Title: 4 Stars Hotels in Winchester, Winsted from CA $253 - Find Cheap Winchester Hotels With 4 Stars | Expedia.ca [Winchester Travel Guide](https://expedia.ca/Winchester.dx553248635975869849)[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)[Flights to Winchester](https://expedia.ca/Cheap-Flights-To-Winchester.d553248635975869849.Travel-Guide-Flights)[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) # 4 Stars Hotels in Winchester, Winsted from CA $253 ![](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 availability on Winchester 4 Star Hotels Tonight [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-10-13&endDate=2025-10-14&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-10-14&endDate=2025-10-15&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-10-24&endDate=2025-10-26&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winchester 4 Star Hotels ![Lunch and dinner served](https://images.trvl-media.com/lodging/19000000/18170000/18166800/18166744/d809cec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/19000000/18170000/18166800/18166744/432bc97c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast for a fee](https://images.trvl-media.com/lodging/19000000/18170000/18166800/18166744/e95e3d06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/19000000/18170000/18166800/18166744/d90b3de9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Delamar West Hartford West Hartford 9.8/10 Exceptional (1003) "Clean and convenient " CA $435 CA $522 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Hartford-Hotels-Delamar-West-Hartford.h18166744.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/5000000/4980000/4978900/4978856/9aa3fa98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/5000000/4980000/4978900/4978856/a8d7410e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/5000000/4980000/4978900/4978856/f2a12d98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/5000000/4980000/4978900/4978856/1a357fc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Litchfield Inn Litchfield 9.0/10 Wonderful (947) "The Litchfield Inn was very nice and quaint! Judy at the Front Desk was amazing and so accommodating. Will definitely stay again." CA $398 CA $458 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Torrington-Hotels-The-Litchfield-Inn.h4978856.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/50000/42300/42279/6326a611.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/50000/42300/42279/5cb24d7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Queen with Sofa Bed](https://images.trvl-media.com/lodging/1000000/50000/42300/42279/c37c5ed2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/1000000/50000/42300/42279/99af973d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Simsbury 1820 House Simsbury Center 9.2/10 Wonderful (998) "The staff was super friendly and accommodating " CA $229 CA $287 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Hartford-Hotels-Simsbury-1820-House.h42279.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5300/5265/7a34507b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/5300/5265/de3a2b5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/10000/5300/5265/7d74995e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![55-inch flat-screen TV with satellite channels, pay movies](https://images.trvl-media.com/lodging/1000000/10000/5300/5265/7baf880a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Hotel Bristol, Connecticut Bristol 9.0/10 Wonderful (1005) "The hotel was great the front desk " CA $220 CA $253 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Hartford-Hotels-DoubleTree-By-Hilton-Hotel-Bristol.h5265.Hotel-Information) ![John Harney Suite](https://images.trvl-media.com/lodging/17000000/16730000/16725200/16725119/04d25b53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/17000000/16730000/16725200/16725119/1ed9f4b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/17000000/16730000/16725200/16725119/e0e21a5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/17000000/16730000/16725200/16725119/cccc903a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The White Hart Salisbury 9.6/10 Exceptional (140) "Amazing stay. Incredible staff, attention to detail. Beyond expectations " CA $461 CA $530 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Torrington-Hotels-The-White-Hart.h16725119.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) ![Room 194, 1 Queen bed, 1 Sofa bed, Courtyard View with balcony](https://images.trvl-media.com/lodging/10000000/9720000/9716100/9716050/d3c12b5c.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) ![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) ### The Old Inn On The Green Great Barrington 9.2/10 Wonderful (90) "Beautiful Inn and outstanding chef" CA $427 CA $515 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Great-Barrington-Hotels-The-Old-Inn-On-The-Green.h9716050.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 14 - Oct 15 [](https://www.expedia.ca/Salisbury-Hotels-9-Academy.h102680999.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/3000000/2880000/2878300/2878272/f9a4c0cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/3000000/2880000/2878300/2878272/81937000.