Title: Book the Best Windsor WINERY Hotels in 2026 | Expedia.ca [Hotels in Windsor](https://expedia.ca/Windsor-Hotels.d7881.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.ca/Windsor-Vacation-Rentals.d7881.Travel-Guide-VacationRentals)[Flights to Windsor](https://expedia.ca/Cheap-Flights-To-Windsor.d7881.Travel-Guide-Flights)[Windsor Car Rentals](https://expedia.ca/Car-Rentals-In-Windsor.d7881.Car-Rental-Guide)[Windsor Vacation Packages](https://expedia.ca/Windsor.d7881.Destination-Travel-Guides) ![Cornish Windsor Covered Bridge](https://images.trvl-media.com/place/183560/cb657638-a45b-4260-96ba-18d22ff7fd4b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/183560/cb657638-a45b-4260-96ba-18d22ff7fd4b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 Windsor Winery Hotels Tonight [Mar 23 - Mar 24](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2026-03-23&endDate=2026-03-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 24 - Mar 25](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2026-03-24&endDate=2026-03-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2026-03-27&endDate=2026-03-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2026-04-03&endDate=2026-04-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Windsor hotels with winery ![Exterior](https://images.trvl-media.com/lodging/73000000/72610000/72603600/72603570/w2000h1332x0y1-7eab51dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/73000000/72610000/72603600/72603570/w1999h1332x1y1-792770fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/73000000/72610000/72603600/72603570/dd5b1f55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/73000000/72610000/72603600/72603570/w1997h1332x0y1-5ccae90d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Two Double bed Hotel Room with outdoor heated pool 216 [](https://www.expedia.ca/Bridgewater-Corners-Hotels-Two-Double-Bed-Hotel-Room-With-Outdoor-Heated-Pool-216.h72603570.Hotel-Information) Killington CA $174 CA $256 total includes taxes & fees Mar 24 - Mar 25 [](https://www.expedia.ca/Bridgewater-Corners-Hotels-Two-Double-Bed-Hotel-Room-With-Outdoor-Heated-Pool-216.h72603570.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/39000000/38200000/38197000/38196993/w2000h1332x0y1-debdc5ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/39000000/38200000/38197000/38196993/w1999h1332x1y1-5c4dd77d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/39000000/38200000/38197000/38196993/5f7ca819.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![WiFi](https://images.trvl-media.com/lodging/39000000/38200000/38197000/38196993/w1999h1332x1y1-dd061e19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Two Double Bed Standard Hotel Room with outdoor heated pool 101 [](https://www.expedia.ca/Killington-Hotels-Two-Double-Bed-Standard-Hotel-Room-With-Outdoor-Heated-Pool-101.h38196993.Hotel-Information) Killington 8.2/10 Very good (17 reviews) "Loved this lodging. Super fun outdoorsy place. Enjoyed the warm pool and grills and picnic table area. Liked the coffee in mornings in the office. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dr Arun CA $174 CA $256 total includes taxes & fees Mar 25 - Mar 26 [](https://www.expedia.ca/Killington-Hotels-Two-Double-Bed-Standard-Hotel-Room-With-Outdoor-Heated-Pool-101.h38196993.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/39000000/38320000/38314400/38314377/w2000h1332x0y1-82915084.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![WiFi, bed sheets](https://images.trvl-media.com/lodging/39000000/38320000/38314400/38314377/w1999h1332x1y1-198a7add.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/39000000/38320000/38314400/38314377/w1996h1332x1y1-12511705.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/39000000/38320000/38314400/38314377/w2000h1332x0y1-5869c686.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 107 Deluxe Studio Queen, w/ Sleeper sofa w/ outdoor heated pool [](https://www.expedia.ca/Bridgewater-Corners-Hotels-107-Deluxe-Studio-Queen.h38314377.Hotel-Information) Killington 8.0/10 Very good (7 reviews) "Efficient and affordable option for a short stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marnie O. CA $174 CA $253 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Bridgewater-Corners-Hotels-107-Deluxe-Studio-Queen.h38314377.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/39000000/38830000/38825300/38825273/w2000h1332x0y1-8c82a951.