Title: Book the Best HISTORIC Hotels in Windsor 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 Historic Hotels Tonight [Mar 28 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2026-03-28&endDate=2026-03-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 29 - Mar 30](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2026-03-29&endDate=2026-03-30&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) In two weeks [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2026-04-10&endDate=2026-04-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Windsor historic hotels ![Breakfast, lunch, dinner served; local cuisine ](https://images.trvl-media.com/lodging/4000000/3980000/3974400/3974306/1703a489.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/4000000/3980000/3974400/3974306/d1b03732.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/4000000/3980000/3974400/3974306/724d4250.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/4000000/3980000/3974400/3974306/bf81da74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hanover Inn Dartmouth [](https://www.expedia.ca/Lebanon-Hotels-Hanover-Inn-Dartmouth.h3974306.Hotel-Information) Hanover 9.6/10 Exceptional (928 reviews) "Perfect stay: best service, location, and ambiance!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elena CA $305 CA $330 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Lebanon-Hotels-Hanover-Inn-Dartmouth.h3974306.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/28000000/27120000/27117200/27117112/62670e78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/28000000/27120000/27117200/27117112/c5d0a9bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27120000/27117200/27117112/306e8880.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/28000000/27120000/27117200/27117112/becbfa0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Fully Renovated One-Room Schoolhouse on 22+ acres [](https://www.expedia.ca/Grafton-Hotels-Charming-Fully-Renovated-One-Room-Schoolhouse-On-22-Acres.h27117112.Hotel-Information) Grafton 9.6/10 Exceptional (168 reviews) "Very nice and clean cabin, not too far from small towns, decently supplied for expected conveniences, charming area - a small stream nearby provides a pleasant background noise. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Philip CA $235 CA $509 total includes taxes & fees Apr 1 - Apr 2 [](https://www.expedia.ca/Grafton-Hotels-Charming-Fully-Renovated-One-Room-Schoolhouse-On-22-Acres.h27117112.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1410000/1407200/1407156/c098bcf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo Hotel Room](https://images.trvl-media.com/lodging/2000000/1410000/1407200/1407156/1d8473ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1410000/1407200/1407156/754a77bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Queen Bed](https://images.trvl-media.com/lodging/2000000/1410000/1407200/1407156/41e84082.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castle Hill Resort And Spa [](https://www.expedia.ca/Cavendish-Hotels-Castle-Hill-Resort-And-Spa.h1407156.Hotel-Information) Cavendish 9.0/10 Wonderful (113 reviews) "nice place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) armin CA $238 CA $260 total includes taxes & fees Mar 30 - Mar 31 [](https://www.expedia.ca/Cavendish-Hotels-Castle-Hill-Resort-And-Spa.h1407156.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22870000/22865900/22865847/fe1abb51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22870000/22865900/22865847/344617b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/23000000/22870000/22865900/22865847/1516e7fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/23000000/22870000/22865900/22865847/ad47e382.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle [](https://www.expedia.ca/Ludlow-Hotels-Short-Walk-To-Shops.h22865847.Hotel-Information) Ludlow 9.8/10 Exceptional (108 reviews) "We enjoyed our stay, the house was lovely and close to everything in Ludlow and Okemo." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hannah M. CA $308 CA $617 total includes taxes & fees Mar 30 - Mar 31 [](https://www.expedia.ca/Ludlow-Hotels-Short-Walk-To-Shops.h22865847.Hotel-Information) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/46000000/45710000/45709000/45708952/b0da744f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/46000000/45710000/45709000/45708952/1662100f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/46000000/45710000/45709000/45708952/cb6b5625.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/46000000/45710000/45709000/45708952/37889f48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route [](https://www.expedia.ca/Central-Vermont-Killington-Hotels-Vrbo-Property.h45708952.Hotel-Information) Ludlow 9.8/10 Exceptional (107 reviews) "Great Condo. We had plenty of space. Wendi was very responsive and even accommodated us checking in an hour early when we arrived in town. We would definitely come back. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara M. CA $195 CA $404 total includes taxes & fees Apr 20 - Apr 21 [](https://www.expedia.ca/Central-Vermont-Killington-Hotels-Vrbo-Property.h45708952.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131894/455aec2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131894/2828ea80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131894/146a8911.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131894/77b10ad2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ski-In/Out condo with patio, mountain views, washer/dryer, & cable [](https://www.expedia.ca/Ludlow-Hotels-Ski-InOut-Condo-With-Patio.h72131894.Hotel-Information) Clock Tower Base Area 9.2/10 Wonderful (30 reviews) "Great property, clean and close to the slope" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) tiliger01 CA $78 CA $323 total includes taxes & fees Apr 8 - Apr 9 [](https://www.expedia.ca/Ludlow-Hotels-Ski-InOut-Condo-With-Patio.h72131894.