 12 - Apr 13 [](https://www.expedia.ca/St-Louis-Hotels-West-End-Hotel-Queen-Bed-By-Cortex.h123226385.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=2026-04-21&endDate=2026-04-22®ionId=553248634983495009&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&openPlayBack=true) ![](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-Bed-And-Breakfast.d553248634983495009-aaBedAndBreakfast.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Bed-And-Breakfast.d553248634983495009-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![The Westin St. Louis](https://images.trvl-media.com/lodging/1000000/470000/460400/460354/665259c4_y.jpg) ### The Westin St. Louis 10/10 Excellent "This hotel was amazing! I forgot a phone charger & one of the maintenance guys ran out to his truck to get me one. The rooms were amazing. The bathroom was like a spa! Cannot wait to stay there again. " [](https://expedia.ca/St-Louis-Hotels-The-Westin-St-Louis.h460354.Hotel-Information) ![Hotel Indigo St Louis - Central West End by IHG](https://images.trvl-media.com/lodging/1000000/30000/22100/22068/bd89b9ce_y.jpg) ### Hotel Indigo St Louis - Central West End by IHG 6/10 Okay "The hotel was the nice the staff was not." [](https://expedia.ca/St-Louis-Hotels-Holiday-Inn-Express-St-Louis-Central-West-End.h22068.Hotel-Information) ![Hilton St. Louis Airport](https://images.trvl-media.com/lodging/1000000/10000/7800/7743/c57dfbd2_y.jpg) ### Hilton St. Louis Airport 10/10 Excellent "Love this hotel! Very convenient and modern!" [](https://expedia.ca/St-Louis-Hotels-Hilton-St-Louis-Airport.h7743.Hotel-Information) ![Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham](https://images.trvl-media.com/lodging/1000000/50000/42200/42122/b53f4594_y.jpg) ### Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham 10/10 Excellent "The room and hotel was clean. The staff was very helpful and friendly. Only complaint was that the pool was very cold! To be inside I wish it was a little warmer " [](https://expedia.ca/St-Louis-Hotels-Drury-Inn-Suites-St-Louis-Fenton.h42122.Hotel-Information) ![Pear Tree Inn St. Louis Near Union Station](https://images.trvl-media.com/lodging/1000000/30000/26600/26572/3056142b_y.jpg) ### Pear Tree Inn St. Louis Near Union Station 6/10 Okay "My kids appreciated the pool (crowded as it was!). The happy hour and fountain soda in the breakfast area was a pleasant surprise. Rooms are a bit worn, hallway looked like it had some water issues as well with missing tiles/exposed pipes. Bed was too soft for me. We had to switch rooms due to wet carpet by the AC; staff was very accommodating, but it was an inconvenience after we had unpacked." [](https://expedia.ca/St-Louis-Hotels-Pear-Tree-Inn-St-Louis-Near-Union-Station.h26572.Hotel-Information) ![Hollywood Casino & Hotel St. Louis](https://images.trvl-media.com/lodging/1000000/90000/82600/82568/76ca3207_y.jpg) ### Hollywood Casino & Hotel St. Louis 6/10 Okay "It is an ok place " [](https://expedia.ca/St-Louis-Hotels-Hollywood-Casino-Hotel-St-Louis.h82568.Hotel-Information) ![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 "Great stay I have no complains" [](https://expedia.ca/St-Louis-Hotels-Pear-Tree-Inn-St-Louis-Airport.h1096579.Hotel-Information) ![Hyatt Regency St. Louis at The Arch](https://images.trvl-media.com/lodging/1000000/20000/14900/14877/c1e52387_y.jpg) ### Hyatt Regency St. Louis at The Arch 10/10 Excellent "Nice stay at an older downtown hotel. Was in walking distance of most attractions we were in town for. Very quiet even though there were several middle and high school girls volleyball teams in town for a tournament. Would definitely stay there again. " [](https://expedia.ca/St-Louis-Hotels-Hyatt-Regency-St-Louis-At-The-Arch.h14877.Hotel-Information) ![Forest Park Hotel by MDR](https://images.trvl-media.com/lodging/1000000/30000/22300/22298/460db328_y.jpg) ### Forest Park Hotel by MDR 10/10 Excellent "It was great, no complaints! A great property, quiet and clean!" [](https://expedia.ca/St-Louis-Hotels-Holiday-Inn-St-Louis-Forest-Park.h22298.Hotel-Information) ## Find out more about Winchester ## Winchester B&B information | Number of reviews | 862 | | ----------------- | ------- | | Accommodation | 7 B&B | | Lowest Price | CA $219 | | Highest Price | CA $431 | ## Frequently asked questions ### Searching for B&Bs in Winchester? ### Why consider B&Bs instead of traditional hotels? ### What are the best B&Bs in Winchester? ### When is the best time to book my B&B in Winchester? ### How can I get to and around Winchester? ## 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) - 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