Title: Winchester Guest Houses from CA $280 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d553248635975876131.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d553248635975876131.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d553248635975876131.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d553248635975876131.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 $280 - ![](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 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635975876131&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635975876131&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=553248635975876131&startDate=2026-01-09&endDate=2026-01-11&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248635975876131&startDate=2026-02-06&endDate=2026-02-08&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester guest houses ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/46000000/45690000/45688300/45688247/cf77662c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/46000000/45690000/45688300/45688247/2658c1d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/46000000/45690000/45688300/45688247/26cb2420.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/46000000/45690000/45688300/45688247/01e73ddf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Short Street Studio [](https://www.expedia.ca/Smithville-Hotels-Short-Street-Studio.h45688247.Hotel-Information) Downtown Smithville 9.2/10 Wonderful (11) "Really enjoyed staying at this lovely studio apartment. Very clean, peaceful, and had everything we needed for our stay. Close to downtown Smithville and in a very cute neighborhood. Would stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathryn F. CA $138 CA $280 total includes taxes & fees Dec 11 - Dec 12 [](https://www.expedia.ca/Smithville-Hotels-Short-Street-Studio.h45688247.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/45000000/44360000/44357400/44357397/b004d1bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/45000000/44360000/44357400/44357397/01077ed8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/45000000/44360000/44357400/44357397/f3f6685d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/45000000/44360000/44357400/44357397/1b576edb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Farmstead Round Top [](https://www.expedia.ca/Brenham-Hotels-Farmstead-Round-Top.h44357397.Hotel-Information) Round Top 9.8/10 Exceptional (47) "Amazing place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jesus [](https://www.expedia.ca/Brenham-Hotels-Farmstead-Round-Top.h44357397.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=2025-12-24&endDate=2025-12-25®ionId=553248635975876131&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.d553248635975876131-aaGuestHouses.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Guest-Houses.d553248635975876131-aaGuestHouses.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Days Inn by Wyndham Bastrop](https://images.trvl-media.com/lodging/1000000/60000/50700/50700/ad509697_y.jpg) ### Days Inn by Wyndham Bastrop 10/10 Excellent "Usual basic amenities, excellent staff." [](https://expedia.ca/Bastrop-Hotels-Days-Inn-By-Wyndham-Bastrop.h50700.Hotel-Information) ![Best Western La Grange Inn & Suites](https://images.trvl-media.com/lodging/2000000/1530000/1522900/1522868/f3514b92_y.jpg) ### Best Western La Grange Inn & Suites 10/10 Excellent "Friendly staff and great service " [](https://expedia.ca/Columbus-Hotels-Best-Western-La-Grange-Inn-Suites.h1522868.Hotel-Information) ![Best Western Giddings Inn & Suites](https://images.trvl-media.com/lodging/4000000/3980000/3972200/3972119/460c006b_y.jpg) ### Best Western Giddings Inn & Suites 10/10 Excellent "Yes" [](https://expedia.ca/Brenham-Hotels-Best-Western-Giddings-Inn-Suites.h3972119.Hotel-Information) ![River Valley Motor Inn](https://images.trvl-media.com/lodging/1000000/980000/973500/973410/7699e214_y.jpg) ### River Valley Motor Inn 10/10 Excellent "Nice" [](https://expedia.ca/Columbus-Hotels-River-Valley-Motor-Inn.h973410.Hotel-Information) ![Hampton Inn La Grange](https://images.trvl-media.com/lodging/5000000/4040000/4034200/4034198/d00d75f8_y.jpg) ### Hampton Inn La Grange 10/10 Excellent "Nice clean rooms and very quiet. Staff was friendly and breakfast ok. However the outside of the hotel could use a little TLC. Weeds growing, cigarette butts, and not much maintenance!" [](https://expedia.ca/Columbus-Hotels-Hampton-Inn-La-Grange.h4034198.Hotel-Information) ![Super 8 by Wyndham Giddings](https://images.trvl-media.com/lodging/1000000/50000/43100/43006/788e0c4e_y.jpg) ### Super 8 by Wyndham Giddings 10/10 Excellent "The rooms were clean beds were great . Only thing better if the air-conditioner would have been on before arrival. " [](https://expedia.ca/Brenham-Hotels-Super-8-By-Wyndham-Giddings.h43006.Hotel-Information) ![Studio 6 – Giddings, Tx](https://images.trvl-media.com/lodging/120000000/119080000/119074600/119074593/91f9af0e_y.jpg) ### Studio 6 – Giddings, Tx 10/10 Excellent "Conveniently location " [](https://expedia.ca/Giddings-Hotels-Studio-6-Giddings.h119074593.Hotel-Information) ![The Oak Motel](https://images.trvl-media.com/lodging/20000000/19300000/19293900/19293884/dc1affde_y.jpg) ### The Oak Motel 10/10 Excellent "Great staff clean rooms close to shopping and dining " [](https://expedia.ca/Columbus-Hotels-The-Oak-Motel.h19293884.Hotel-Information) ![Adorable Guest Cabin In The Woods](https://images.trvl-media.com/lodging/94000000/93230000/93225600/93225597/e1c70a94_y.jpg) ### Adorable Guest Cabin In The Woods 10/10 Excellent "Charming getaway surrounded by beautiful pines and quiet, natural grounds that you can explore. Host communications are excellent. Bed is very comfy. " [](https://expedia.ca/La-Grange-Hotels-Adorable-Guest-Cabin-In-The-Woods.h93225597.Hotel-Information) ## Find out more about Winchester ## Winchester Guest Houses information | Number of reviews | 57 | | ----------------- | -------------- | | Accommodation | 6 Guest Houses | | Lowest Price | CA $280 | | Highest Price | CA $280 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [5 Star Hotels in Paige ](https://www.expedia.ca/5Star-Paige-Hotels.s50-0-d6352494.Travel-Guide-Filter-Hotels) - [Farmstay in Bastrop County ](https://www.expedia.ca/Bastrop-County-Agritourism.d553248635976433953-aaAgritourism.Travel-Guide-Accommodation) - [Guest Houses in Bastrop ](https://www.expedia.ca/Bastrop-Guest-Houses.d55572-aaGuestHouses.Travel-Guide-Accommodation) - [Cheap Hotels in Bastrop ](https://www.expedia.ca/Bastrop-Hotels-Cheap-Hotels.0-0-d55572-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Bastrop ](https://www.expedia.ca/Bastrop-Hotels-Couples-Resorts-Hotels.0-0-d55572-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - 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