Title: Winchester Vacation Home Rentals from CA $120: Search Top Private Vacation Homes for Rent | 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) # Winchester Vacation Rentals ![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 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-10-10&endDate=2025-10-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-10-17&endDate=2025-10-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-10-31&endDate=2025-11-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-11-28&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winchester Vacation Homes ![Fireplace](https://images.trvl-media.com/lodging/109000000/108940000/108933900/108933820/9134b65e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/109000000/108940000/108933900/108933820/e9148cd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/109000000/108940000/108933900/108933820/6e496195.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108940000/108933900/108933820/w1024h824x0y0-e0ef6851.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Room/Sunny/Clean/Peace/SelfCheckIn Harwinton 10/10 Exceptional (1) "We enjoyed our stay, would definitely highly recommend " CA $201 CA $260 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Harwinton-Hotels-Private-RoomSunnyCleanPeaceSelfCheckIn.h108933820.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/3db87cef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/e729bc4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/1c3ab355.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/31d52781.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### CT Gate House Goshen CT, Gate House Goshen CT Goshen 10/10 Exceptional (6) "Wonderful stay. It really is a gate house. The property is beautiful and the house is spacious. If I was eloquent,I could go on and on... " CA $140 CA $887 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Goshen-Hotels-Gate-House-Goshen-CT.h106031055.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/108000000/107970000/107960200/107960143/81d94858.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107970000/107960200/107960143/3113c54f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107970000/107960200/107960143/658a02cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107970000/107960200/107960143/1abd1fb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sun Filled Lake House Living Avon 8.0/10 Very good (2) "Enjoyed my stayConvenient location for restaurants, shopping etcHome was clean and neat and in a nice quiet neighborhood Good value" CA $118 CA $399 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Avon-Hotels-Sun-Filled-Lake-House-Living.h107960143.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/109000000/108200000/108190300/108190201/ce4ac8e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/109000000/108200000/108190300/108190201/8311b1e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108200000/108190300/108190201/104bd215.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108200000/108190300/108190201/90ae7f9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Family Retreat | Near Downtown Hartford | Sleeps 10 Bloomfield 9.4/10 Exceptional (3) "There were 7 of us staying for a Wedding near by. The home was bright, clean and very roomy. I would 100% stay here again. Host was on top of everything!! " CA $246 CA $747 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Bloomfield-Hotels-Modern-Family-Retreat-Near-Downtown-Hartford-Sleeps-10.h108190201.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/111000000/110380000/110372000/110371901/a160af85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/110380000/110372000/110371901/7686f6ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/111000000/110380000/110372000/110371901/99bd2597.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/111000000/110380000/110372000/110371901/3c2e92b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Sun Filled Cozy Creamery Plainville 8.8/10 Excellent (21) "Nice,cozy and a reasonable rate." CA $116 CA $374 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Plainville-Hotels-The-Sun-Filled-Cozy-Creamery.h110371901.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102410000/102404400/102404341/c01826e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102410000/102404400/102404341/9035e4d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/103000000/102410000/102404400/102404341/0d33755f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/103000000/102410000/102404400/102404341/d458bfe7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford Bloomfield 9.2/10 Wonderful (7) "Beautiful new spacious property in a great safe neighborhood. Very nice for groups. Common Living space s conducive for gathering. Property still under construction as there were other homes still being built. Near busy street but monimal noise. Would stay again." CA $221 CA $760 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Bloomfield-Hotels-Massive-5-Bedrooms-3King-2Queen.h102404341.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/115000000/114880000/114878300/114878238/abcd3f54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114880000/114878300/114878238/w5278h3491x0y0-d48a63f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/115000000/114880000/114878300/114878238/e6df39fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114880000/114878300/114878238/5ffcffb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home in the Woods Russell 10/10 Exceptional (3) "Jessica's spot is adorable and tidy, at the end of a quiet, shady lane, with lots of peace and privacy. It was a hot, muggy weekend but there were 2 window units and extra fans to keep us comfortable. The house is well-appointed—we had a busy schedule and were sad we didn't have a chance to use the lovely outdoor fire pit area. Good communication after a minor mixup. Would definitely stay again!" CA $236 CA $448 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Westfield-Hotels-Home-In-The-Woods.h114878238.