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/39000000/38830000/38825300/38825273/45590506.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38830000/38825300/38825273/w1999h1332x1y1-994c8c65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38830000/38825300/38825273/w1997h1332x0y1-20fc81a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Deluxe One bedroom Queen Suite on the 2nd floor with outdoor heated pool 209 [](https://www.expedia.ca/Killington-Hotels-Deluxe-One-Bedroom-Queen-Suite-On-The-2nd-Floor-With-Outdoor-Heated-Pool-209.h38825273.Hotel-Information) Killington 8.8/10 Excellent (14 reviews) "My fiancé and I needed a quiet fall retreat and this was the perfect place! Situated right in Killington we were super close to restaurants and secluded enough that it felt like our own little fall hideaway. The property was clean and the room was phenomenal for the price with a full kitchen and living area. There is even a heated pool that was so lovely to relax in after our packed day of activities. It was a short drive to Woodstock and the leaves were just hitting peak season during our stay.... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Catherine T. CA $249 CA $358 total includes taxes & fees Mar 24 - Mar 25 [](https://www.expedia.ca/Killington-Hotels-Deluxe-One-Bedroom-Queen-Suite-On-The-2nd-Floor-With-Outdoor-Heated-Pool-209.h38825273.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/56000000/55100000/55094400/55094308/w2000h1332x0y1-4390548f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/56000000/55100000/55094400/55094308/w1997h1332x0y1-e5f5aef2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/56000000/55100000/55094400/55094308/w1996h1332x1y1-4dc7e240.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/56000000/55100000/55094400/55094308/w1999h1332x1y1-e1d800f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Two Double bed Standard Hotel room 218 [](https://www.expedia.ca/Killington-Hotels-Two-Double-Bed-Standard-Hotel-Room-218.h55094308.Hotel-Information) Killington 7.0/10 Good (2 reviews) "The room was nice, clean and comfortable, but there was no coffee maker, no refrigerator, no microwave... we couldn't even make hot water in our room, let alone coffee. There wasn't even any coffee available in the lobby/office area in the morning! We had a restful stay, but if you're a morning coffee drinker, make sure you plan ahead for no coffee availability at all!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Todd CA $174 CA $256 total includes taxes & fees Mar 24 - Mar 25 [](https://www.expedia.ca/Killington-Hotels-Two-Double-Bed-Standard-Hotel-Room-218.h55094308.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413501/w2000h1332x0y1-0a9cdce6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![WiFi, bed sheets](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413501/w1999h1332x1y1-4794ba40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413501/w1999h1332x1y1-4b045cbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413501/1b255611.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Queen Studio on the 2nd floor with outdoor heated pool 207 [](https://www.expedia.ca/Bridgewater-Corners-Hotels-Queen-Studio-On-The-2nd-Floor-With-Outdoor-Heated-Pool-207.h38413501.Hotel-Information) Killington 8.0/10 Very good (6 reviews) "It was fine for our 1 night stay in the area. When I booked I did not realize that this is a motel." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura D. CA $174 CA $253 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Bridgewater-Corners-Hotels-Queen-Studio-On-The-2nd-Floor-With-Outdoor-Heated-Pool-207.h38413501.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/39000000/38200000/38194900/38194814/w1999h1332x1y1-7c3c3328.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/39000000/38200000/38194900/38194814/65c9c72c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38200000/38194900/38194814/w1997h1332x0y1-b5bcbc0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/39000000/38200000/38194900/38194814/w2000h1332x0y1-bab1ded3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 103 Deluxe One bedroom Queen Suite w/ outdoor heated pool [](https://www.expedia.ca/Killington-Hotels-103-Deluxe-One-Bedroom-Queen-Suite-W-Outdoor-Heated-Pool.h38194814.Hotel-Information) Killington 9.6/10 Exceptional (18 reviews) "Would stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hannah M. CA $249 CA $358 total includes taxes & fees Mar 24 - Mar 25 [](https://www.expedia.ca/Killington-Hotels-103-Deluxe-One-Bedroom-Queen-Suite-W-Outdoor-Heated-Pool.h38194814.