Title: Visit Winchester: Best of Winchester Tourism | Expedia Travel Guide - 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) # Winchester ## Travel Guide ## Visit Winchester Things to do ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=DX_SPRING_PROMO_553248635975869849) - Winchester Hotel Deals - Vacation Rentals in Winchester ![Extended Stay America Suites Hartford Farmington](https://images.trvl-media.com/lodging/1000000/160000/151100/151013/02939ae3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Extended Stay America Suites Hartford Farmington 1 Batterson Park Rd Farmington CT Fully refundableReserve now, pay when you stay CA $103 CA $119 total Feb 24 - Feb 25 includes taxes & fees Book a stay at this business-friendly hotel in Farmington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ... 8/10 Very Good! (1,000 reviews) Everything was good Reviewed on Feb 15, 2026 [](https://expedia.ca/Hotel-Search?startDate=24%2F02%2F2026&endDate=25%2F02%2F2026&selected=151013&PinnedHotelID=151013&HadPinnedHotel=true®ionId=553248635975869849) ![Delamar West Hartford](https://images.trvl-media.com/lodging/19000000/18170000/18166800/18166744/d809cec2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Delamar West Hartford 1 Memorial Road West Hartford CT CA $463 CA $553 total Mar 1 - Mar 2 includes taxes & fees Book a stay at this spa hotel in West Hartford. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ... 9.8/10 Exceptional! (1,000 reviews) Great experience Reviewed on Feb 15, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=18166744&PinnedHotelID=18166744&HadPinnedHotel=true®ionId=553248635975869849) ![Hampton Inn & Suites Hartford/Farmington](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970540/393f3b68_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn & Suites Hartford/Farmington 301 Colt Hwy Farmington CT CA $167 CA $192 total Feb 28 - Mar 1 includes taxes & fees Book a stay at this business-friendly hotel in Farmington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ... 8.8/10 Excellent! (1,000 reviews) they didn’t have a room for me, send me to another hotel that didn’t have the same amenities. i didn’t have to pay for the room, they gave me a full credit, however, they didn’t inform me until i got to the hotel, i should have gotten an email or a call, and i was very unhappy that their was no hot ... Reviewed on Feb 16, 2026 [](https://expedia.ca/Hotel-Search?startDate=28%2F02%2F2026&endDate=01%2F03%2F2026&selected=2970540&PinnedHotelID=2970540&HadPinnedHotel=true®ionId=553248635975869849) [See all 686 properties in Winchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=19%2F02%2F2026&endDate=20%2F02%2F2026®ionId=553248635975869849) 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. ![The Cottage at Highland Lake, year-round, waterfront with a boat dock ](https://images.trvl-media.com/lodging/93000000/92340000/92330500/92330469/973d2b6d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Cottage at Highland Lake, year-round, waterfront with a boat dock Winsted CT Stay at this cottage in Winsted. Enjoy free WiFi, a garden, and patios. Popular attractions The Marina at Highland Lake and Winchester Historical Society are ... 9.6/10 Exceptional! (11 reviews) Very clean and comfortable. Great view! Thank you. Reviewed on Nov 16, 2025 [](https://expedia.ca/Winsted-Hotels-The-Cottage-At-Highland-Lake.h92330469.Hotel-Information) ![Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!](https://images.trvl-media.com/lodging/79000000/78710000/78701100/78701034/be941bed_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut! Great Barrington MA Stay at this vacation home in Great Barrington. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Ski Butternut and Lake Buel are located ... 10/10 Exceptional! (31 reviews) Great house with plenty of bedrooms and space! Perfect location for a ski weekend. Reviewed on Jan 16, 2026 [](https://expedia.ca/Great-Barrington-Hotels-Minutes-From-Ski-Butternut.h78701034.Hotel-Information) ![Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT](https://images.trvl-media.com/lodging/100000000/99810000/99802600/99802538/a214acc6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT Egremont MA Stay at this vacation home in Egremont. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Thom Reed UFO Monument Park and W.E.B. Du Bois ... 9.8/10 Exceptional! (27 reviews) Beautiful house and setting. Everything was just great! Can’t wait to come back. Reviewed on Jan 18, 2026 [](https://expedia.ca/South-Egremont-Hotels-Charming-Idyllic-Farmhouse-Minutes-To-Great-Barrington-MA-And-Salisbury-CT.h99802538.Hotel-Information) [See all properties in Winchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=553248635975869849&sort=VACATION_RENTAL) 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. ## Check Winchester hotel availability [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975869849&startDate=2026-02-18&endDate=2026-02-19)[Feb 18 - Feb 19](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975869849&startDate=2026-02-18&endDate=2026-02-19) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975869849&startDate=2026-02-19&endDate=2026-02-20)[Feb 19 - Feb 20](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975869849&startDate=2026-02-19&endDate=2026-02-20) [This weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975869849&startDate=20%2F02%2F2026&endDate=22%2F02%2F2026)[Feb 20 - Feb 22](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975869849&startDate=20%2F02%2F2026&endDate=22%2F02%2F2026) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975869849&startDate=27%2F02%2F2026&endDate=01%2F03%2F2026)[Feb 27 - Mar 1](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975869849&startDate=27%2F02%2F2026&endDate=01%2F03%2F2026) ### Popular places to visit #### Highland Lake Commune with nature and explore the great outdoors at Highland Lake during your travels in Winchester. [](https://expedia.ca/Highland-Lake-Winsted.d553248635976195024.Vacation-Attraction) #### The Marina at Highland Lake Explore the waterfront in Winchester with a trip to The Marina at Highland Lake. [](https://expedia.ca/The-Marina-At-Highland-Lake-Winsted.d974583590343946240.Vacation-Attraction) #### Ledgebrook Plaza You can enjoy retail therapy at Ledgebrook Plaza during your stay in Winchester. [](https://expedia.ca/Ledgebrook-Plaza-Winsted.d932923715386359808.Vacation-Attraction) #### Platt Hill State Park You can take time to visit Platt Hill State Park during your travels to Winchester. [](https://expedia.ca/Platt-Hill-State-Park-Winsted.d637209897707294720.Vacation-Attraction) #### Northwestern Connecticut Community College Walk around the campus at Northwestern Connecticut Community College as part of your travels around Winchester. [](https://expedia.ca/Northwestern-Connecticut-Community-College-Winsted.d932924108791123968.Vacation-Attraction) #### Winchester Historical Society You can spend an afternoon exploring the galleries in Winchester Historical Society during your trip to Winchester. Take in the live music in this relaxing area. [](https://expedia.ca/Winchester-Historical-Society-Winsted.d553248621532666031.Vacation-Attraction) - Cities near Winchester - Places of interest - [Elizabeth Park ](https://expedia.ca/Elizabeth-Park-Connecticut.d6071397.Vacation-Attraction) - [Macedonia Brook State Park ](https://expedia.ca/Macedonia-Brook-State-Park-Kent.d553248621559724909.Vacation-Attraction) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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