Title: Winchester Guest Houses from CA $370 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d553248635975869849.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d553248635975869849.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d553248635975869849.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d553248635975869849.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 $370 ![](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 [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winchester Guest Houses ![Interior](https://images.trvl-media.com/lodging/97000000/96740000/96735100/96735071/e5470afd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/97000000/96740000/96735100/96735071/0fbc615e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video-game console, Netflix, books](https://images.trvl-media.com/lodging/97000000/96740000/96735100/96735071/1f8b1f0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96740000/96735100/96735071/179fbbac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A Homey Heaven - Modern, Pet-Friendly, Gaming, Full Kitchen and more. Bristol 9.6/10 Exceptional (10) "It's a fun, funky little place, that had everything we needed. " CA $245 CA $521 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Bristol-Hotels-Cozy-Suite-For-Quick-Getaways-Pet-Friendly.h96735071.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/20000000/19820000/19812300/19812250/beddc5d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/20000000/19820000/19812300/19812250/ab7a0a06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/20000000/19820000/19812300/19812250/9e5b89dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/20000000/19820000/19812300/19812250/bee8460a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A European Country Getaway ~ 1930s Stone Cottage In Connecticut! Granby 10/10 Exceptional (90) "Nice Area. Stone cottage rocks!" CA $210 CA $370 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/North-Granby-Hotels-A-European-Country-Getaway-1930s-Stone-Cottage-In-Connecticut.h19812250.Hotel-Information) ![The Parlor Suite](https://images.trvl-media.com/lodging/103000000/102690000/102681000/102680999/b4671c20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Loft Suite | Terrace/patio](https://images.trvl-media.com/lodging/103000000/102690000/102681000/102680999/7bbc5c67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Parlor Suite | Private kitchen](https://images.trvl-media.com/lodging/103000000/102690000/102681000/102680999/b8c74868.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Loft Suite | In-room dining](https://images.trvl-media.com/lodging/103000000/102690000/102681000/102680999/w5552h4162x0y0-c20c0fd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 9 Academy Salisbury 8.6/10 Excellent (7) "The Loft was so beautifully decorated and every detail was perfect. " CA $692 CA $795 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Salisbury-Hotels-9-Academy.h102680999.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=2025-10-26&endDate=2025-10-27®ionId=553248635975869849&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.d553248635975869849-aaGuestHouses.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Guest-Houses.d553248635975869849-aaGuestHouses.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Avon Old Farms Hotel](//images.trvl-media.com/lodging/1000000/10000/2700/2635/d997675e_y.jpg) ### Avon Old Farms Hotel 10/10 Excellent "Breakfast was really good. They have great espresso machines " [](https://expedia.ca/Hartford-Hotels-Avon-Old-Farms-Hotel.h2635.Hotel-Information) ![Home2 Suites by Hilton Bristol](//images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/74bd7e00_y.jpg) ### Home2 Suites by Hilton Bristol 10/10 Excellent "Has EV charging which is what we needed" [](https://expedia.ca/Bristol-Hotels-Home2-Suites-By-Hilton-Bristol.h94946614.Hotel-Information) ![DoubleTree by Hilton Hotel Bristol, Connecticut](//images.trvl-media.com/lodging/1000000/10000/5300/5265/7a34507b_y.jpg) ### DoubleTree by Hilton Hotel Bristol, Connecticut 10/10 Excellent "Very Clean " [](https://expedia.ca/Hartford-Hotels-DoubleTree-By-Hilton-Hotel-Bristol.h5265.Hotel-Information) ![Simsbury 1820 House](//images.trvl-media.com/lodging/1000000/50000/42300/42279/6326a611_y.jpg) ### Simsbury 1820 House 10/10 Excellent "Fun history. Friendly staff. Good food." [](https://expedia.ca/Hartford-Hotels-Simsbury-1820-House.h42279.Hotel-Information) ![The Litchfield Inn](//images.trvl-media.com/lodging/5000000/4980000/4978900/4978856/9aa3fa98_y.jpg) ### The Litchfield Inn 10/10 Excellent "Upscale. Clean and quiet. " [](https://expedia.ca/Torrington-Hotels-The-Litchfield-Inn.h4978856.Hotel-Information) ![Extended Stay America Suites Hartford Farmington](//images.trvl-media.com/lodging/1000000/160000/151100/151013/02939ae3_y.jpg) ### Extended Stay America Suites Hartford Farmington 10/10 Excellent "I loved my spacious room, kitchen facilities, comfy bed, easy parking. The staff was friendly and helpful, but what I liked best was the feeling of being in my own space, not a hotel. " [](https://expedia.ca/Hartford-Hotels-Extended-Stay-America-Suites-Hartford-Farmington.h151013.Hotel-Information) ![The Farmington Inn & Suites](//images.trvl-media.com/lodging/1000000/20000/10200/10185/1c89931a_y.jpg) ### The Farmington Inn & Suites 10/10 Excellent "Clean good description as given in app" [](https://expedia.ca/Hartford-Hotels-The-Farmington-Inn-Suites.h10185.Hotel-Information) ![Blackberry River Inn](//images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/50a90cdd_y.jpg) ### Blackberry River Inn 10/10 Excellent "At more than 250 years old, the BRI is showing a bit of wear around the edges, but remains elegant and comfortable. Our lovely suite (larger than our NYC apartment) was comfortable and well-appointed and the staff could not have been more friendly and attentive. its a;lso a beautiful corner of the world, with rolling, wooded hills and fine dining scattered across the countyrside." [](https://expedia.ca/Norfolk-Hotels-Blackberry-River-Inn.h95991149.Hotel-Information) ![Sheraton Hartford Hotel at Bradley Airport](//images.trvl-media.com/lodging/1000000/10000/4700/4632/c8edc11d_y.jpg) ### Sheraton Hartford Hotel at Bradley Airport 10/10 Excellent "Rooms appeared to be recently renovated. Front desk staff were excellent." [](https://expedia.ca/Hartford-Hotels-Sheraton-Hartford-Hotel-At-Bradley-Airport.h4632.Hotel-Information) ## Find out more about Winchester ## Winchester Guest Houses information | Number of reviews | 97 | | --- | --- | | Accommodation | 6 Guest Houses | | Lowest Price | CA $370 | | Highest Price | CA $795 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Business Hotels in Barkhamsted](https://www.expedia.ca/Barkhamsted-Hotels-Business-Hotel.0-0-d6359343-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Barkhamsted](https://www.expedia.ca/Barkhamsted-Hotels-Cheap-Hotels.0-0-d6359343-tCheapHotels.Travel-Guide-Filter-Hotels) - [Apartments in City Meadow Boardwalk](https://www.expedia.ca/City-Meadow-Boardwalk-Apartments.d903594079282372608-aaApartments.Travel-Guide-Accommodation) - [Cottages in City Meadow Boardwalk](https://www.expedia.ca/City-Meadow-Boardwalk-Cottages.d903594079282372608-aaCottages.Travel-Guide-Accommodation) - 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