Title: Winchester Guest Houses from CA $263 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d6056879.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d6056879.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.ca/Cheap-Flights-To-Winchester.d6056879.Travel-Guide-Flights)[Things to do in Winchester](https://expedia.ca/Things-To-Do-In-Winchester.d6056879.Travel-Guide-Activities)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d6056879.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d6056879.Destination-Travel-Guides) ![](https://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6.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 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-01-23&endDate=2026-01-25&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-01-30&endDate=2026-02-01&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-02-13&endDate=2026-02-15&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-03-13&endDate=2026-03-15&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester guest houses ![Garden](https://images.trvl-media.com/lodging/91000000/90760000/90758600/90758569/dad200f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/91000000/90760000/90758600/90758569/e3f5e91d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/91000000/90760000/90758600/90758569/cd47970a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooster Room](https://images.trvl-media.com/lodging/91000000/90760000/90758600/90758569/230f2f7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Briar Patch Bed & Breakfast Inn [](https://www.expedia.ca/Middleburg-Hotels-Briar-Patch-Bed-Breakfast-Inn.h90758569.Hotel-Information) Middleburg 8.0/10 Very good (11 reviews) "A lovely setting...breakfast was fantastic...cook was charming & everything was tasty & homemade. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) david [](https://www.expedia.ca/Middleburg-Hotels-Briar-Patch-Bed-Breakfast-Inn.h90758569.Hotel-Information) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78120000/78111100/78111003/b77f2651.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/79000000/78120000/78111100/78111003/9ea45e22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/79000000/78120000/78111100/78111003/69b3c9fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/79000000/78120000/78111100/78111003/e09bb34f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Chickadee Room at Harpers Ferry Guest House [](https://www.expedia.ca/Harpers-Ferry-Hotels-The-Chickadee-Room-At-Harpers-Ferry-Guest-House.h78111003.Hotel-Information) Harpers Ferry 10/10 Exceptional (14 reviews) "The homey, comfortable atmosphere and the location are stand-outs of this charming, B&B. Great hosts!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason [](https://www.expedia.ca/Harpers-Ferry-Hotels-The-Chickadee-Room-At-Harpers-Ferry-Guest-House.h78111003.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/40000000/39540000/39532100/39532065/a816723a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/40000000/39540000/39532100/39532065/a4b6c89d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/40000000/39540000/39532100/39532065/3166dbe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/40000000/39540000/39532100/39532065/c4008514.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment [](https://www.expedia.ca/Marshall-Hotels-Private-Unicorn-Hollow-AptWineries-Twilight-PoloMiddleburg.h39532065.Hotel-Information) The Plains 10/10 Exceptional (6 reviews) "The hosts are amazing! So accommodating and welcoming. The place is something special. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) AMY B. CA $344 CA $560 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Marshall-Hotels-Private-Unicorn-Hollow-AptWineries-Twilight-PoloMiddleburg.h39532065.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/79000000/78120000/78111000/78110996/96995dbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78120000/78111000/78110996/d1f14fea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/79000000/78120000/78111000/78110996/ce5c4db6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/79000000/78120000/78111000/78110996/fdf127d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Bluebird Suite at Harpers Ferry Guest House [](https://www.expedia.ca/Harpers-Ferry-Hotels-The-Bluebird-Suite-At-Harpers-Ferry-Guest-House.h78110996.Hotel-Information) Harpers Ferry 10/10 Exceptional (58 reviews) "It was very clean and well maintained. I enjoyed the fire pit on the porch. The hosts communicated very well" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $174 CA $263 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Harpers-Ferry-Hotels-The-Bluebird-Suite-At-Harpers-Ferry-Guest-House.h78110996.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/79000000/78120000/78111100/78111011/ceebb271.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78120000/78111100/78111011/1823e7e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/79000000/78120000/78111100/78111011/eac83f67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/79000000/78120000/78111100/78111011/a1f7a658.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Goldfinch Suite at Harpers Ferry Guest House [](https://www.expedia.ca/Harpers-Ferry-Hotels-The-Goldfinch-Suite-At-Harpers-Ferry-Guest-House.h78111011.Hotel-Information) Harpers Ferry 10/10 Exceptional (54 reviews) "Great location ,Will stay agin." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin L. CA $174 CA $263 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Harpers-Ferry-Hotels-The-Goldfinch-Suite-At-Harpers-Ferry-Guest-House.h78111011.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/79000000/78120000/78111000/78110998/49544261.