Title: Winchester B&B: Find the Best Bed and Breakfast from CA $217 | 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) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=553248635975876131&startDate=2026-01-30&endDate=2026-02-01&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248635975876131&startDate=2026-02-06&endDate=2026-02-08&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=553248635975876131&startDate=2026-02-20&endDate=2026-02-22&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=553248635975876131&startDate=2026-03-20&endDate=2026-03-22&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester bed & breakfast ![Property grounds](https://images.trvl-media.com/lodging/97000000/96900000/96893900/96893825/3e82bd01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96900000/96893900/96893825/46dda316.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96900000/96893900/96893825/c50b923c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96900000/96893900/96893825/560c5f15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Vagabond Room - Wander Inn [](https://www.expedia.ca/Round-Top-Hotels-The-Vagabond-Room-Wander-Inn.h96893825.Hotel-Information) Round Top 10/10 Exceptional (1 review) "Beautiful sunsets and sunrise. Relaxing venue after a hard day of antiquing. Life on the ranch was never more delightful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tanya M. CA $270 CA $512 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Round-Top-Hotels-The-Vagabond-Room-Wander-Inn.h96893825.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96900000/96893900/96893821/f250d4a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96900000/96893900/96893821/614fc039.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96900000/96893900/96893821/0462d577.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace, books, music library](https://images.trvl-media.com/lodging/97000000/96900000/96893900/96893821/33d3693a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Rambler Room - Wander Inn [](https://www.expedia.ca/Round-Top-Hotels-The-Rambler-Room-Wander-Inn.h96893821.Hotel-Information) Round Top CA $270 CA $512 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Round-Top-Hotels-The-Rambler-Room-Wander-Inn.h96893821.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96900000/96893900/96893823/43261980.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96900000/96893900/96893823/3aaae612.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96900000/96893900/96893823/630ca0f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace, books, music library](https://images.trvl-media.com/lodging/97000000/96900000/96893900/96893823/c211ee73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Thunderbird Room - Wander Inn [](https://www.expedia.ca/Round-Top-Hotels-The-Thunderbird-Room-Wander-Inn.h96893823.Hotel-Information) Round Top 8.0/10 Very good (2 reviews) "Fantastic ! Close to everything and easy to find.Cool furnishings Loved the porch watching the cows to relax!:)" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rose W. CA $270 CA $512 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Round-Top-Hotels-The-Thunderbird-Room-Wander-Inn.h96893823.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/97000000/96900000/96893900/96893809/8932655f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96900000/96893900/96893809/bb262472.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96900000/96893900/96893809/6b60df12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96900000/96893900/96893809/cff3b8b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Stardust Room - Wander Inn [](https://www.expedia.ca/Round-Top-Hotels-The-Stardust-Room-Wander-Inn.h96893809.Hotel-Information) Round Top 10/10 Exceptional (2 reviews) "Great property & location!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Megan N. CA $270 CA $512 total includes taxes & fees Feb 16 - Feb 17 [](https://www.expedia.ca/Round-Top-Hotels-The-Stardust-Room-Wander-Inn.h96893809.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96900000/96893900/96893819/8bdd51b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace, books, music library](https://images.trvl-media.com/lodging/97000000/96900000/96893900/96893819/2179309a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96900000/96893900/96893819/f9932acb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96900000/96893900/96893819/f7148505.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Delight Room - Wander Inn [](https://www.expedia.ca/Round-Top-Hotels-Country-Delight-Room-Wander-Inn.h96893819.Hotel-Information) Round Top 10/10 Exceptional (2 reviews) "We truly enjoyed our stay! Bed, linens and pillows were very comfortable. The property is beautiful! I’ve been wanting to stay here for quite a while and my husband reserved it for Mother’s Day. Exceeded my expectations!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sallie H. CA $270 CA $512 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Round-Top-Hotels-Country-Delight-Room-Wander-Inn.h96893819.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96900000/96893900/96893806/c496bb35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/97000000/96900000/96893900/96893806/5ff5141b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96900000/96893900/96893806/51865676.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96900000/96893900/96893806/ccc8008f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Bandita Room - Wander Inn [](https://www.expedia.ca/Round-Top-Hotels-The-Bandita-Room-Wander-Inn.h96893806.Hotel-Information) Round Top CA $270 CA $512 total includes taxes & fees Feb 16 - Feb 17 [](https://www.expedia.ca/Round-Top-Hotels-The-Bandita-Room-Wander-Inn.h96893806.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/97000000/96900000/96893900/96893804/daea484c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96900000/96893900/96893804/c8198690.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, jetted tub, rainfall showerhead, hair dryer](https://images.trvl-media.com/lodging/97000000/96900000/96893900/96893804/3ff5f362.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96900000/96893900/96893804/4aa23717.