Title: 10 Best Windsor County Luxury Resorts & Hotels for 2025 | 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) ![Okemo Valley Golf Club showing forests, a luxury hotel or resort and autumn colours](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/147000/147798-Okemo-Mountain-Resort-And-Golf-Club.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Luxury Hotels & Resorts in Windsor County ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 ![Ludlow showing street scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/94000/94298-Ludlow.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Ludlow [](https://expedia.ca/Ludlow-Hotels-Luxury-Hotel.0-0-d8496-tLuxuryHotel.Travel-Guide-Filter-Hotels) ![Woodstock featuring a house](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/94000/94311-Woodstock.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Woodstock [](https://expedia.ca/Woodstock-Hotels-Luxury-Hotel.0-0-d10868-tLuxuryHotel.Travel-Guide-Filter-Hotels) ![](https://mediaim.expedia.com/destination/2/212ecbf3b606238229538e223f3f57eb.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### White River Junction [](https://expedia.ca/White-River-Junction-Hotels-Luxury-Hotel.0-0-d6294-tLuxuryHotel.Travel-Guide-Filter-Hotels) ![Quechee featuring a river or creek, a bridge and tranquil scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/93000/93816-Central-Vermont.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Quechee [](https://expedia.ca/Quechee-Hotels-Luxury-Hotel.0-0-d9580-tLuxuryHotel.Travel-Guide-Filter-Hotels) ![](https://mediaim.expedia.com/destination/2/e6f5a135e5990faead3b19a2481c6d2b.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Windsor [](https://expedia.ca/Windsor-Hotels-Luxury-Hotel.0-0-d7881-tLuxuryHotel.Travel-Guide-Filter-Hotels) ![Central Vermont showing a house](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/94000/94646-Calvin-Coolidge-Historic-Site.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Plymouth [](https://expedia.ca/Plymouth-Hotels-Luxury-Hotel.0-0-d146918-tLuxuryHotel.Travel-Guide-Filter-Hotels) ![Weston](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/94000/94317-Weston.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Weston [](https://expedia.ca/Weston-Hotels-Luxury-Hotel.0-0-d177460-tLuxuryHotel.Travel-Guide-Filter-Hotels) ## Check availability on Windsor County Luxury Hotels Tonight [Sep 22 - Sep 23](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2025-09-22&endDate=2025-09-23&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 23 - Sep 24](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2025-09-23&endDate=2025-09-24&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2025-09-26&endDate=2025-09-28&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2025-10-03&endDate=2025-10-05&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Windsor County Luxury Hotels ![](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-Luxury-Hotel.0-0-d553248635976432508-tLuxuryHotel.Hotel-Filter-Destinations)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Windsor-County-Luxury-Hotel.0-0-d553248635976432508-tLuxuryHotel.Hotel-Filter-Destinations) ## Top Windsor County Hotel Reviews ![Best Western Springfield Hotel](//images.trvl-media.com/lodging/1000000/20000/17800/17753/f0e2c480_y.jpg) ### Best Western Springfield Hotel 10/10 Excellent "Overall there were no issues with my stay. " [](https://expedia.ca/Springfield-Hotels-Best-Western-Springfield-Hotel.h17753.Hotel-Information) ![The Jackson ](//images.trvl-media.com/lodging/1000000/190000/181400/181337/f642c888_y.jpg) ### The Jackson 10/10 Excellent "Excellent Vintage style B&B. " [](https://expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information) ![Align Inn Vermont](//images.trvl-media.com/lodging/1000000/10000/1200/1108/996cad8e_y.jpg) ### Align Inn Vermont 10/10 Excellent "Best hotel in the area, feels like home, the staff are so warm and welcoming, especially Chelsea. She gave us so many local recommendations, the Mexican restaurant next door is excellent. The rooms and cozy and clean. " [](https://expedia.ca/Quechee-Hotels-Quality-Inn-At-Quechee-Gorge.h1108.Hotel-Information) ![The Shire Woodstock](//images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg) ### The Shire Woodstock 10/10 Excellent "." [](https://expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.Hotel-Information) ![Lincoln Inn & Gallery](//images.trvl-media.com/lodging/114000000/113900000/113896300/113896234/5d2c48fa_y.jpg) ### Lincoln Inn & Gallery 10/10 Excellent "Loved our stay here! Beautiful!" [](https://expedia.ca/Woodstock-Hotels-Lincoln-Inn-Gallery.h113896234.Hotel-Information) ![Sleep Woodstock Motel](//images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/7b3a7c11_y.jpg) ### Sleep Woodstock Motel 10/10 Excellent "Very hospitable and well appointed motel, 5 minute drive into woodstock. Very cute. spotlessly clean and had everything you couild need. Note - cannabis dispensary directly next door just FYI" [](https://expedia.ca/Woodstock-Hotels-Sleep-Woodstock-Motel.h9658860.Hotel-Information) ![The Quechee Inn at Marshland Farm](//images.trvl-media.com/lodging/2000000/1930000/1924800/1924710/c8372335_y.jpg) ### The Quechee Inn at Marshland Farm 10/10 Excellent "Beautiful property and large spacious room" [](https://expedia.ca/Quechee-Hotels-The-Quechee-Inn-At-Marshland-Farm.h1924710.Hotel-Information) ![Jackson Gore Village](//images.trvl-media.com/lodging/3000000/2420000/2417100/2417009/7193c148_y.jpg) ### Jackson Gore Village 10/10 Excellent "The hotel was peaceful and clean, perfect for the weekend getaway." [](https://expedia.ca/Ludlow-Hotels-Jackson-Gore-Village.h2417009.Hotel-Information) ![Hotel Coolidge](//images.trvl-media.com/lodging/2000000/1110000/1100200/1100199/w2880h2170x0y0-a69a5404_y.jpg) ### Hotel Coolidge 10/10 Excellent "Great location with great New England vibe. 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