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/45000000/44450000/44445100/44445040/w2000h1332x0y1-343451ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/45000000/44450000/44445100/44445040/w1996h1332x1y1-dc14c8af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/45000000/44450000/44445100/44445040/w1997h1332x0y1-b2850295.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/45000000/44450000/44445100/44445040/w1999h1332x1y1-90a86e07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Two Double bed Standard Hotel room 219 [](https://www.expedia.ca/Bridgewater-Corners-Hotels-Two-Double-Bed-Standard-Hotel-Room-219.h44445040.Hotel-Information) Killington 7.6/10 Good (4 reviews) "Very clean and easy access." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $174 CA $256 total includes taxes & fees Mar 24 - Mar 25 [](https://www.expedia.ca/Bridgewater-Corners-Hotels-Two-Double-Bed-Standard-Hotel-Room-219.h44445040.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/45000000/44450000/44445200/44445156/w2000h1332x0y1-357770bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/45000000/44450000/44445200/44445156/w1999h1332x1y1-7c92b6d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/45000000/44450000/44445200/44445156/w1997h1332x0y1-3cc2e120.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/45000000/44450000/44445200/44445156/f58cecfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cedarbrook Hotel Room 2 Doubles 119 [](https://www.expedia.ca/Bridgewater-Corners-Hotels-Cedarbrook-Hotel-Room-W2-Doubles-119.h44445156.Hotel-Information) Killington 9.0/10 Wonderful (7 reviews) "The place was an ok place to "crash" after a day of out side activities. The rug needs to be replaced or shampooed. The beds are not very comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leslie CA $174 CA $253 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Bridgewater-Corners-Hotels-Cedarbrook-Hotel-Room-W2-Doubles-119.h44445156.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/39000000/38420000/38412300/38412298/w2000h1332x0y1-ffd96318.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/39000000/38420000/38412300/38412298/6e051916.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38420000/38412300/38412298/w1999h1332x1y1-cf6d1a7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/39000000/38420000/38412300/38412298/w1999h1332x1y1-b3dcc7e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Two Queen Bed Standard Hotel room with outdoor heated pool 201 [](https://www.expedia.ca/Killington-Hotels-Two-Queen-Bed-Standard-Hotel-Room-With-Outdoor-Heated-Pool-201.h38412298.Hotel-Information) Killington 8.6/10 Excellent (14 reviews) "It was a great place for us to spend the night before continuing our travel up north to see the eclipse ☀️ " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lucy Marshall CA $174 CA $256 total includes taxes & fees Mar 24 - Mar 25 [](https://www.expedia.ca/Killington-Hotels-Two-Queen-Bed-Standard-Hotel-Room-With-Outdoor-Heated-Pool-201.h38412298.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=2026-04-06&endDate=2026-04-07®ionId=7881&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Windsor Hotel Reviews ![On The River Inn](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/8d6bfa64_y.jpg) ### On The River Inn 10/10 Excellent "What a Jem! Loved it here:-) " [](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [Beach Hotel Hotels in Ascutney ](https://www.expedia.ca/Ascutney-Hotels-Beach-Hotel.0-0-d6046953-tBeachHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Ascutney ](https://www.expedia.ca/Ascutney-Hotels-Luxury-Hotel.0-0-d6046953-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Mountain Hotels in Ascutney ](https://www.expedia.ca/Ascutney-Hotels-Mountain-Hotels.0-0-d6046953-tMountainHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Ascutney ](https://www.expedia.ca/Ascutney-Hotels-Pet-Friendly-Hotel.0-0-d6046953-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Ascutney ](https://www.expedia.ca/Ascutney-Hotels-Romantic-Hotel.0-0-d6046953-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Ski Hotels in Ascutney ](https://www.expedia.ca/Ascutney-Hotels-Ski-Hotel.0-0-d6046953-tSkiHotel.Travel-Guide-Filter-Hotels) - 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