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room dining](https://images.trvl-media.com/lodging/3000000/2880000/2878300/2878272/8684b852.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Fireplace](https://images.trvl-media.com/lodging/3000000/2880000/2878300/2878272/c21f58f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rock Hall Luxe Lodging Winsted 10/10 Exceptional (4) [](https://www.expedia.ca/Winsted-Hotels-Rock-Hall-Luxe-Lodging.h2878272.Hotel-Information) ![House, Multiple Beds, Pool Access, Mountain View (Connecticut Five Bedroom Home) | Private kitchen](https://images.trvl-media.com/lodging/110000000/109010000/109009800/109009785/a864d1b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, Multiple Beds, Pool Access, Mountain View (Connecticut Five Bedroom Home) | Living area](https://images.trvl-media.com/lodging/110000000/109010000/109009800/109009785/5c56478d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/110000000/109010000/109009800/109009785/6105b32f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109010000/109009800/109009785/6c2e14a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ABC Stay - Connecticut Five Bedroom Home New Preston [](https://www.expedia.ca/New-Preston-Hotels-ABC-Stay-Connecticut-Five-Bedroom-Home.h109009785.Hotel-Information) ![](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%2F4Star-Winchester-Hotels.s40-0-d553248635975869849.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F4Star-Winchester-Hotels.s40-0-d553248635975869849.Travel-Guide-Filter-Hotels) ## Explore similar 5-star hotels Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Winchester. ![Mayflower Inn & Spa, Auberge Collection](https://images.trvl-media.com/lodging/1000000/180000/170800/170742/5296f0bf_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Mayflower Inn & Spa, Auberge Collection 118 Woodbury Rd., Washington, CT CA $1,247 CA $1,499 total Nov 4 - Nov 5 includes taxes & fees 9.2/10 Wonderful! (53 reviews) [](https://expedia.ca/Torrington-Hotels-Mayflower-Inn-Spa.h170742.Hotel-Information) ![Troutbeck](https://images.trvl-media.com/lodging/22000000/21770000/21767700/21767645/4a6d4a2e_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Troutbeck 515 Leedsville Rd, Amenia, NY [Get rates](https://expedia.ca/Hotel-Search?startDate=27%2F10%2F2025&endDate=28%2F10%2F2025&selected=21767645&PinnedHotelID=21767645&HadPinnedHotel=true®ionId=553248635975869849) [](https://expedia.ca/Amenia-Hotels-Troutbeck.h21767645.Hotel-Information) ![Las Flores Villa](https://images.trvl-media.com/lodging/71000000/70550000/70549400/70549365/ff59e7a0_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Las Flores Villa 38 Strawberry Ridge Rd, New Preston, CT CA $1,424 CA $2,198 total Oct 15 - Oct 16 includes taxes & fees [](https://expedia.ca/New-Preston-Hotels-Las-Flores-Villa.h70549365.Hotel-Information) Still don't see what you're looking for? [See all properties in Winchester.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=553248635975869849&star=40) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=553248635975869849&star=40&star=40&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=553248635975869849&star=40&star=40&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=553248635975869849&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=553248635975869849&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=553248635975869849&star=40&star=40&amenities=WATER_PARK) 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. ## Top Winchester Hotel Reviews ![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) ![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 If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Winchester are calling your name. Known for providing first-rate service in amazing locations, each of the Winchester 4 Stars hotels lets discerning travelers bask in an unforgettable experience. Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day. It’s all waiting for you at the top four star hotels in Winchester. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Winchester, Winsted, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Winchester hotels with 4 Stars provide everything you need to unwind in style. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [3 Star Hotels in Northford](https://www.expedia.ca/3Star-Northford-Hotels.s30-0-d6004524.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Windsor](https://www.expedia.ca/3Star-Windsor-Hotels.s30-0-d7880.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Beacon Falls](https://www.expedia.ca/4Star-Beacon-Falls-Hotels.s40-0-d6348182.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Coventry Lake](https://www.expedia.ca/4Star-Coventry-Lake-Coventry-Hotels.s40-n553248635976474146-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Durham](https://www.expedia.ca/4Star-Durham-Hotels.s40-0-d6004516.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Shelton](https://www.expedia.ca/4Star-Shelton-Hotels.s40-0-d9795.Travel-Guide-Filter-Hotels) - 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