Title: 10 Historic Hotels in Windsor County for 2026 | Expedia.ca [Windsor County Hotels](https://expedia.ca/Destinations-In-Windsor-County.d553248635976432508.Hotel-Destinations)[Vacation Rentals in Windsor County](https://expedia.ca/Destinations-In-Windsor-County.d553248635976432508.Vacation-Rental-Destinations)[Windsor County Car Rentals](https://expedia.ca/Destinations-In-Windsor-County.d553248635976432508.Car-Rental-Destinations)[Windsor County Vacations](https://expedia.ca/Windsor-County.d553248635976432508.Destination-Travel-Guides) ![](https://images.trvl-media.com/place/3000459649/24ffd150-771e-42f6-8fd9-a3002aef691c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Rachel Samanyi ![](https://images.trvl-media.com/place/3000459649/24ffd150-771e-42f6-8fd9-a3002aef691c.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 ## Top Cities in Windsor County ![aerial view of the Quechee Covered Bridge, over the Ottauquechee River, Quechee Vermont](https://images.trvl-media.com/place/89014/92c0e546-2b37-46d6-9961-c387fdf435b7.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Chester [](https://expedia.ca/Chester-Hotels-Historic-Hotel.0-0-d89014-tHistoricHotel.Travel-Guide-Filter-Hotels) ![](https://images.trvl-media.com/place/10868/c2d6773f-8f3f-4c1a-b710-f2f2bceab647.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Woodstock [](https://expedia.ca/Woodstock-Hotels-Historic-Hotel.0-0-d10868-tHistoricHotel.Travel-Guide-Filter-Hotels) ![](https://images.trvl-media.com/place/8496/505d08ac-b11f-4f25-a539-2958ea0722b2.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Ludlow [](https://expedia.ca/Ludlow-Hotels-Historic-Hotel.0-0-d8496-tHistoricHotel.Travel-Guide-Filter-Hotels) ![Aerial view of the Connecticut River snaking through a vibrant tapestry of fall foliage near a golf course and lake, White River Junction, Vermont, United States.](https://images.trvl-media.com/place/6294/3faa9380-8c50-4f99-bfe3-7ec18f6d3576.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### White River Junction [](https://expedia.ca/White-River-Junction-Hotels-Historic-Hotel.0-0-d6294-tHistoricHotel.Travel-Guide-Filter-Hotels) ![](https://images.trvl-media.com/place/9580/a3d99a95-3156-473d-99ae-f796cac4afe4.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Quechee [](https://expedia.ca/Quechee-Hotels-Historic-Hotel.0-0-d9580-tHistoricHotel.Travel-Guide-Filter-Hotels) ![A small village on the edge of a peninsula with trees and houses reflecting in the calm bay water, Prince Edward Island, Canada](https://images.trvl-media.com/place/6023399/d2b7795d-f2ec-496f-8ad6-83ab36f98f0b.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Cavendish [](https://expedia.ca/Cavendish-Hotels-Historic-Hotel.0-0-d6023399-tHistoricHotel.Travel-Guide-Filter-Hotels) ![Paine Mountain](https://images.trvl-media.com/place/184063/fd3e4c3f-7b8d-43ea-be6c-7ecb5c63234e.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Norwich [](https://expedia.ca/Norwich-Hotels-Historic-Hotel.0-0-d184063-tHistoricHotel.Travel-Guide-Filter-Hotels) ![Aerial Landscape of Maplewood New Jersey ](https://images.trvl-media.com/place/10292/282dfab9-19e2-451d-9dfa-ba7a7807a4e7.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Springfield [](https://expedia.ca/Springfield-Hotels-Historic-Hotel.0-0-d10292-tHistoricHotel.Travel-Guide-Filter-Hotels) ![Cornish-Windsor Covered Bridge](https://images.trvl-media.com/place/7881/cd323da6-a215-45d8-82e1-e1768184197a.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Windsor [](https://expedia.ca/Windsor-Hotels-Historic-Hotel.0-0-d7881-tHistoricHotel.Travel-Guide-Filter-Hotels) ## Check availability on Windsor County Historic Hotels Tonight [Apr 2 - Apr 3](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-04-02&endDate=2026-04-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Apr 3 - Apr 4](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-04-03&endDate=2026-04-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-04-03&endDate=2026-04-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2026-04-10&endDate=2026-04-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&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%2FDestinations-In-Windsor-County-Historic-Hotel.0-0-d553248635976432508-tHistoricHotel.Hotel-Filter-Destinations)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Windsor-County-Historic-Hotel.0-0-d553248635976432508-tHistoricHotel.Hotel-Filter-Destinations) ## Top Windsor County Hotel Reviews ![Main and Mountain Bar & Motel](https://images.trvl-media.com/lodging/22000000/21870000/21860900/21860884/e0f25183_y.jpg) ### Main and Mountain Bar & Motel 6/10 Okay "There is no lobby, no one on site, and they don't answer the phone. It took a while to figure out but there was an email buried in my spam folder about how to check in. Good idea I guess but there was a bunch of wandering around a dark property trying to figure out what to do" [](https://expedia.ca/Ludlow-Hotels-Main-And-Mountain-Bar-Motel.h21860884.Hotel-Information) ![Best Western Springfield Hotel](https://images.trvl-media.com/lodging/1000000/20000/17800/17753/d8a154ae_y.jpg) ### Best Western Springfield Hotel 8/10 Good "Breakfast had lot of options Room was good Always stay there" [](https://expedia.ca/Springfield-Hotels-Best-Western-Springfield-Hotel.h17753.Hotel-Information) ![Fullerton Inn](https://images.trvl-media.com/lodging/16000000/15850000/15845400/15845368/662925ab_y.jpg) ### Fullerton Inn 8/10 Good "The staff were so friendly and helpful...made us feel very welcome. There was no television in our room, which was no problem...just wish we had known in advance. Then we could have brought a good book or crossword puzzle!" [](https://expedia.ca/Chester-Hotels-Fullerton-Inn.h15845368.Hotel-Information) ![The Jackson ](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/6aabd3c1_y.jpg) ### The Jackson 10/10 Excellent "Yes, breakfast was delicious with a good amount of options for all." [](https://expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information) ![Hotel Coolidge](https://images.trvl-media.com/lodging/2000000/1110000/1100200/1100199/2db4f9a7_y.jpg) ### Hotel Coolidge 8/10 Good "Room was nice and clean, staff was lovely and parking was okay. " [](https://expedia.ca/White-River-Junction-Hotels-Hotel-Coolidge.h1100199.Hotel-Information) ![Norwich Inn](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519573/30ba8066_y.jpg) ### Norwich Inn 6/10 Okay "OK stay. Glad there are plenty of other lodging options in the area becuase this one won't be used in the future." [](https://expedia.ca/Norwich-Hotels-Norwich-Inn.h2519573.Hotel-Information) ![Pointe at Castle Hill Resort](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/b9b1ed95_y.jpg) ### Pointe at Castle Hill Resort 8/10 Good "Have stayed here many times. Close to town and Okemo. Very convenient." [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.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 "I recommend it nice rooms and area around the property. Convenient for skiing. " [](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ![Sleep Woodstock Motel](https://images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/9d3fcb33_y.jpg) ### Sleep Woodstock Motel 8/10 Good "A good stay, comfortable beds, nice bathroom, keurig didn’t work, dog poop not picked up across the driveway, but a good alternative near an expensive town. Great to allow dogs, just clear some dog owners not so great. Overall, very good." 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