Title: Winchester Vacation Home Rentals from CA $336: 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 ![](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 prices for these dates 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=VACATION_HOME&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=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2026-01-30&endDate=2026-02-01&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winchester Vacation Homes ![Interior](https://images.trvl-media.com/lodging/109000000/108200000/108190300/108190201/ce4ac8e2.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) ![Property grounds](https://images.trvl-media.com/lodging/109000000/108200000/108190300/108190201/8311b1e1.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 $749 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Bloomfield-Hotels-Modern-Family-Retreat-Near-Downtown-Hartford-Sleeps-10.h108190201.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/1e32801e.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 $892 total includes taxes & fees Oct 12 - Oct 13 [](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) ![Interior](https://images.trvl-media.com/lodging/108000000/107970000/107960200/107960143/658a02cd.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/108000000/107970000/107960200/107960143/1abd1fb9.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 $144 CA $430 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Avon-Hotels-Sun-Filled-Lake-House-Living.h107960143.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110380000/110372000/110371901/0f29f441.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 (22) "Nice,cozy and a reasonable rate." CA $116 CA $378 total includes taxes & fees Oct 18 - Oct 19 [](https://www.expedia.ca/Plainville-Hotels-The-Sun-Filled-Cozy-Creamery.h110371901.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118710000/118704500/118704493/245a5e30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118710000/118704500/118704493/f8ea175c.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/b51643ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118710000/118704500/118704493/258e217a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### KING BED, Affordable Classic Bristol Home Sleep 8+ Bristol CA $110 CA $336 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Bristol-Hotels-KING-BED.h118704493.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29640000/29631700/29631677/21fd7b1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, music library](https://images.trvl-media.com/lodging/30000000/29640000/29631700/29631677/b8f260da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/30000000/29640000/29631700/29631677/w1409h929x0y11-871fbc5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29640000/29631700/29631677/d3cf9fb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Linny's Lakeview Cottage - Cozy, fun & updated Southwick 10/10 Exceptional (63) "Very great location, close to my family. Great spot!!" CA $209 CA $456 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Springfield-Hotels-Fully-Renovated-Lakeview-Cottage.h29631677.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) ![5 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/103000000/102410000/102404400/102404341/d56e1ed3.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) ![Smart TV](https://images.trvl-media.com/lodging/103000000/102410000/102404400/102404341/0d33755f.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 $359 CA $955 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Bloomfield-Hotels-Massive-5-Bedrooms-3King-2Queen.h102404341.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84090000/84085200/84085164/db0bd685.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/85000000/84090000/84085200/84085164/6ae40622.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/85000000/84090000/84085200/84085164/w1079h703x0y5-19e2087c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, printers](https://images.trvl-media.com/lodging/85000000/84090000/84085200/84085164/7e9dd7f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fave Cape Cod Style Home Retreat: with Main-Level Bedroom bordering Farmington New Britain 10/10 Exceptional (4) "We enjoyed our trip and the house was perfect for us, 3 boys and their father. " [](https://www.expedia.ca/New-Britain-Hotels-Fave-Cape-Cod-Style-Home-Retreat-With-Main-Level-Bedroom-Bordering-Farmington.h84085164.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) ![Exterior](https://images.trvl-media.com/lodging/114000000/113210000/113200800/113200740/058c7fd2.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) ![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 $688 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) ![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) ![Smart TV, fireplace, books, computer monitors](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/af920cc8.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 $690 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Sheffield-Hotels-Cheerful-3-Bedroom-Cottage-With-Woodstove.h75599864.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) ![Exterior](https://images.trvl-media.com/lodging/121000000/120480000/120478900/120478833/f3c03178.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/121000000/120480000/120478900/120478833/859e7aab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family-Friendly Retreat - Sleeps 20 in Bloomfield, CT Bloomfield CA $506 CA $1,538 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Bloomfield-Hotels-Family-Friendly-Retreat-Sleeps-20-In-Bloomfield.h120478833.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) ![Interior](https://images.trvl-media.com/lodging/112000000/111930000/111926200/111926107/368587af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111930000/111926200/111926107/1548a60b.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 $377 CA $491 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Litchfield-Hotels-The-Jefferson-House.h111926107.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) ![Exterior](https://images.trvl-media.com/lodging/97000000/96980000/96978000/96977909/2b36fd43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 3-bedroom Modern cottage with lakeside views Hartland CA $1,256 CA $2,074 total includes taxes & fees Oct 11 - Oct 12 [](https://www.expedia.ca/East-Hartland-Hotels-Charming-3-Bedroom-House-In-Pleasant-Hartland.h96977909.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) ![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/d975f5d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118470000/118467400/118467341/3a77d3b6.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 $1,116 CA $1,693 total includes taxes & fees Oct 10 - Oct 11 [](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) ![Interior](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/af5c0679.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) ### 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 $500 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Russell-Hotels-Big-Farmhouse-In-The-Foothills-Of-The-Berkshires.h19107245.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) ![Dining](https://images.trvl-media.com/lodging/52000000/51690000/51685500/51685419/4f70f9c0.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) ![Exterior](https://images.trvl-media.com/lodging/52000000/51690000/51685500/51685419/cd7d0c00.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 $363 CA $624 total includes taxes & fees Oct 13 - Oct 14 [](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/109000000/108200000/108190400/108190337/57354543.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108200000/108190400/108190337/54bd1291.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/109000000/108200000/108190400/108190337/0a476351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/109000000/108200000/108190400/108190337/10edcc41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Premium 3-Story Townhome | Perfect for Large Groups Bloomfield 9.2/10 Wonderful (5) "Property as advertised & convenient - nice location. Great communication; appreciate the hospitality! " CA $246 CA $749 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Bloomfield-Hotels-Premium-3-Story-Townhome-Perfect-For-Large-Groups.h108190337.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) ![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) ![Interior](https://images.trvl-media.com/lodging/109000000/108190000/108188500/108188444/76ed01a5.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 $399 CA $962 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Bloomfield-Hotels-Stylish-Townhome-Perfect-For-Family-Gatherings-Events.h108188444.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/121000000/120480000/120475300/120475291/a4ce4257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120480000/120475300/120475291/51b25708.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120480000/120475300/120475291/81a2cc78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/121000000/120480000/120475300/120475291/beae8c5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Group-Friendly Townhouse Stay – Sleeps up to 20 Bloomfield CA $850 CA $2,000 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Bloomfield-Hotels-Group-Friendly-Townhouse-Stay-Sleeps-Up-To-20.h120475291.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=2025-10-23&endDate=2025-10-24®ionId=553248635975869849&adults=2&lodging=VACATION_HOME&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-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 "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 Vacation Homes information | Number of reviews | 337 | | --- | --- | | Accommodation | 227 Vacation Homes | | Lowest Price | CA $336 | | Highest Price | CA $2,074 | ## 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) - 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