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/73000000/72140000/72131700/72131664/a283578c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/73000000/72140000/72131700/72131664/5c70d1ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/73000000/72140000/72131700/72131664/1dab8185.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72140000/72131700/72131664/98ad84cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck [](https://www.expedia.ca/Plymouth-Hotels-Hawk-Mountain-Retreat-Near-Okemo-With-Fireplace.h72131664.Hotel-Information) Plymouth 9.8/10 Exceptional (24 reviews) "The Nest at Hawk Ledges was a perfect summer getaway. The home provides comfort in a tranquil setting while being close enough to many summer adventures. We enjoyed relaxing in the bright, open home after taking many day trips to explore the area. What a gem!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ben N. CA $270 CA $985 total includes taxes & fees Apr 16 - Apr 17 [](https://www.expedia.ca/Plymouth-Hotels-Hawk-Mountain-Retreat-Near-Okemo-With-Fireplace.h72131664.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) ![Pool](https://images.trvl-media.com/lodging/39000000/38320000/38314400/38314377/w2000h1332x0y1-5869c686.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/39000000/38320000/38314400/38314377/w1996h1332x1y1-71f4d760.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 $175 CA $258 total includes taxes & fees Mar 30 - Mar 31 [](https://www.expedia.ca/Bridgewater-Corners-Hotels-107-Deluxe-Studio-Queen.h38314377.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/w1997h1332x0y1-df9edd8e.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) ### 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 $175 CA $258 total includes taxes & fees Mar 30 - Mar 31 [](https://www.expedia.ca/Bridgewater-Corners-Hotels-Queen-Studio-On-The-2nd-Floor-With-Outdoor-Heated-Pool-207.h38413501.Hotel-Information) ![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) ![Interior](https://images.trvl-media.com/lodging/73000000/72610000/72603600/72603570/w1997h1332x0y1-5ccae90d.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/73000000/72610000/72603600/72603570/w1996h1332x1y1-302f86ad.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 $175 CA $258 total includes taxes & fees Mar 30 - Mar 31 [](https://www.expedia.ca/Bridgewater-Corners-Hotels-Two-Double-Bed-Hotel-Room-With-Outdoor-Heated-Pool-216.h72603570.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=2026-04-11&endDate=2026-04-12®ionId=7881&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Windsor Hotel Reviews ![Pointe at Castle Hill Resort](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/b9b1ed95_y.jpg) ### Pointe at Castle Hill Resort 10/10 Excellent "There's a cute little town nearby with a great coffee shop. " [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![Best Western West Lebanon-Hanover Hotel](https://images.trvl-media.com/lodging/2000000/1210000/1200500/1200405/911e9465_y.jpg) ### Best Western West Lebanon-Hanover Hotel 4/10 Poor "I’ve stayed in budget hotels before, but this was on another level entirely. The room clearly hadn’t been properly cleaned in a long time. The floor was full of crumbs, and there was literally a pile of Cheerios sitting under the door to the connecting room. That alone should have been a red flag. It didn’t get better from there. The shower mat looked like something had chewed a hole straight through it. honestly, it looked like a mouse had been at it. Not exactly what you want to see in a place you’re supposed to relax. The sheets were just as bad; old, rough, and so worn they felt like you were sleeping on sandpaper. To top it all off, I got an automated text at 6:01 a.m. asking how my stay was. Who sends that kind of message that early? If anything, it just highlighted how out of touch the place is with basic guest experience. The only positive is the location—it’s convenient. But that’s not nearly enough to make up for everything else. I wouldn’t stay here again under any circumstances. " [](https://expedia.ca/Lebanon-Hotels-Best-Western-West-Lebanon-Hanover-Hotel.h1200405.Hotel-Information) ![On The River Inn](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/8d6bfa64_y.jpg) ### On The River Inn 10/10 Excellent " Very cozy. Lovely breakfast. Fun smores" [](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ![Align Inn Vermont](https://images.trvl-media.com/lodging/1000000/10000/1200/1108/4cc53d97_y.jpg) ### Align Inn Vermont 8/10 Good "Clean room, friendly staff" [](https://expedia.ca/Quechee-Hotels-Quality-Inn-At-Quechee-Gorge.h1108.Hotel-Information) ![Holiday Inn Club Vacations Mount Ascutney Resort by IHG](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/06298210_y.jpg) ### Holiday Inn Club Vacations Mount Ascutney Resort by IHG 10/10 Excellent "It was great to have so many amenities on site. It felt like a home away from home. " [](https://expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information) ## Frequently asked questions ### What should I expect on my historical trip to Windsor? ### How many historical hotels are there in Windsor? ### What are the most important historical places and other sights to visit in Windsor? ### What is a historic hotel like in Windsor? ### What is the difference between a historic hotel and a heritage hotel? ### Do historic hotels in Windsor have modern facilities? ## 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) - 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