Title: Winchester Guest Houses from CA $260 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d7876.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d7876.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d7876.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d7876.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/2d4532767bd47b707b21acca86317ffc.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Hyelsinta # Search Guest Houses in Winchester from CA $260 ![](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 [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winchester Guest Houses ![Outdoor dining](https://images.trvl-media.com/lodging/38000000/37620000/37611200/37611132/20aa5388.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/38000000/37620000/37611200/37611132/352dd92f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/38000000/37620000/37611200/37611132/a6c86c19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/38000000/37620000/37611200/37611132/380cc537.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury on Main / North Richmond 9.8/10 Exceptional (103) "Great stay, will be back again!" CA $137 CA $260 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Lexington-Hotels-Luxury-On-Main-North.h37611132.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=2025-10-25&endDate=2025-10-26®ionId=7876&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.d7876-aaGuestHouses.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Guest-Houses.d7876-aaGuestHouses.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Motel 6 Lexington, KY - East I-75](//images.trvl-media.com/lodging/2000000/1040000/1039800/1039703/c1f9e9cf_y.jpg) ### Motel 6 Lexington, KY - East I-75 10/10 Excellent "Thanks for your service " [](https://expedia.ca/Lexington-Hotels-Motel-6-Lexington.h1039703.Hotel-Information) ![Holiday Inn Lexington - Hamburg by IHG](//images.trvl-media.com/lodging/23000000/22760000/22757700/22757695/776ae294_y.jpg) ### Holiday Inn Lexington - Hamburg by IHG 10/10 Excellent "All fine and friendly" [](https://expedia.ca/Lexington-Hotels-Holiday-Inn-Lexington-Hamburg.h22757695.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Lexington South / Hamburg](//images.trvl-media.com/lodging/1000000/290000/283200/283165/60f6cd78_y.jpg) ### La Quinta Inn & Suites by Wyndham Lexington South / Hamburg 10/10 Excellent "Clean room. Friendly staff. Good breakfast." [](https://expedia.ca/Lexington-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Lexington-South-Hamburg.h283165.Hotel-Information) ![The Manchester ](//images.trvl-media.com/lodging/93000000/92440000/92430600/92430541/f02815a4_y.jpg) ### The Manchester 10/10 Excellent "Great property! " [](https://expedia.ca/Lexington-Hotels-The-Manchester.h92430541.Hotel-Information) ![Spark by Hilton Lexington Hamburg](//images.trvl-media.com/lodging/1000000/10000/6700/6639/4dbc3493_y.jpg) ### Spark by Hilton Lexington Hamburg 10/10 Excellent "Clean room and friendly staff " [](https://expedia.ca/Lexington-Hotels-Spark-By-Hilton-Lexington-Hamburg.h6639.Hotel-Information) ![GuestHouse Lexington](//images.trvl-media.com/lodging/1000000/430000/426400/426325/18dc9903_y.jpg) ### GuestHouse Lexington 10/10 Excellent "Clean room! Everything great! TV practically knew! Wi-Fi superb! A great bargain! Excellent, hot breakfast! I love the location!" [](https://expedia.ca/Lexington-Hotels-GuestHouse-Lexington.h426325.Hotel-Information) ![Hyatt Regency Lexington](//images.trvl-media.com/lodging/1000000/10000/3500/3461/c0c49295_y.jpg) ### Hyatt Regency Lexington 10/10 Excellent "Perfect location for Rupp Arena venue. Check in was quick and overall hotel was nice and clean. " [](https://expedia.ca/Lexington-Hotels-Hyatt-Regency-Lexington.h3461.Hotel-Information) ![Origin Lexington a Wyndham Hotel](//images.trvl-media.com/lodging/34000000/33800000/33790700/33790682/7bb47690_y.jpg) ### Origin Lexington a Wyndham Hotel 10/10 Excellent "Thank you for a pleasant stay. Great lication. Everyone was very welcoming, professional and friendly. I will definitely recommend the Origin to all our friends traveling to Lexington." [](https://expedia.ca/Lexington-Hotels-Origin-Hotel-Lexington.h33790682.Hotel-Information) ![Embassy Suites by Hilton Lexington/UK Coldstream](//images.trvl-media.com/lodging/1000000/210000/203600/203587/32ffb492_y.jpg) ### Embassy Suites by Hilton Lexington/UK Coldstream 10/10 Excellent "Nice queen, big rooms, complementary drinks and a very good breakfast. Well, Worth the stay" [](https://expedia.ca/Lexington-Hotels-Embassy-Suites-By-Hilton-LexingtonUK-Coldstream.h203587.Hotel-Information) ## Find out more about Winchester ## Winchester Guest Houses information | Number of reviews | 103 | | --- | --- | | Accommodation | 3 Guest Houses | | Lowest Price | CA $260 | | Highest Price | CA $260 | ## Frequently asked questions ### What are the most popular guest houses in Winchester according to reviews? > [College Park Bungalow](https://www.expedia.ca/Lexington-Hotels-College-Park-Bungalow.h113819513.Hotel-Information) is a great choice for travellers seeking a cozy retreat in Winchester, offering a warm and friendly space. With convenient onsite parking and a well-equipped kitchen, it provides the superb setting for those who value quality and convenience. Guests have praised the bungalow for its thoughtful amenities, making it an ideal home base for exploring the charming surroundings of Winchester. ### What is the nightly rate for a guest house in Winchester? > Rates for Winchester guest houses vary, but travelers can find great-value prices from CA $260 with Expedia. A range of factors can affect nightly rates, such as the location, the breakfast offering, and the range of amenities. Travelers looking for a good deal should consider looking for a midweek stay, as weekend rates at Winchester guest houses tend to be higher. Remember to also use our filters to sort prices from low to high. ### What's the difference between a Winchester guest house and a B&B? > A guest house in Winchester is typically a larger establishment with more rooms, offering a more hotel-like experience, and may provide additional amenities including luxury bedding. In contrast, a B&B is usually a smaller property that focuses primarily on providing a room and breakfast. A B&B is often more personal, and breakfast is typically included as part of the stay, but other services might be more limited compared to a guest house. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [Hotels near Applebee s Park](https://www.expedia.ca/Applebee-S-Park-Hotels.0-l553248621557921127-0.Travel-Guide-Filter-Hotels) - [Motels in Camargo](https://www.expedia.ca/Camargo-Motels.d553248634998850038-aaMotels.Travel-Guide-Accommodation) - [Beach Hotel Hotels in Chevy Chase](https://www.expedia.ca/Chevy-Chase-Lexington-Hotels-Beach-Hotel.0-n553248635976481361-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Golf Hotels in Chevy Chase](https://www.expedia.ca/Chevy-Chase-Lexington-Hotels-Golf-Hotel.0-n553248635976481361-0-tGolfHotel.Travel-Guide-Filter-Hotels) - [Hotels with smoking rooms in Chevy Chase](https://www.expedia.ca/Chevy-Chase-Lexington-Hotels-Hotels-With-Smoking-Rooms.0-n553248635976481361-0-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels) - 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