Title: Windsor Guest Houses from CA $368 | Expedia.ca [Hotels in Windsor](https://expedia.ca/Windsor-Hotels.d7880.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.ca/Windsor-Vacation-Rentals.d7880.Travel-Guide-VacationRentals)[Flights to Windsor](https://expedia.ca/Cheap-Flights-To-Windsor.d7880.Travel-Guide-Flights)[Windsor Car Rentals](https://expedia.ca/Car-Rentals-In-Windsor.d7880.Car-Rental-Guide)[Windsor Vacation Packages](https://expedia.ca/Windsor.d7880.Destination-Travel-Guides) ![Old tobacco barn with oak trees](https://images.trvl-media.com/place/7880/7cec51be-160c-4c0b-93cb-c61bca24b629.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Guest Houses in Windsor from CA $368 - ![](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 Next weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=7880&startDate=2026-01-09&endDate=2026-01-11&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=7880&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=7880&startDate=2026-01-30&endDate=2026-02-01&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=7880&startDate=2026-02-27&endDate=2026-03-01&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Windsor guest houses ![Exterior detail](https://images.trvl-media.com/lodging/20000000/19820000/19812300/19812250/beddc5d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/20000000/19820000/19812300/19812250/9e5b89dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/20000000/19820000/19812300/19812250/ab7a0a06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/20000000/19820000/19812300/19812250/bee8460a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A European Country Getaway \~ 1930s Stone Cottage In Connecticut! [](https://www.expedia.ca/North-Granby-Hotels-A-European-Country-Getaway-1930s-Stone-Cottage-In-Connecticut.h19812250.Hotel-Information) Granby 10/10 Exceptional (95) "This was an incredibly beautiful place to spend a restful weekend. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Meagan M. CA $206 CA $368 total includes taxes & fees Jan 4 - Jan 5 [](https://www.expedia.ca/North-Granby-Hotels-A-European-Country-Getaway-1930s-Stone-Cottage-In-Connecticut.h19812250.Hotel-Information) ![Flat-screen TV, fireplace](https://images.trvl-media.com/lodging/33000000/32610000/32607500/32607433/d767700d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort House, 4 Bedrooms, Non Smoking](https://images.trvl-media.com/lodging/33000000/32610000/32607500/32607433/2c7a0a55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort House, 4 Bedrooms, Non Smoking | In-room dining](https://images.trvl-media.com/lodging/33000000/32610000/32607500/32607433/5589f12e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV, fireplace](https://images.trvl-media.com/lodging/33000000/32610000/32607500/32607433/a63f9c0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Upscaled Home in a Quiet Neighborhood [](https://www.expedia.ca/Springfield-Hotels-Upscaled-Home-In-A-Quiet-Neighborhood.h32607433.Hotel-Information) Forest Park 8.4/10 Very good (5) "So clean and comfy" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $376 CA $606 total includes taxes & fees Jan 10 - Jan 11 [](https://www.expedia.ca/Springfield-Hotels-Upscaled-Home-In-A-Quiet-Neighborhood.h32607433.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=2026-01-17&endDate=2026-01-18®ionId=7880&adults=2&lodging=GUEST_HOUSE&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%2FWindsor-Guest-Houses.d7880-aaGuestHouses.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindsor-Guest-Houses.d7880-aaGuestHouses.Travel-Guide-Accommodation) ## Top Windsor Hotel Reviews ![Holiday Inn Express Southington by IHG](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/120068a2_y.jpg) ### Holiday Inn Express Southington by IHG 10/10 Excellent "Clean comfortable room, friendly staff, great breakfast" [](https://expedia.ca/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.Hotel-Information) ![Extended Stay America Suites Hartford Farmington](https://images.trvl-media.com/lodging/1000000/160000/151100/151013/02939ae3_y.jpg) ### Extended Stay America Suites Hartford Farmington 10/10 Excellent "Great place." [](https://expedia.ca/Hartford-Hotels-Extended-Stay-America-Suites-Hartford-Farmington.h151013.Hotel-Information) ![Days Inn by Wyndham Windsor Locks / Bradley Intl Airport](https://images.trvl-media.com/lodging/1000000/20000/17600/17518/1117a9b1_y.jpg) ### Days Inn by Wyndham Windsor Locks / Bradley Intl Airport 10/10 Excellent "Air conditioning effectively nice breakfast all on point also nice staff 👌 " [](https://expedia.ca/Hartford-Hotels-Days-Inn-By-Wyndham-Windsor-Locks-Bradley-Intl-Airport.h17518.Hotel-Information) ![HYATT house Hartford North/Windsor](https://images.trvl-media.com/lodging/3000000/2230000/2220600/2220580/5ad64187_y.jpg) ### HYATT house Hartford North/Windsor 10/10 Excellent "Staff was top tier " [](https://expedia.ca/Hartford-Hotels-HYATT-House-Hartford-NorthWindsor.h2220580.Hotel-Information) ![MGM Springfield](https://images.trvl-media.com/lodging/28000000/27670000/27664900/27664860/c76c1f43_y.jpg) ### MGM Springfield 10/10 Excellent "Great, clean, spacious, stylish, and good dining." [](https://expedia.ca/Springfield-Hotels-MGM-Springfield.h27664860.Hotel-Information) ![Sheraton Hartford Hotel at Bradley Airport](https://images.trvl-media.com/lodging/1000000/10000/4700/4632/c8edc11d_y.jpg) ### Sheraton Hartford Hotel at Bradley Airport 10/10 Excellent "Large clean room" [](https://expedia.ca/Hartford-Hotels-Sheraton-Hartford-Hotel-At-Bradley-Airport.h4632.Hotel-Information) ![Hampton Inn Hartford/Airport](https://images.trvl-media.com/lodging/1000000/900000/892600/892590/4a4de62f_y.jpg) ### Hampton Inn Hartford/Airport 10/10 Excellent "Second time here, breakfast was always fresh, pool was clean and staff was friendly. My son and I loved the hot chocolate bar with the coffee and tea all day. It was such a nice touch visiting around the holidays " [](https://expedia.ca/Hartford-Hotels-Hampton-Inn-HartfordAirport.h892590.Hotel-Information) ![Candlewood Suites Windsor Locks Bradley Arpt by IHG](https://images.trvl-media.com/lodging/2000000/1620000/1619200/1619197/f7719b06_y.jpg) ### Candlewood Suites Windsor Locks Bradley Arpt by IHG 10/10 Excellent "Helpful friendly staff, clean room with very nice amenities." [](https://expedia.ca/Hartford-Hotels-Candlewood-Suites-Windsor-Locks-Bradley-Arpt.h1619197.Hotel-Information) ![Hampton Inn & Suites Hartford/East Hartford](https://images.trvl-media.com/lodging/3000000/2950000/2943100/2943093/5cf369a5_y.jpg) ### Hampton Inn & Suites Hartford/East Hartford 10/10 Excellent "Great experience and staff" [](https://expedia.ca/Hartford-Hotels-Hampton-Inn-Suites-HartfordEast-Hartford.h2943093.Hotel-Information) ## Find out more about Windsor ## Windsor Guest Houses information | Number of reviews | 95 | | ----------------- | -------------- | | Accommodation | 7 Guest Houses | | Lowest Price | CA $368 | | Highest Price | CA $606 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [Farmstay in Bloomfield ](https://www.expedia.ca/Bloomfield-Agritourism.d180160-aaAgritourism.Travel-Guide-Accommodation) - [B&B in Bloomfield ](https://www.expedia.ca/Bloomfield-Bed-And-Breakfast.d180160-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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