Title: Winchester Guest Houses from CA $116 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d3000429004.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d3000429004.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.ca/Cheap-Flights-To-Winchester.d3000429004.Travel-Guide-Flights)[Things to do in Winchester](https://expedia.ca/Things-To-Do-In-Winchester.d3000429004.Travel-Guide-Activities)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d3000429004.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d3000429004.Destination-Travel-Guides) ![Love taking pictures at grandmas house ](https://images.trvl-media.com/place/3000429004/a35ba059-b0dd-4872-9130-1f7968c86d14.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Betsy Wood # Search Guest Houses in Winchester from CA $116 - ![](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 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=3000429004&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=3000429004&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=3000429004&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=3000429004&startDate=2026-02-13&endDate=2026-02-15&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester guest houses ![Living area](https://images.trvl-media.com/lodging/90000000/89530000/89524600/89524566/62335691.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/90000000/89530000/89524600/89524566/9f64e3fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89530000/89524600/89524566/e592487f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/90000000/89530000/89524600/89524566/145736f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Balloons and Wine [](https://www.expedia.ca/Murrieta-Hotels-Balloons-And-Wine.h89524566.Hotel-Information) Murrieta 8.6/10 Excellent (17) "Great stay! Clean quiet and friendly! Everything you could ask for! Would definitely stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark CA $144 CA $162 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Murrieta-Hotels-Balloons-And-Wine.h89524566.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/89000000/88910000/88904300/88904213/9256c55d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/89000000/88910000/88904300/88904213/88279094.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Casino](https://images.trvl-media.com/lodging/89000000/88910000/88904300/88904213/4d669412.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/89000000/88910000/88904300/88904213/27342c1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private bedroom in Western Horizon Home [](https://www.expedia.ca/Hemet-Hotels-Cozy-House-Near-Wine-Country.h88904213.Hotel-Information) Hemet 9.4/10 Exceptional (29) "Place was amazing " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew CA $61 CA $125 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Hemet-Hotels-Cozy-House-Near-Wine-Country.h88904213.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/89000000/88760000/88751600/88751536/df1cbad8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shared kitchen](https://images.trvl-media.com/lodging/89000000/88760000/88751600/88751536/91fb7bfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Casino](https://images.trvl-media.com/lodging/89000000/88760000/88751600/88751536/c5beb6eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/89000000/88760000/88751600/88751536/15ecf3cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private bedroom in Peach Blossom Country House [](https://www.expedia.ca/Hemet-Hotels-Country-House-Near-Wineries.h88751536.Hotel-Information) Hemet 9.0/10 Wonderful (37) "Love staying here " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $55 CA $116 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Hemet-Hotels-Country-House-Near-Wineries.h88751536.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/34000000/33920000/33911200/33911139/3d6704a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/34000000/33920000/33911200/33911139/e5ce8cf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33920000/33911200/33911139/2db3f4f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/34000000/33920000/33911200/33911139/0e840673.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### COZY PRIVATE STUDIO GUEST HOUSE. [](https://www.expedia.ca/Temecula-Hotels-Cozy-Private-Studio-Guest-House.h33911139.Hotel-Information) Sun City 10/10 Exceptional (61) "Private and central, hosts were very nice. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julia CA $81 CA $171 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Temecula-Hotels-Cozy-Private-Studio-Guest-House.h33911139.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/42000000/41970000/41963300/41963225/w3024h4021x0y0-1a384cf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/42000000/41970000/41963300/41963225/270-0a884261.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/42000000/41970000/41963300/41963225/180-39096668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/42000000/41970000/41963300/41963225/90-1112b459.