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113210000/113200800/113200740/045435f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, stereo](https://images.trvl-media.com/lodging/114000000/113210000/113200800/113200740/8a868c6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113210000/113200800/113200740/058c7fd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113210000/113200800/113200740/0ed108d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do East Granby 10/10 Exceptional (2) "Great Stay at the Olde Tobacco Barn. Was here for a work trip, and the place was perfect for our needs. House is set back really nicely and private. Host was super responsive and easy to deal with. Overall 5/5 stay. Thank you!" CA $379 CA $698 total includes taxes & fees Oct 10 - Oct 11 [](https://www.expedia.ca/East-Granby-Hotels-The-Olde-Tobacco-Barn-East-Granby-Close-To-Airport.h113200740.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118710000/118704500/118704493/7540cd23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/119000000/118710000/118704500/118704493/81649787.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/119000000/118710000/118704500/118704493/2ac2f793.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118710000/118704500/118704493/3efd2236.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### KING BED, Affordable Classic Bristol Home Sleep 8+ Bristol CA $135 CA $364 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Bristol-Hotels-KING-BED.h118704493.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/112000000/111930000/111926200/111926107/af154576.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Eco-friendly toiletries, hair dryer](https://images.trvl-media.com/lodging/112000000/111930000/111926200/111926107/d6057517.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111930000/111926200/111926107/368587af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/112000000/111930000/111926200/111926107/c4566b37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Jefferson Guest House, Spacious, Special Views Litchfield 10/10 Exceptional (7) "I stayed here for four nights, including one with my son, and it was fantastic.Everything is brand new, clean, and beautifully appointed, with every amenity you could want." CA $349 CA $459 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Litchfield-Hotels-The-Jefferson-House.h111926107.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96930000/96925100/96925078/a263f049.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96930000/96925100/96925078/adb1247d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/97000000/96930000/96925100/96925078/22f0c0fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96930000/96925100/96925078/b3e2f129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tranquil Litchfield Connecticut Retreat". Litchfield 9.4/10 Exceptional (17) "Good communication from the host" CA $314 CA $449 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Tranquil-Litchfield-Connecticut-Retreat.h96925078.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/119000000/118470000/118467400/118467341/cb8efd3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/119000000/118470000/118467400/118467341/d975f5d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118470000/118467400/118467341/0bc1df65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/119000000/118470000/118467400/118467341/ac949794.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Whispering Estate Guest House - A Romantic Countryside Getaway Goshen 10/10 Exceptional (3) "Beautiful property and great location. A true retreat. " CA $1,117 CA $1,694 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Goshen-Hotels-Charming-Retreat-At-Stone-Hill-Estate-Nature-Meets-Luxury.h118467341.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/7377fc19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/508c5b2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/0e82b119.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/f63afa55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Big farmhouse in the foothills of the Berkshires Russell 10/10 Exceptional (140) "Lovely old farmhouse with authentic yet comfortable furnishings. Would recommend!" CA $279 CA $498 total includes taxes & fees Oct 24 - Oct 25 [](https://www.expedia.ca/Russell-Hotels-Big-Farmhouse-In-The-Foothills-Of-The-Berkshires.h19107245.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/665b8282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/99d3f85f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/8f9296e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/f26544ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cheerful 3-bedroom cottage with woodstove Sheffield 10/10 Exceptional (39) "The property was centrally located for skiing, and was a comfortable stay." CA $331 CA $702 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Sheffield-Hotels-Cheerful-3-Bedroom-Cottage-With-Woodstove.h75599864.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96980000/96978000/96977909/07ae7a36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96980000/96978000/96977909/7a49e3f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/97000000/96980000/96978000/96977909/5bf6f7a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96980000/96978000/96977909/080b7469.