Title: Winchester Vacation Home Rentals : Search Top Private Vacation Homes for Rent | 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) # Winchester Vacation Rentals ![](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 [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248634983495009&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248634983495009&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248634983495009&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248634983495009&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winchester Vacation Homes ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/94000000/93500000/93499900/93499855/33ce6075.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/94000000/93500000/93499900/93499855/555206e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/94000000/93500000/93499900/93499855/8afb7bf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, Netflix, streaming services](https://images.trvl-media.com/lodging/94000000/93500000/93499900/93499855/6aabe767.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stylish South City 2BR w/ Garage & Blazing Wi-fi Dutchtown 9.6/10 Exceptional (48) "Very clean and comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael M. CA $113 CA $280 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/St-Louis-Hotels-Stylish-South-City-2BR-W-Garage-Blazing-Wi-Fi.h93499855.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) ![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) ![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 (150) "Clean, very nice host, cute little building. It was a little warm in there with the window unit but other wise it was amazing " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lindsay CA $116 CA $197 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/St-Louis-Hotels-Vrbo-Property.h45555760.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/105000000/104140000/104131200/104131117/1eaf5733.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/105000000/104140000/104131200/104131117/d66b4555.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, coffee/tea maker](https://images.trvl-media.com/lodging/105000000/104140000/104131200/104131117/2d023f76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/105000000/104140000/104131200/104131117/2957aa94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Honky Tonk Hideaway St. Charles Historic District 9.2/10 Wonderful (9) "Great place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Charles T. CA $126 CA $412 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/St-Louis-Hotels-Cozy-Studio-Historic-Main-Street-405-Boones-Lick-Road.h104131117.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/109000000/108940000/108939700/108939639/50d84b83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, coffee/tea maker](https://images.trvl-media.com/lodging/109000000/108940000/108939700/108939639/acfbc761.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/109000000/108940000/108939700/108939639/b37f1f7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108940000/108939700/108939639/44dc4efc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 3-bedroom house with WiFi, AC in the heart of St. Louis Northampton 8.4/10 Very good (22) "Excellent location very clean place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) kimberly b. CA $151 CA $438 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/St-Louis-Hotels-Charming-3-Bedroom-House-With-WiFi.h108939639.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107230000/107229600/107229539/b52b7a72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107230000/107229600/107229539/454cd5d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/108000000/107230000/107229600/107229539/a2372e33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/108000000/107230000/107229600/107229539/f37d57d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Convenience 2 Bedroom House to Explore All of St Louis University City 9.8/10 Exceptional (36) "Place was clean and host was accommodating." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Timothy M. CA $165 CA $372 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/St-Louis-Hotels-Convenience-2-Bedroom-House-To-Explore-All-Of-St-Louis.h107229539.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111950000/111947400/111947369/w1079h806x0y1-d6050c6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/112000000/111950000/111947400/111947369/5c698a49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111950000/111947400/111947369/d4a73c5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/112000000/111950000/111947400/111947369/53d2f95e_edited_7253.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 2-bedroom, cozy bungalow with sunroom in fabulous St. Louis with WiFi St. Louis 8.8/10 Excellent (15) "Great location! Host is super attentive. Very quick responses!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen G. CA $166 CA $270 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/St-Louis-Hotels-Charming-2-Bedroom.h111947369.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104230000/104226400/104226326/adc96c37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/105000000/104230000/104226400/104226326/07c8f12f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, offices](https://images.trvl-media.com/lodging/105000000/104230000/104226400/104226326/b708cb7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/105000000/104230000/104226400/104226326/babc771d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Adorable small house - quiet & safe - 2 BR 1 Bath Imperial 9.4/10 Exceptional (13) "Great place for a short get away" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) andytrower U. CA $137 CA $276 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Imperial-Hotels-Adorable-Small-House-Quiet-Safe-2-BR-1-Bath.h104226326.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108550000/108541500/108541428/1de1c28a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108550000/108541500/108541428/382cd829.