Title: Winchester Guest Houses from CA $284 | 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 $284 ![](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=553248635975876131&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635975876131&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635975876131&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [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) ## Browse Select 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) ![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) ![Interior](https://images.trvl-media.com/lodging/46000000/45690000/45688300/45688247/2658c1d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Short Street Studio Downtown Smithville 9.0/10 Wonderful (9) "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 $140 CA $284 total includes taxes & fees Oct 29 - Oct 30 [](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) ![Farmstead Round Top - Cottage](https://images.trvl-media.com/lodging/45000000/44360000/44357400/44357397/9cc4a941.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) ![Exterior](https://images.trvl-media.com/lodging/45000000/44360000/44357400/44357397/01077ed8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Farmstead Round Top Round Top 9.8/10 Exceptional (46) "Amazing place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jesus CA $268 CA $333 total includes taxes & fees Oct 29 - Oct 30 [](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=2025-11-11&endDate=2025-11-12®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 ![Hampton Inn La Grange](//images.trvl-media.com/lodging/5000000/4040000/4034200/4034198/d00d75f8_y.jpg) ### Hampton Inn La Grange 10/10 Excellent "I had an issues with my reservation then I need to sleep in the floor. Forn dels help me amazingly to make ma door bed. " [](https://expedia.ca/Columbus-Hotels-Hampton-Inn-La-Grange.h4034198.Hotel-Information) ![Studio 6 – Giddings, Tx](//images.trvl-media.com/lodging/120000000/119080000/119074600/119074593/75c5a08e_y.jpg) ### Studio 6 – Giddings, Tx 10/10 Excellent "Everything was great. " [](https://expedia.ca/Giddings-Hotels-Studio-6-Giddings.h119074593.Hotel-Information) ![Super 8 by Wyndham Giddings](//images.trvl-media.com/lodging/1000000/50000/43100/43006/788e0c4e_y.jpg) ### Super 8 by Wyndham Giddings 10/10 Excellent "PLeasant stay. Clean rooms. Well kept property. Good staff. " [](https://expedia.ca/Brenham-Hotels-Super-8-By-Wyndham-Giddings.h43006.Hotel-Information) ![Americas Best Value Inn Giddings](//images.trvl-media.com/lodging/2000000/1330000/1326100/1326031/58dd682d_y.jpg) ### Americas Best Value Inn Giddings 10/10 Excellent "Room was very clean and sheets were crisp and clean. Staff was very friendly Not going to lie was very skeptical about this place We stayed on the single story side And we will stay here in Giddings,Tx again." [](https://expedia.ca/Brenham-Hotels-Americas-Best-Value-Inn-Giddings.h1326031.Hotel-Information) ![Angeltom Cabin & RV:20 Acre Woods - >16 pip + Jacuzzi + treehouse + UTV + 2ponds](//images.trvl-media.com/lodging/23000000/22350000/22343800/22343739/988b0bb9_y.jpg) ### Angeltom Cabin & RV:20 Acre Woods - >16 pip + Jacuzzi + treehouse + UTV + 2ponds 10/10 Excellent "Everything was great! We can't wait to come back. " [](https://expedia.ca/Columbus-Hotels-Angeltom-Cabin-RV-10-Acre-Woods-Sleeps-Up-To-14-People.h22343739.Hotel-Information) ![Adorable Guest Cabin In The Woods](//images.trvl-media.com/lodging/94000000/93230000/93225600/93225597/e1c70a94_y.jpg) ### Adorable Guest Cabin In The Woods 10/10 Excellent "It’s such a cute little place. Bed was very comfortable. Place was clean. My second time staying here. Would stay here again. " [](https://expedia.ca/La-Grange-Hotels-Adorable-Guest-Cabin-In-The-Woods.h93225597.Hotel-Information) ![Best Western Giddings Inn & Suites](//images.trvl-media.com/lodging/4000000/3980000/3972200/3972119/460c006b_y.jpg) ### Best Western Giddings Inn & Suites 10/10 Excellent "The room was very nice.. David was very professional and offered a good breakfast selection.." [](https://expedia.ca/Brenham-Hotels-Best-Western-Giddings-Inn-Suites.h3972119.Hotel-Information) ![Cozy Cottage With a View in La Grange](//images.trvl-media.com/lodging/120000000/119790000/119784000/119783989/b4707b12_y.jpg) ### Cozy Cottage With a View in La Grange 10/10 Excellent "Perfect spot… Right in the middle of all the things we came to do! Great for a trip up to Round Top and Warrenton for antiquing! And also a day trip into Austin! The cottage was cozy and had all the right things to make it feel like home! My daughter and I had a great stay! " [](https://expedia.ca/La-Grange-Hotels-Cozy-Cottage-With-A-View-In-La-Grange.h119783989.Hotel-Information) ![River Valley Motor Inn](//images.trvl-media.com/lodging/1000000/980000/973500/973410/7699e214_y.jpg) ### River Valley Motor Inn 10/10 Excellent "Great" [](https://expedia.ca/Columbus-Hotels-River-Valley-Motor-Inn.h973410.Hotel-Information) ## Find out more about Winchester ## Winchester Guest Houses information | Number of reviews | 54 | | --- | --- | | Accommodation | 5 Guest Houses | | Lowest Price | CA $284 | | Highest Price | CA $333 | ## 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) - 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