Title: Winchester Guest Houses from CA $267 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d183815.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d183815.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d183815.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d183815.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 [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=183815&startDate=2026-02-13&endDate=2026-02-15&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=183815&startDate=2026-02-20&endDate=2026-02-22&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=183815&startDate=2026-03-06&endDate=2026-03-08&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=183815&startDate=2026-04-03&endDate=2026-04-05&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester guest houses ![Outdoor spa tub](https://images.trvl-media.com/lodging/91000000/90770000/90764700/90764643/be61c022.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90770000/90764700/90764643/04625cc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90770000/90764700/90764643/3341f262.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90770000/90764700/90764643/41e4e82e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Meadowview Guest House [](https://www.expedia.ca/Hillsboro-Hotels-Meadowview-Guest-House.h90764643.Hotel-Information) Hillsboro 10/10 Exceptional (22 reviews) "I was out there for a wedding and this place was great for a weekend trip." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) L CA $160 CA $267 total includes taxes & fees Feb 10 - Feb 11 [](https://www.expedia.ca/Hillsboro-Hotels-Meadowview-Guest-House.h90764643.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=2026-02-22&endDate=2026-02-23®ionId=183815&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.d183815-aaGuestHouses.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Guest-Houses.d183815-aaGuestHouses.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Cozy private getaway built for couples to reconnect !! ](https://images.trvl-media.com/lodging/100000000/99850000/99846400/99846345/c709cc75_y.jpg) ### Cozy private getaway built for couples to reconnect !! 10/10 Excellent "Great place to get away. House was clean, nicely setup, and as good or better than the pictures! Make sure you take note that there isn’t internet service. Hope to return. " [](https://expedia.ca/West-Union-Hotels-Cozy-Private-Getaway-Built-For-Couples-To-Reconnect.h99846345.Hotel-Information) ![Get away from it all! Restored 1800 log cabin on 40 acres - NO cleaning fee!](https://images.trvl-media.com/lodging/34000000/33950000/33949400/33949345/ce32c6b5_y.jpg) ### Get away from it all! Restored 1800 log cabin on 40 acres - NO cleaning fee! 10/10 Excellent "The cabin was totally unique and provided an amazing experience. Everything was well planned with clear instructions on location, use of the fireplace, all the appliances and kitchen equipment. The cabin was very clean well kept and it exceeded my expectations. The host left a personal note and provided contact number if anything was needed. The cabin is located in a remote location which adds to its charm. The cabin is full of very interesting unique 1800s log construction with modern conveniences. The cabin is well designed and build with care. It cabin will not disappoint. It is a wonderful place." [](https://expedia.ca/Blue-Creek-Hotels-Get-Away-From-It-All-Restored-1800-Log-Cabin-Modern-Amenities-40-Private-Acres.h33949345.Hotel-Information) ![Days Inn by Wyndham Maysville Kentucky](https://images.trvl-media.com/lodging/1000000/30000/25500/25466/032fdf94_y.jpg) ### Days Inn by Wyndham Maysville Kentucky 10/10 Excellent "We left before breakfast was served. Great room; very clean, easy access. Bed was comfortable but the pillows were a bit too hard and small. They were not full size. " [](https://expedia.ca/Maysville-Hotels-Days-Inn-By-Wyndham-Maysville-Kentucky.h25466.Hotel-Information) ![Beverly hills inn](https://images.trvl-media.com/lodging/109000000/108730000/108721700/108721615/2ca35418_y.jpg) ### Beverly hills inn 10/10 Excellent "Everything good " [](https://expedia.ca/Aberdeen-Hotels-Beverly-Hills-Inn.h108721615.Hotel-Information) ![McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events](https://images.trvl-media.com/lodging/92000000/91850000/91842200/91842120/46b8330a_y.jpg) ### McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events 10/10 Excellent "The place was so great. We loved it and everything was better than what we expected. " [](https://expedia.ca/Williamsburg-Hotels-McKeever-Mansion-9.h91842120.Hotel-Information) ![Days Inn by Wyndham Hillsboro](https://images.trvl-media.com/lodging/1000000/50000/42800/42776/0ea60812_y.jpg) ### Days Inn by Wyndham Hillsboro 10/10 Excellent "We stayed Christmas night. My son LOVED the perfect bed and my mom fell asleep immediately on (her needed choice) the couch because everything was so inviting. BUT by far, the most wonderful thing was the courteous front desk clerk. He helped my mother, helped with pictures, helped with my great-niece’s little one and offered great solutions for a way for us to have Christmas. We will be forever grateful." [](https://expedia.ca/Hillsboro-Hotels-Days-Inn-By-Wyndham-Hillsboro.h42776.Hotel-Information) ![Paragon Inn Hillsboro](https://images.trvl-media.com/lodging/3000000/2980000/2974700/2974636/8a89f8e6_y.jpg) ### Paragon Inn Hillsboro 10/10 Excellent "Clean " [](https://expedia.ca/Hillsboro-Hotels-Paragon-Inn-Hillsboro.h2974636.Hotel-Information) ![Countryside Inn & Suites](https://images.trvl-media.com/lodging/1000000/330000/327900/327877/2c0e7fee_y.jpg) ### Countryside Inn & Suites 10/10 Excellent "Clean room! Good breakfast" [](https://expedia.ca/Hillsboro-Hotels-Countryside-Inn-Suites.h327877.Hotel-Information) ![Peaceful cabin with spectacular river and scenic views.](https://images.trvl-media.com/lodging/106000000/105570000/105562300/105562236/fbed2d1d_y.jpg) ### Peaceful cabin with spectacular river and scenic views. 10/10 Excellent "This cabin was a great weekend getaway. The cabin itself is very comfortable and the views are spectacular. Christopher is the best host we have had the pleasure of working with. He had the cabin stocked with everything you could want. Would rent from Christopher, at this cabin or anywhere else, again." [](https://expedia.ca/Aberdeen-Hotels-Peaceful-Cabin-With-Spectacular-River-And-Scenic-Views-Along-With-Great-Sunsets.h105562236.Hotel-Information) ## Find out more about Winchester ## Winchester Guest Houses information | Number of reviews | 22 | | ----------------- | -------------- | | Accommodation | 1 Guest Houses | | Lowest Price | CA $267 | | Highest Price | CA $267 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [5 Star Hotels in Peebles ](https://www.expedia.ca/5Star-Peebles-Hotels.s50-0-d6195740.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Sardinia ](https://www.expedia.ca/5Star-Sardinia-Hotels.s50-0-d553248634983507551.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Aberdeen ](https://www.expedia.ca/Aberdeen-Hotels-Cheap-Hotels.0-0-d6344064-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Aberdeen ](https://www.expedia.ca/Aberdeen-Hotels-Hotel-With-Pool.0-0-d6344064-tHotelwithPool.Travel-Guide-Filter-Hotels) - 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