Title: Winchester Inns from CA $319 | 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 Inns in Winchester from CA $319 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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=INN&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=INN&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=INN&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=INN&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winchester Inns ![Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/18000000/17280000/17278300/17278254/40c2786c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/18000000/17280000/17278300/17278254/282b9f8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/18000000/17280000/17278300/17278254/417c3a12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/18000000/17280000/17278300/17278254/ebb74cc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cornwall Inn and Lodge Cornwall Bridge 9.2/10 Wonderful (148) "This inn was very quaint and welcoming. It was a nice inn for the value. " CA $277 CA $319 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Torrington-Hotels-Cornwall-Inn-And-Lodge.h17278254.Hotel-Information) ![Room 191, 1 Queen Bed, 1 Single Bed, 1 Sofa Bed](https://images.trvl-media.com/lodging/10000000/9720000/9716100/9716050/90de0046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/10000000/9720000/9716100/9716050/8a8cd518.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/10000000/9720000/9716100/9716050/de957a5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room 191, 1 Queen Bed, 1 Single Bed, 1 Sofa Bed](https://images.trvl-media.com/lodging/10000000/9720000/9716100/9716050/267d369d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Old Inn On The Green Great Barrington 9.2/10 Wonderful (90) "Beautiful Inn and outstanding chef" CA $426 CA $513 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Great-Barrington-Hotels-The-Old-Inn-On-The-Green.h9716050.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=2025-10-22&endDate=2025-10-23®ionId=553248635975869849&adults=2&lodging=INN&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-Inns.d553248635975869849-aaInns.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Inns.d553248635975869849-aaInns.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![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) ![Avon Old Farms Hotel](//images.trvl-media.com/lodging/1000000/10000/2700/2635/d997675e_y.jpg) ### Avon Old Farms Hotel 10/10 Excellent "Older facility but very well maintained. Lovely nreakfast" [](https://expedia.ca/Hartford-Hotels-Avon-Old-Farms-Hotel.h2635.Hotel-Information) ![Simsbury 1820 House](//images.trvl-media.com/lodging/1000000/50000/42300/42279/6326a611_y.jpg) ### Simsbury 1820 House 10/10 Excellent "New England charm!" [](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 "We enjoyed our stay at the Litchfield Inn and hope to return soon. The Inn is well appointed, clean and inviting . Loved all of the comfy gathering areas " [](https://expedia.ca/Torrington-Hotels-The-Litchfield-Inn.h4978856.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) ![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 "Great Experience " [](https://expedia.ca/Bristol-Hotels-Home2-Suites-By-Hilton-Bristol.h94946614.Hotel-Information) ![Simsbury Inn](//images.trvl-media.com/lodging/1000000/20000/16800/16756/ceb52ab8_y.jpg) ### Simsbury Inn 10/10 Excellent "I loved my stay there. Beautiful rooms, the hot tub was great! Breakfast was decent but there are plenty of food options around town if you want something better!" [](https://expedia.ca/Weatogue-Hotels-Simsbury-Inn.h16756.Hotel-Information) ![Delamar West Hartford](//images.trvl-media.com/lodging/19000000/18170000/18166800/18166744/d809cec2_y.jpg) ### Delamar West Hartford 10/10 Excellent "always a great stay at a great hotel chain!" [](https://expedia.ca/Hartford-Hotels-Delamar-West-Hartford.h18166744.Hotel-Information) ## Find out more about Winchester ## Winchester Inns information | Number of reviews | 236 | | --- | --- | | Accommodation | 2 Inns | | Lowest Price | CA $319 | | Highest Price | CA $513 | ## 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) - [Farmstay in Colebrook](https://www.expedia.ca/Colebrook-Agritourism.d6125522-aaAgritourism.Travel-Guide-Accommodation) - 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