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/109000000/108550000/108541500/108541428/870a4cbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/109000000/108550000/108541500/108541428/b83775fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 3-bedroom house with WiFi, and fenced-in backyard in serene Byrnes Mill Byrnes Mill 10/10 Exceptional (11) "Great place to stay. Huge fenced in backyard for dogs to run around. Host was real helpful with any questions we had" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael A. CA $210 CA $417 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/House-Springs-Hotels-Charming-3-Bedroom-House-With-WiFi.h108541428.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39680000/39675100/39675058/60bc2628.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/40000000/39680000/39675100/39675058/bee81703.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/40000000/39680000/39675100/39675058/27bd3ff6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/40000000/39680000/39675100/39675058/79b0d705.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### House in Soulard near Busch Stadium, Ballpark Village and Anheuser Busch Brewery Soulard 10/10 Exceptional (96) "Great place in a quiet neighborhood. Would definitely stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John S. CA $168 CA $320 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/St-Louis-Hotels-House-In-Soulard-Near-Busch-Stadium.h39675058.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120320000/120316000/120315911/be89bc35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120320000/120316000/120315911/23079201.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, offices](https://images.trvl-media.com/lodging/121000000/120320000/120316000/120315911/w1437h956x3y0-b4b1a431.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120320000/120316000/120315911/73e687bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stylish 2BR/2BA House in The Grove w/ Free Parking The Grove 10/10 Exceptional (1) "We really enjoyed our time in the Grove. This renovated property was clean and comfortable and the host was very happy to answer any questions. Highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Suzanne L. CA $123 CA $297 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/St-Louis-Hotels-Stylish-2BR2BA-House-In-The-Grove-W-Free-Parking.h120315911.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103990000/103987700/103987661/aabdcc26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/104000000/103990000/103987700/103987661/a6d8b5ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103990000/103987700/103987661/d7915e16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books, offices](https://images.trvl-media.com/lodging/104000000/103990000/103987700/103987661/2ae6fb9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic 4‑BR Farmhouse • Steps to Main Street St. Charles Historic District 10/10 Exceptional (16) "Absolutely loved the home and it truly is right in the middle of everything.. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vivian A. CA $136 CA $672 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/St-Louis-Hotels-Chic-Farmhouse-At-Historic-Frenchtown-4BR-House.h103987661.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/93000000/92210000/92203300/92203228/d9440fbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/93000000/92210000/92203300/92203228/e096975a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92210000/92203300/92203228/0dc8176f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, WiFi](https://images.trvl-media.com/lodging/93000000/92210000/92203300/92203228/305b5e79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 5th Street #1 · Historic 5th Street House - Fully Rehabbed # 1 St. Charles Historic District 9.0/10 Wonderful (10) "The house was everything we needed and the host was very responsive. Great location near historic Main Street." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sue W. CA $119 CA $325 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/St-Louis-Hotels-5th-Street-1-Historic-5th-Street-House-Fully-Rehabbed-1.h92203228.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/102000000/101190000/101188500/101188473/1e6c1c48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/102000000/101190000/101188500/101188473/4cc5d276.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101190000/101188500/101188473/59805252.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101190000/101188500/101188473/5a3d8e4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cute town house with fenced backyard Barnhart 9.6/10 Exceptional (17) "It was a great place to stay for our needs we had our little dog with us as was there for weekend, it had a nice fenced back yard we could let her just go out didn't have to have her on leash. Was very nice inside clean well kept, beds were surprising comfortable. The host stayed in contact and answered a lot questions before we arrived which put me a ease for our trip. High recommand this place if needing to stay in the area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Terry CA $169 CA $399 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Barnhart-Hotels-Cute-Town-House-3-Queen-Beds.h101188473.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/101000000/100820000/100819700/100819682/74105de3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/101000000/100820000/100819700/100819682/0c1b338f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/101000000/100820000/100819700/100819682/418d3c9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100820000/100819700/100819682/3c074e66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Below Deck Suite Saint Charles 9.0/10 Wonderful (2) "Overall good place for a family. The neighborhood is quiet and there is a good amount of space. Easy to find and to get places. You will hear the people upstairs and one bed was very squeaky. It was very clean and the couches are very comfy. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy B. CA $168 CA $364 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/St-Louis-Hotels-The-Below-Deck-Suite.h100819682.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/39000000/38730000/38727900/38727815/bf1396fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38730000/38727900/38727815/ead4bfe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/39000000/38730000/38727900/38727815/0ed5508e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/39000000/38730000/38727900/38727815/fb0dcfca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Centrally located in the Tower Grove East neighborhood! Tower Grove East 9.8/10 Exceptional (131) "Lovely place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anne S. CA $112 CA $244 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/St-Louis-Hotels-Centrally-Located-In-The-Tower-Grove-East-Neighborhood.h38727815.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/112000000/111550000/111544700/111544626/17bf0bce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/112000000/111550000/111544700/111544626/f0add46a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/112000000/111550000/111544700/111544626/5d26b9aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/112000000/111550000/111544700/111544626/cd4b7c9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Madison House 2 -Walk to Main St St. Charles Historic District 8.8/10 Excellent (5) "This property was clean and offered basic amenities, but is a very old historic home and lacks the luster and comfort of most homes, but has needed repairs and improvements to have a 5 star rating. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimbelry D. CA $119 CA $325 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/St-Louis-Hotels-Madison-House-2-Walk-To-Main-St.h111544626.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92150000/92143500/92143472/2ddbe3c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92150000/92143500/92143472/d1c8eed7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, stereo, computer monitors](https://images.trvl-media.com/lodging/93000000/92150000/92143500/92143472/1557d5d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/93000000/92150000/92143500/92143472/9fe4576c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Entire 4BR Home near Lafayette Square The Gate 9.8/10 Exceptional (82) "Nice spacious house close to lots of the places we planned to visit. It was well stocked vs most other places we have stayed meaning we did not have to go out and buy tp or paper towels or detergent. Also had an air fryer. Would stay here again if in STL. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) chris w. CA $195 CA $395 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/St-Louis-Hotels-Entire-3BR-Home-Near-Lafayette-Square.h92143472.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/112000000/111720000/111715700/111715679/e7f27cba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/112000000/111720000/111715700/111715679/442037dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/112000000/111720000/111715700/111715679/e8e12f9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/112000000/111720000/111715700/111715679/3fa24bb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quaint and Cozy Hamlet O'Fallon 9.6/10 Exceptional (8) "Kevin was super quick to reply and the place was perfect for 8 people. The place was super clean and homey! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bridget H. CA $141 CA $488 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/St-Louis-Hotels-Quaint-And-Cozy-Hamlet.h111715679.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103570000/103560400/103560390/6ac10315.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/104000000/103570000/103560400/103560390/0f6d6dda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/104000000/103570000/103560400/103560390/7e0882f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/104000000/103570000/103560400/103560390/c1313702.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cute ranch house -quiet & safe -3 BR 1 Bath Imperial 9.8/10 Exceptional (21) "Check in was interesting but owner communicated very well. Overall, it was what we needed for our trip. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patrick W. CA $154 CA $313 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Imperial-Hotels-Cute-Ranch-House-Quiet-Safe-3-BR-1-Bath.h103560390.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/83000000/82760000/82756500/82756479/dfd36c33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/83000000/82760000/82756500/82756479/267d66bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/83000000/82760000/82756500/82756479/016cf9b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/83000000/82760000/82756500/82756479/21635ab3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa de Saint Charles Saint Charles 9.2/10 Wonderful (17) "The home was perfect for our multi-family gathering. There was lots of room for everyone and the location was great for our needs." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karla Z. CA $186 CA $439 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/St-Louis-Hotels-Casa-De-Saint-Charles.h82756479.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=2025-11-11&endDate=2025-11-12®ionId=553248634983495009&adults=2&lodging=VACATION_HOME&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-Private-Vacation-Homes.d553248634983495009-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Private-Vacation-Homes.d553248634983495009-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ## Find out more about Winchester ## Winchester Vacation Homes information | Number of reviews | | | --- | --- | | Accommodation | Vacation Homes | | Lowest Price | | | Highest Price | | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - 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