Title: Book the Best Winchester LUXURY Hotels - Upscale Hotels in Winchester, CT | 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://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find luxury hotels in Winchester, CT ![](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 Luxury Hotels Tonight [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-10-14&endDate=2025-10-15&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-10-15&endDate=2025-10-16&adults=2&propertyStyle=LUXURY&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&propertyStyle=LUXURY&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&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winchester Luxury Hotels ## Find out more about Winchester ### Winchesterand its attractions for luxury travelers Nestled in the picturesque Litchfield County, Winchester, Connecticut offers a blend of natural beauty and refined leisure ideal for luxury travellers. Begin your exploration at the stunning Lake Winchester, where you can indulge in private yacht rentals or serene paddleboarding amidst breathtaking views. The nearby Torrington Country Club boasts an exquisite golf course, perfect for those looking to sharpen their swing while enjoying the tranquil surroundings. Art enthusiasts will appreciate the Warner Theatre, a historic venue hosting a variety of high-calibre performances, from live music to theatrical productions, ensuring a cultured evening out. For a touch of adventure, the scenic hiking trails of the nearby Barkhamsted Reservoir offer both challenging paths and leisurely strolls, all set against a backdrop of stunning foliage. When it comes to accommodation, the charming area around Main Street provides a selection of boutique hotels that promise personalised service and lavish amenities, allowing you to unwind in style after a day of exploration. Enjoy the convenience of local fine dining options just a stone's throw away, ensuring every aspect of your stay is both luxurious and memorable. ## Top Winchester Hotel Reviews ![The Farmington Inn & Suites](//images.trvl-media.com/lodging/1000000/20000/10200/10185/1c89931a_y.jpg) ### The Farmington Inn & Suites 10/10 Excellent "Simple, elegant decir and comfortable room. Good access to charging stations, hvac operated as it should, excellent breakfast options—more than continental. Friendly check-in manager. Needs a bit of paint on doors and door woodwork but our 2nd time here and would recommend. " [](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 "Breakfast was really good. They have great espresso machines " [](https://expedia.ca/Hartford-Hotels-Avon-Old-Farms-Hotel.h2635.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) ![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) ![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) ![Americas Best Value Inn Torrington CT](//images.trvl-media.com/lodging/1000000/10000/5800/5738/a9b48332_y.jpg) ### Americas Best Value Inn Torrington CT 10/10 Excellent "The staff was very respectful the room was celan and they were understanding of the circumstance i registered for the rolm under" [](https://expedia.ca/Torrington-Hotels-Americas-Best-Value-Inn-Torrington-CT.h5738.Hotel-Information) ![Days Inn by Wyndham Torrington](//images.trvl-media.com/lodging/1000000/50000/50000/49932/dd052437_y.jpg) ### Days Inn by Wyndham Torrington 10/10 Excellent "Convenient to Warner Theatre and to get back to Rt 4 then Rt 84." [](https://expedia.ca/Torrington-Hotels-Days-Inn-By-Wyndham-Torrington.h49932.Hotel-Information) ## Frequently asked questions ### Are you searching for a great accommodation for your luxury getaway to Winchester? > Use Expedia to arrange your flight to Bradley Intl. Airport (BDL) airport or Westfield, MA (BAF-Barnes Municipal) airport, and then choose from a variety of places to stay that will deliver the luxury you seek. Amenities are an important consideration when you plan a trip, so we make it easy to get what you need to make your stay relaxing and comfortable. If you want a posh hotel with fine dining, a spa, or several swimming pools, Expedia can help you find the best luxury hotel experience that Winchester offers. Winchester has some interesting things to see and do including Highland Lake and Burr Pond State Park, so you might want to take in the local sights during your visit. ### When can I expect good weather in Winchester? > Planning for the weather is an important factor for making your trip to Winchester a success, especially when you're splurging. The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Winchester are January, February, March, and April, with each month seeing an average of 6 inches of snowfall. ### What's there to see and do in Winchester? > Enjoy all that Winchester has to offer and visit Highland Lake, Burr Pond State Park, and Platt Hill State Park. 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