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wanderlust Room - Wander Inn [](https://www.expedia.ca/Round-Top-Hotels-The-Wanderlust-Room-Wander-Inn.h96893804.Hotel-Information) Round Top CA $270 CA $512 total includes taxes & fees Feb 16 - Feb 17 [](https://www.expedia.ca/Round-Top-Hotels-The-Wanderlust-Room-Wander-Inn.h96893804.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/97000000/96900000/96893900/96893812/cf93c506.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96900000/96893900/96893812/48d58fbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96900000/96893900/96893812/973093ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96900000/96893900/96893812/de64a558.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wild Blue Yonder Room - Wander Inn [](https://www.expedia.ca/Round-Top-Hotels-The-Wild-Blue-Yonder-Room-Wander-Inn.h96893812.Hotel-Information) Round Top CA $270 CA $512 total includes taxes & fees Feb 16 - Feb 17 [](https://www.expedia.ca/Round-Top-Hotels-The-Wild-Blue-Yonder-Room-Wander-Inn.h96893812.Hotel-Information) ![Room, Private Bathroom (Katy Tower) | Bathroom](https://images.trvl-media.com/lodging/2000000/1160000/1153700/1153604/89b81894.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Garden Cottage | Terrace/patio](https://images.trvl-media.com/lodging/2000000/1160000/1153700/1153604/de95496a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![32-inch Smart TV with cable channels, TV, streaming services](https://images.trvl-media.com/lodging/2000000/1160000/1153700/1153604/823dfc86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1160000/1153700/1153604/07e11d51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Katy House Bed and Breakfast [](https://www.expedia.ca/Columbus-Hotels-Katy-House-Bed-And-Breakfast.h1153604.Hotel-Information) Downtown Smithville 9.2/10 Wonderful (409 reviews) "Great breakfast and staycation " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shelby CA $190 CA $217 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Columbus-Hotels-Katy-House-Bed-And-Breakfast.h1153604.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=2026-02-04&endDate=2026-02-05®ionId=553248635975876131&adults=2&lodging=BED_AND_BREAKFAST&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-Bed-And-Breakfast.d553248635975876131-aaBedAndBreakfast.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Bed-And-Breakfast.d553248635975876131-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Executive inn & Suites](https://images.trvl-media.com/lodging/112000000/111850000/111843500/111843422/34e99ede_y.jpg) ### Executive inn & Suites 10/10 Excellent "Staff very nice and courteous." [](https://expedia.ca/La-Grange-Hotels-Executive-Inn-Suites.h111843422.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 "Wonderful location, property was clean, very cozy" [](https://expedia.ca/La-Grange-Hotels-Adorable-Guest-Cabin-In-The-Woods.h93225597.Hotel-Information) ![Pinehaven Luxury Glamping](https://images.trvl-media.com/lodging/94000000/93230000/93223900/93223882/b7fa9890_y.jpg) ### Pinehaven Luxury Glamping 10/10 Excellent "Absolutely exceptional stayThis cabin was truly outstanding in every possible way. The location is breathtaking, completely surrounded by nature, offering total privacy and a sense of peace that is hard to find. It felt like a perfect escape from daily life.The amenities were excellent and thoughtfully designed, making the entire experience comfortable, cozy, and special. Everything was spotless and well maintained.If you’re looking for a romantic getaway, this place is simply perfect. Quiet, private, intimate, and deeply connected to nature. We couldn’t have asked for a better experience.Highly recommended — we would absolutely return." [](https://expedia.ca/La-Grange-Hotels-Pinehaven-Luxury-Glamping.h93223882.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 "Room was spotless, staff was courteous." [](https://expedia.ca/Giddings-Hotels-Studio-6-Giddings.h119074593.Hotel-Information) ![The Cottage, A Tranquil Pet-Friendly Retreat on 42 Acres at Lost Pines Shire](https://images.trvl-media.com/lodging/28000000/27120000/27117700/27117611/d2956a4d_y.jpg) ### The Cottage, A Tranquil Pet-Friendly Retreat on 42 Acres at Lost Pines Shire 10/10 Excellent "Second time to stay here, we love the land and location. Peaceful getaway" [](https://expedia.ca/Paige-Hotels-The-Cottage.h27117611.Hotel-Information) ![Angeltom Cabin & RV:20 Acre Woods - >16 pip + Jacuzzi + treehouse + UTV + 2ponds](https://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 "We had an amazing time. It is a great place with a lit to do around the house. The house is clean and the owners are very nice people. The answered questions within minutes. We are planning another trip to go again. " [](https://expedia.ca/Columbus-Hotels-Angeltom-Cabin-RV-10-Acre-Woods-Sleeps-Up-To-14-People.h22343739.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 "Second time staying here. Very friendly and helpful staff. Room was clean, bed was comfy." [](https://expedia.ca/Columbus-Hotels-Best-Western-La-Grange-Inn-Suites.h1522868.Hotel-Information) ![Farmstead Round Top](https://images.trvl-media.com/lodging/45000000/44360000/44357400/44357397/b004d1bf_y.jpg) ### Farmstead Round Top 10/10 Excellent "Responsive to my requests and mind when answering my questions." [](https://expedia.ca/Brenham-Hotels-Farmstead-Round-Top.h44357397.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 "Room very clean! Plenty towels Front desk person so nice! " [](https://expedia.ca/Columbus-Hotels-River-Valley-Motor-Inn.h973410.Hotel-Information) ## Find out more about Winchester ## Winchester B&B information | Number of reviews | 94 | | ----------------- | ------- | | Accommodation | 2 B&B | | Lowest Price | CA $217 | | Highest Price | CA $512 | ## Frequently asked questions ### Searching for B&Bs in Winchester? ### Why consider B&Bs instead of traditional hotels? ### What are the best bed and breakfasts in Winchester? ### When is the best time to stay at a B&B in Winchester? ### How can I get to and around Winchester? ## 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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