Title: Winchester Guest Houses from CA $220 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d183815.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d183815.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d183815.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d183815.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) # Search Guest Houses in Winchester from CA $220 - ![](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 [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=183815&startDate=2025-12-12&endDate=2025-12-14&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=183815&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=183815&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=183815&startDate=2026-01-30&endDate=2026-02-01&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winchester Guest Houses ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90770000/90764700/90764643/3d0b43d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/91000000/90770000/90764700/90764643/8959758c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/91000000/90770000/90764700/90764643/256bf190.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90770000/90764700/90764643/00f828b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Meadowview Guest House -Couple's Hot Tub Getaway-1 Bedroom Studio Hillsboro 10/10 Exceptional (18) "I was out there for a wedding and this place was great for a weekend trip." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) L CA $115 CA $220 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Hillsboro-Hotels-Cozy-Meadowview-Guest-House-1-Bedroom-Studio-5-Minutes-To-Downtown-Hillsboro.h90764643.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=2025-12-16&endDate=2025-12-17®ionId=183815&adults=2&lodging=GUEST_HOUSE&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_183815) ![](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.d183815-aaGuestHouses.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Guest-Houses.d183815-aaGuestHouses.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Beverly hills inn](https://images.trvl-media.com/lodging/109000000/108730000/108721700/108721615/2ca35418_y.jpg) ### Beverly hills inn 10/10 Excellent "Perfect place " [](https://expedia.ca/Aberdeen-Hotels-Beverly-Hills-Inn.h108721615.Hotel-Information) ![Paragon Inn Hillsboro](https://images.trvl-media.com/lodging/3000000/2980000/2974700/2974636/8a89f8e6_y.jpg) ### Paragon Inn Hillsboro 10/10 Excellent "Room was exactly as pictured. Clean, no odors, and very pleased! Thank you so much!" [](https://expedia.ca/Hillsboro-Hotels-Paragon-Inn-Hillsboro.h2974636.Hotel-Information) ![Super 8 by Wyndham Maysville KY](https://images.trvl-media.com/lodging/1000000/50000/49900/49881/e877f7ea_y.jpg) ### Super 8 by Wyndham Maysville KY 10/10 Excellent "Staff was nice " [](https://expedia.ca/Maysville-Hotels-Super-8-By-Wyndham-Maysville-KY.h49881.Hotel-Information) ![Brown's Motel Aberdeen](https://images.trvl-media.com/lodging/11000000/10260000/10253500/10253418/4ca9fc0f_y.jpg) ### Brown's Motel Aberdeen 10/10 Excellent "Room was clean. I had a good stay! " [](https://expedia.ca/Hillsboro-Hotels-Browns-Motel-Aberdeen.h10253418.Hotel-Information) ![Days Inn by Wyndham Maysville Kentucky](https://images.trvl-media.com/lodging/1000000/30000/25500/25466/032fdf94_y.jpg) ### Days Inn by Wyndham Maysville Kentucky 10/10 Excellent "Yes the room where very clean and the staff was great " [](https://expedia.ca/Maysville-Hotels-Days-Inn-By-Wyndham-Maysville-Kentucky.h25466.Hotel-Information) ![Quality Inn Maysville](https://images.trvl-media.com/lodging/1000000/20000/17100/17042/5a32ce9b_y.jpg) ### Quality Inn Maysville 10/10 Excellent "Ty" [](https://expedia.ca/Maysville-Hotels-Quality-Inn-Maysville-Area.h17042.Hotel-Information) ![Country Nights Inn](https://images.trvl-media.com/lodging/107000000/106620000/106617100/106617030/e186aa05_y.jpg) ### Country Nights Inn 10/10 Excellent "For the price, one of the best stays I have had in a long time." [](https://expedia.ca/West-Union-Hotels-Country-Nights-Inn.h106617030.Hotel-Information) ![Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond](https://images.trvl-media.com/lodging/84000000/83540000/83536200/83536183/9bd0ec79_y.jpg) ### Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond 10/10 Excellent "Whole experience is wonderful. " [](https://expedia.ca/Peebles-Hotels-Peaceful-8-Bedroom-5-Bath-Wpatio-Bar-Grill-And-Swimming-Pond.h83536183.Hotel-Information) ![Days Inn by Wyndham Hillsboro](https://images.trvl-media.com/lodging/1000000/50000/42800/42776/0ea60812_y.jpg) ### Days Inn by Wyndham Hillsboro 10/10 Excellent "Room very clean and comfortable " [](https://expedia.ca/Hillsboro-Hotels-Days-Inn-By-Wyndham-Hillsboro.h42776.Hotel-Information) ## Find out more about Winchester ## Winchester Guest Houses information | Number of reviews | 17 | | --- | --- | | Accommodation | 1 Guest Houses | | Lowest Price | CA $220 | | Highest Price | CA $220 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [5 Star Hotels in Peebles](https://www.expedia.ca/5Star-Peebles-Hotels.s50-0-d6195740.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Sardinia](https://www.expedia.ca/5Star-Sardinia-Hotels.s50-0-d553248634983507551.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Aberdeen](https://www.expedia.ca/Aberdeen-Hotels-Cheap-Hotels.0-0-d6344064-tCheapHotels.Travel-Guide-Filter-Hotels) - 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