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78120000/78111000/78110998/3a946088.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/79000000/78120000/78111000/78110998/659c2aed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/79000000/78120000/78111000/78110998/1368d46b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Cardinal Suite at Harpers Ferry Guest House [](https://www.expedia.ca/Harpers-Ferry-Hotels-The-Cardinal-Suite-At-Harpers-Ferry-Guest-House.h78110998.Hotel-Information) Harpers Ferry 10/10 Exceptional (21 reviews) "Lovely room, easy check in/out, and thoughtful amenities. Would absolutely stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth CA $187 CA $279 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Harpers-Ferry-Hotels-The-Cardinal-Suite-At-Harpers-Ferry-Guest-House.h78110998.Hotel-Information) ![Premier Villa, 1 King Bed, Mountain View | Terrace/patio](https://images.trvl-media.com/lodging/14000000/13400000/13391000/13390991/a36aa267.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Romantic Room, 1 King Bed, Non Smoking (The Cottage)](https://images.trvl-media.com/lodging/14000000/13400000/13391000/13390991/4c371a72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/14000000/13400000/13391000/13390991/c8efbec6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/14000000/13400000/13391000/13390991/445f5296.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### White Moose Inn [](https://www.expedia.ca/Washington-Hotels-White-Moose-Inn.h13390991.Hotel-Information) Washington 9.8/10 Exceptional (149 reviews) "Staff is wonderful. The whole 1st floor would make Marie Kondo proud! Breakfast is excellent. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Judy [](https://www.expedia.ca/Washington-Hotels-White-Moose-Inn.h13390991.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=2026-01-29&endDate=2026-01-30®ionId=6056879&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.d6056879-aaGuestHouses.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Guest-Houses.d6056879-aaGuestHouses.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Microtel Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657_y.jpg) ### Microtel Inn & Suites by Wyndham Winchester 10/10 Excellent "This is our number one spot to stay in in Winchester. The location is perfect. Rooms are clean and modern." [](https://expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) ![Hampton Inn Winchester-University/Mall Area](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68_y.jpg) ### Hampton Inn Winchester-University/Mall Area 10/10 Excellent "Pet friendly and they provided a goodie bag for my dog - very welcoming." [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.Hotel-Information) ![TRU By Hilton Winchester](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/b9c1387b_y.jpg) ### TRU By Hilton Winchester 10/10 Excellent "Such a nice hotel! The lobby is so accommodating and clean, the breakfast was delicious. The pool was clean and warm. My daughter loved it. The room was spacious and clean. Would definitely stay again the price was great " [](https://expedia.ca/Winchester-Hotels-TRU-By-Hilton-Winchester.h39493421.Hotel-Information) ![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/9d44a9b1_y.jpg) ### Travelodge by Wyndham Winchester 10/10 Excellent "C'était propre et tranquille" [](https://expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![Hampton Inn Martinsburg](https://images.trvl-media.com/lodging/1000000/70000/63100/63064/835cd022_y.jpg) ### Hampton Inn Martinsburg 10/10 Excellent "Great beds and pillows." [](https://expedia.ca/Martinsburg-Hotels-Hampton-Inn-Martinsburg.h63064.Hotel-Information) ![Hampton Inn Winchester N/Conference Center, VA](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/cba33bb0_y.jpg) ### Hampton Inn Winchester N/Conference Center, VA 10/10 Excellent "Just perfect in every way!" [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-NConference-Center.h424883.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_y.jpg) ### La Quinta Inn & Suites by Wyndham Winchester 10/10 Excellent "Clean room; really comfortable bed. Great staff " [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![SpringHill Suites by Marriott Winchester](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/193cda05_y.jpg) ### SpringHill Suites by Marriott Winchester 10/10 Excellent "Good" [](https://expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) ![APM Inn & Suites](https://images.trvl-media.com/lodging/30000000/29420000/29415600/29415558/782daa80_y.jpg) ### APM Inn & Suites 10/10 Excellent "Clean rooms great staff always willing to help and accommodate top shelf customer service" [](https://expedia.ca/Winchester-Hotels-APM-Inn-Suites.h29415558.Hotel-Information) ## Find out more about Winchester ## Winchester Guest Houses information | Number of reviews | 313 | | ----------------- | --------------- | | Accommodation | 19 Guest Houses | | Lowest Price | CA $263 | | Highest Price | CA $560 | ## Frequently asked questions ### What is the nightly rate for a guest house in Winchester? ### What's the difference between a Winchester guest house and a B&B? ## Explore a world of travel with Expedia - 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[Appleland Sports Center ](https://www.expedia.ca/Appleland-Sports-Center-Stephens-City.d553248621587477489.Vacation-Attraction) - [Jim Barnett Park ](https://www.expedia.ca/Jim-Barnett-Park-Winchester.d6164028.Vacation-Attraction) - [Visit Millwood ](https://www.expedia.ca/Millwood.dx3000460156) - [Book Guest Houses in Winchester on Expedia.com ](https://www.expedia.com/Winchester-Guest-Houses.d6056879-aaGuestHouses.Travel-Guide-Accommodation)