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Del Enzo Your Wine Country Hideaway CLOSE TO ALL WINERIES! [](https://www.expedia.ca/Temecula-Hotels-Villa-Del-Enzo-Your-Wine-Country-Hideaway-CLOSE-TO-ALL-WINERIES.h41963225.Hotel-Information) Temecula 9.8/10 Exceptional (220) "great view" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Doreen O. CA $173 CA $306 total includes taxes & fees Jan 3 - Jan 4, 2026 [](https://www.expedia.ca/Temecula-Hotels-Villa-Del-Enzo-Your-Wine-Country-Hideaway-CLOSE-TO-ALL-WINERIES.h41963225.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=2025-12-31&endDate=2026-01-01®ionId=3000429004&adults=2&lodging=GUEST_HOUSE&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-Guest-Houses.d3000429004-aaGuestHouses.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Guest-Houses.d3000429004-aaGuestHouses.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Tahquitz Pines Retreat](https://images.trvl-media.com/lodging/101000000/100150000/100140100/100140075/ad7ea05d_y.jpg) ### Tahquitz Pines Retreat 10/10 Excellent "Super quiet. The whole experience was superb! Will definitely be coming again! " [](https://expedia.ca/Idyllwild-Hotels-Tahquitz-Pines-Retreat.h100140075.Hotel-Information) ![Pala Casino Spa And Resort](https://images.trvl-media.com/lodging/2000000/1080000/1072000/1071947/4db651de_y.jpg) ### Pala Casino Spa And Resort 10/10 Excellent "Rooms were clean and spacious. The hotel staff were all very nice. We had a wonderful stay! " [](https://expedia.ca/Temecula-Hotels-Pala-Casino-Spa-And-Resort.h1071947.Hotel-Information) ![MainStay Suites Moreno Valley Near March Air Reserve Base](https://images.trvl-media.com/lodging/77000000/76170000/76165800/76165757/e78a9662_y.jpg) ### MainStay Suites Moreno Valley Near March Air Reserve Base 10/10 Excellent "Very cute, modern place with everything you need for a short or longer stay. The property is well maintained, and the lobby and hallways smelled clean and fresh despite some reviews saying otherwise. The bed was comfortable. It’s a bit noisy due to the highway location, but for $75 a night, I really can’t complain. I felt comfortable during my stay and would definitely stay here again. Thanks for a great stay! " [](https://expedia.ca/Riverside-Hotels-Homestay-Suites-Studios-Spas.h76165757.Hotel-Information) ![Signature Temecula](https://images.trvl-media.com/lodging/1000000/10000/3900/3867/b684d953_y.jpg) ### Signature Temecula 10/10 Excellent "12/14/25 The family and I were in town for a soccer tournament. Property and rooms were clean, check-in was easy, staff were courteous. I didn't run into any of the issues I had read about in other reviews. I would definitely stay at Signature Temecula again." [](https://expedia.ca/Temecula-Hotels-Signature-Temecula.h3867.Hotel-Information) ![Carter Estate Winery and Resort](https://images.trvl-media.com/lodging/10000000/9680000/9679100/9679100/16c52a57_y.jpg) ### Carter Estate Winery and Resort 10/10 Excellent "Instructions were needed to work the fireplace, but otherwise gave nice ambiance. " [](https://expedia.ca/Temecula-Hotels-Carter-Estate-Winery-And-Resort.h9679100.Hotel-Information) ![Home2 Suites by Hilton Temecula](https://images.trvl-media.com/lodging/33000000/32750000/32749300/32749220/25f3a2bc_y.jpg) ### Home2 Suites by Hilton Temecula 10/10 Excellent "Had a great and pleasant stay! " [](https://expedia.ca/Temecula-Hotels-Home2-Suites-By-Hilton-Temecula.h32749220.Hotel-Information) ![Motel 6 Temecula, CA - Historic Old Town](https://images.trvl-media.com/lodging/1000000/1000000/990300/990238/4e763e6b_y.jpg) ### Motel 6 Temecula, CA - Historic Old Town 10/10 Excellent "Great place!!! " [](https://expedia.ca/Temecula-Hotels-Motel-6-Temecula.h990238.Hotel-Information) ![Murrieta Hot Springs Resort](https://images.trvl-media.com/lodging/102000000/101390000/101380300/101380271/2b0b7a85_y.jpg) ### Murrieta Hot Springs Resort 10/10 Excellent "Amazing getaway! Beautiful spot for a little soak, massage and rejuvenation. Highly recommend 👍" [](https://expedia.ca/Murrieta-Hotels-Murrieta-Hot-Springs-Resort.h101380271.Hotel-Information) ![Europa Village Wineries and Resort](https://images.trvl-media.com/lodging/23000000/22120000/22113700/22113617/19749642_y.jpg) ### Europa Village Wineries and Resort 10/10 Excellent "Good service" [](https://expedia.ca/Temecula-Hotels-The-Inn-At-Europa-Village.h22113617.Hotel-Information) ## Find out more about Winchester ## Winchester Guest Houses information | Number of reviews | 364 | | ----------------- | --------------- | | Accommodation | 29 Guest Houses | | Lowest Price | CA $116 | | Highest Price | CA $306 | ## Frequently asked questions ### What are the most popular guest houses in Winchester according to reviews? ### What is the nightly rate for a guest house in Winchester? ### What's the difference between a Winchester guest house and a B&B? ## Explore a world of travel with Expedia - Lodging - Flights - Cars - Vacation Rental - More ways to book - [Hotels near Diamond Valley Lake Marina ](https://www.expedia.ca/Diamond-Valley-Lake-Marina-Hotels.0-l6197611-0.Travel-Guide-Filter-Hotels) - 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