Title: Book the Best Windsor LUXURY Hotels - Upscale Hotels in Windsor, VT | 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 Luxury Hotels Tonight [Mar 15 - Mar 16](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2026-03-15&endDate=2026-03-16&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Mar 16 - Mar 17](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2026-03-16&endDate=2026-03-17&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2026-03-20&endDate=2026-03-22&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) In two weeks [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2026-03-27&endDate=2026-03-29&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AFFINITY_SPRING_PROMO_7881) ## 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 "Great!" [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![Holiday Inn Express Hotel & Suites White River Junction by IHG](https://images.trvl-media.com/lodging/2000000/1140000/1138300/1138208/ffe7105d_y.jpg) ### Holiday Inn Express Hotel & Suites White River Junction by IHG 6/10 Okay "The bed was very uncomfortable and the room was hot" [](https://expedia.ca/White-River-Junction-Hotels-Holiday-Inn-Express-Hotel-Suites-White-River-Junction.h1138208.Hotel-Information) ![Mountain Sports Inn](https://images.trvl-media.com/lodging/2000000/1340000/1339900/1339833/fae277d0_y.jpg) ### Mountain Sports Inn 10/10 Excellent "It was great" [](https://expedia.ca/Killington-Hotels-Mountain-Sports-Inn.h1339833.Hotel-Information) ![Killington Mountain Lodge, Tapestry Collection by Hilton](https://images.trvl-media.com/lodging/1000000/110000/103700/103640/f9bd2dd9_y.jpg) ### Killington Mountain Lodge, Tapestry Collection by Hilton 10/10 Excellent "Near skiing!!" [](https://expedia.ca/Killington-Hotels-Killington-Mountain-Lodge.h103640.Hotel-Information) ![North Star Lodge and Resort](https://images.trvl-media.com/lodging/1000000/190000/185900/185873/17fcad53_y.jpg) ### North Star Lodge and Resort 10/10 Excellent "Nice place to stay and room had a view of Superstar slope. " [](https://expedia.ca/Killington-Hotels-North-Star-Lodge-And-Resort.h185873.Hotel-Information) ![Fireside Inn & Suites West Lebanon](https://images.trvl-media.com/lodging/1000000/20000/12300/12300/43f4036d_y.jpg) ### Fireside Inn & Suites West Lebanon 8/10 Good "Great breakfast, and pool / hot tub. Atrium with coy pond and turtles inside. Close to everything. Multiple rooms have massage chairs. Gift shop was stocked well too." [](https://expedia.ca/Lebanon-Hotels-Fireside-Inn-Suites-West-Lebanon.h12300.Hotel-Information) ![Align Inn Vermont](https://images.trvl-media.com/lodging/1000000/10000/1200/1108/4cc53d97_y.jpg) ### Align Inn Vermont 10/10 Excellent "Clean room" [](https://expedia.ca/Quechee-Hotels-Quality-Inn-At-Quechee-Gorge.h1108.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 10/10 Excellent "Great location. I stay often." [](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 "The breakfast and staff were AMAZING! Freshly made scrambled eggs, bacon, sausage patties, french toast, waffles, Cabot yogurt with all the fixings, dry cereal, hot oatmeal, breads, muffins, danish, etc. Everything was delicious and well presented as well! Forgot to mention freshly gound coffee! YUM! KUDOS!" [](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ## Frequently asked questions ### Which area of Windsor is best to stay in for luxury hotels? > This part of Windsor is the heart of the town, offering a blend of historic charm and modern conveniences. Main Street itself is lined with beautifully maintained 19th-century buildings, local shops, and eateries. It's a very walkable area, with landmarks like the Windsor-Cornish Covered Bridge and the American Precision Museum just a short stroll away. > > > Couples looking for a refined getaway will find this area particularly appealing. The luxury hotels here often feature elegant design, fine dining options, and personal service, making for a relaxing and indulgent experience. You'll be well-placed to explore local attractions like the Harpoon Brewery or take a scenic drive along the Connecticut River. > > > Solo travellers seeking comfort and quality will also appreciate staying in this central area. The convenience of having everything within walking distance, from quality restaurants to cultural sites, means you can enjoy a stress-free trip focusing on relaxation and exploration. Many luxury hotels in this area also offer high-end fitness equipment and spa services. ### How much does a luxury hotel in Windsor cost? ### What luxury activities and experiences are there in Windsor? > This area is the heart of Windsor, offering a blend of historic charm and convenient access to upscale amenities. You'll find well-preserved 19th-century architecture, with many buildings now housing boutique shops and fine dining establishments. The village is compact and walkable, with the Connecticut River just a short stroll away. > > > For couples seeking a refined escape, staying in the village provides easy access to intimate dining experiences at restaurants focusing on local, seasonal ingredients. Many of these establishments offer curated wine lists to complement their menus. Additionally, the area is home to unique art galleries featuring regional artists, superb for an afternoon of browsing. > > > Travellers interested in exclusive experiences will find opportunities for private tastings at local craft breweries or distilleries, often with behind-the-scenes tours. ### How can I save on a luxury hotel in Windsor with Expedia? ### Is it cheaper to book a luxury Windsor hotel and flights as a package? ### Can I cancel my luxury hotel reservation on Expedia? ## 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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