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 3-bedroom Modern cottage with lakeside views Hartland CA $1,257 CA $2,076 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/East-Hartland-Hotels-Charming-3-Bedroom-House-In-Pleasant-Hartland.h96977909.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/52000000/51690000/51685500/51685419/1bc1a012.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/52000000/51690000/51685500/51685419/cd7d0c00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/52000000/51690000/51685500/51685419/w1026h680x0y3-1207c37a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/52000000/51690000/51685500/51685419/010bda9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville Collinsville 10/10 Exceptional (61) "There is a lot of fun things to do close by. The house was spotless and it was nice to relax on the sofa or outside patio and look at the river. " CA $403 CA $674 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Canton-Hotels-Gorgeous-River-Views-On-Rails-To-Trails-And-Just-Steps-To-Quaint-Collinsville.h51685419.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120480000/120478900/120478833/5e06d78f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120480000/120478900/120478833/07a4e6da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120480000/120478900/120478833/52994ebd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120480000/120478900/120478833/f3c03178.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family-Friendly Retreat - Sleeps 20 in Bloomfield, CT Bloomfield CA $630 CA $1,717 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Bloomfield-Hotels-Family-Friendly-Retreat-Sleeps-20-In-Bloomfield.h120478833.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/109000000/108190000/108188500/108188444/f02ef755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/109000000/108190000/108188500/108188444/a8bdd677.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108190000/108188500/108188444/3af0801b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108190000/108188500/108188444/7a78b0cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stylish Townhome | Perfect for Family Gatherings & Events Bloomfield 10/10 Exceptional (4) "The house was newer and the living room and kitchen had open layout that enabled to spend quality time with family." CA $246 CA $750 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Bloomfield-Hotels-Stylish-Townhome-Perfect-For-Family-Gatherings-Events.h108188444.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=2025-10-17&endDate=2025-10-18®ionId=553248635975869849&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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-Private-Vacation-Homes.d553248635975869849-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Private-Vacation-Homes.d553248635975869849-aaPrivateVacationHomes.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 "The staff was welcoming and friendly. The clerk noticed that I had booked a handicap room, which I was unaware of, and upgraded me to a regular room without a problem. This location is excellent as it is right off the interstate, and easy access to shops nearby." [](https://expedia.ca/Hartford-Hotels-Extended-Stay-America-Suites-Hartford-Farmington.h151013.Hotel-Information) ![Homewood Suites by Hilton Hartford-Farmington](//images.trvl-media.com/lodging/1000000/210000/203500/203496/4f26a2b3_y.jpg) ### Homewood Suites by Hilton Hartford-Farmington 10/10 Excellent "Safe secure, parking area, staff was very polite and friendly, breakfast was complete with everything you would want." [](https://expedia.ca/Hartford-Hotels-Homewood-Suites-By-Hilton-Hartford-Farmington.h203496.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 "Great! " [](https://expedia.ca/Hartford-Hotels-The-Farmington-Inn-Suites.h10185.Hotel-Information) ![Fairfield Inn & Suites by Marriott Plainville](//images.trvl-media.com/lodging/1000000/10000/10000/9965/01d5897d_y.jpg) ### Fairfield Inn & Suites by Marriott Plainville 10/10 Excellent "Wonderful stay except the pool was out of order and no hot tub or steam room" [](https://expedia.ca/Hartford-Hotels-Fairfield-Inn-Suites-By-Marriott-Plainville.h9965.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 "Convenient " [](https://expedia.ca/Hartford-Hotels-Sheraton-Hartford-Hotel-At-Bradley-Airport.h4632.Hotel-Information) ![Simsbury 1820 House](//images.trvl-media.com/lodging/1000000/50000/42300/42279/6326a611_y.jpg) ### Simsbury 1820 House 10/10 Excellent "Very nice. " [](https://expedia.ca/Hartford-Hotels-Simsbury-1820-House.h42279.Hotel-Information) ![Hampton Inn & Suites Hartford/Farmington](//images.trvl-media.com/lodging/3000000/2980000/2970600/2970540/393f3b68_y.jpg) ### Hampton Inn & Suites Hartford/Farmington 10/10 Excellent "Nicely appointed room - mini suite. Dog friendly. Comfy and clean" [](https://expedia.ca/Hartford-Hotels-Hampton-Inn-And-Suites-HartfordFarmington.h2970540.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) ![Delamar West Hartford](//images.trvl-media.com/lodging/19000000/18170000/18166800/18166744/d809cec2_y.jpg) ### Delamar West Hartford 10/10 Excellent "Spa" [](https://expedia.ca/Hartford-Hotels-Delamar-West-Hartford.h18166744.Hotel-Information) ## Find out more about Winchester ## Winchester Vacation Homes information | Number of reviews | 12,458 | | --- | --- | | Accommodation | 227 Vacation Homes | | Lowest Price | CA $120 | | Highest Price | CA $519 | ## Explore a world of travel with Expedia - 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