Title: Book the Best ROMANTIC Hotels in Windsor, VT from CA $250 - Windsor Romantic Getaways | 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 Romantic Hotels Tonight [Mar 12 - Mar 13](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2026-03-12&endDate=2026-03-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Mar 13 - Mar 14](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2026-03-13&endDate=2026-03-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) This weekend [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2026-03-13&endDate=2026-03-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2026-03-20&endDate=2026-03-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Our top choices for Windsor romantic hotels ![Exterior](https://images.trvl-media.com/lodging/28000000/27120000/27117200/27117112/62670e78.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) ![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) ![Interior](https://images.trvl-media.com/lodging/28000000/27120000/27117200/27117112/b81f74eb.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 (167 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 $231 CA $499 total includes taxes & fees Mar 16 - Mar 17 [](https://www.expedia.ca/Grafton-Hotels-Charming-Fully-Renovated-One-Room-Schoolhouse-On-22-Acres.h27117112.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/23000000/22770000/22769000/22768970/a93fa1dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/23000000/22770000/22769000/22768970/329af4b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/23000000/22770000/22769000/22768970/67c634a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/23000000/22770000/22769000/22768970/a4957511.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route [](https://www.expedia.ca/Ludlow-Hotels-Beautifully-Updated-Unique-Village-Home.h22768970.Hotel-Information) Ludlow 9.8/10 Exceptional (85 reviews) "We had a great stay at this home for a long weekend skiing at Okemo. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa W. CA $303 CA $612 total includes taxes & fees Apr 7 - Apr 8 [](https://www.expedia.ca/Ludlow-Hotels-Beautifully-Updated-Unique-Village-Home.h22768970.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 (106 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 $219 CA $433 total includes taxes & fees Apr 7 - Apr 8 [](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) ![Property grounds](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131894/77b10ad2.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) ### 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 (28 reviews) "Overall very clean and nice. Needs some updating like more spoons, only 2, bigger coffee cups. And a new coffee table that is very worn. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David A. CA $97 CA $345 total includes taxes & fees Apr 8 - Apr 9 [](https://www.expedia.ca/Ludlow-Hotels-Ski-InOut-Condo-With-Patio.h72131894.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) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/23000000/22870000/22865900/22865847/faf90773.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) ![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 (107 reviews) "Had a wonderful stay. Clean,well kept and cozy." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edwin G. CA $303 CA $612 total includes taxes & fees Apr 7 - Apr 8 [](https://www.expedia.ca/Ludlow-Hotels-Short-Walk-To-Shops.h22865847.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/62000000/61640000/61636400/61636331/790c70e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/62000000/61640000/61636400/61636331/82f89163.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/62000000/61640000/61636400/61636331/191f5e92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/62000000/61640000/61636400/61636331/4ed0f838.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street [](https://www.expedia.ca/Ludlow-Hotels-Downtown-Condo-W-Electric-Fireplace.h61636331.Hotel-Information) Ludlow 9.0/10 Wonderful (25 reviews) "Great rate for a place with all the basics!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Macgregor CA $155 CA $369 total includes taxes & fees Apr 7 - Apr 8 [](https://www.expedia.ca/Ludlow-Hotels-Downtown-Condo-W-Electric-Fireplace.h61636331.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/75000000/74110000/74100200/74100124/bd9e5999.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/75000000/74110000/74100200/74100124/a9f17f8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Internet, bed sheets](https://images.trvl-media.com/lodging/75000000/74110000/74100200/74100124/023bb657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74110000/74100200/74100124/b6513e83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Studio Condo with Great Location, WiFi & Kitchenette [](https://www.expedia.ca/Ludlow-Hotels-Cozy-Studio-Condo-With-Great-Location.h74100124.Hotel-Information) Ludlow 8.8/10 Excellent (31 reviews) "Great location and great place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda G. CA $143 CA $318 total includes taxes & fees Mar 18 - Mar 19 [](https://www.expedia.ca/Ludlow-Hotels-Cozy-Studio-Condo-With-Great-Location.h74100124.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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/73000000/72610000/72603600/72603570/dd5b1f55.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 $172 CA $250 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) ![Property grounds](https://images.trvl-media.com/lodging/39000000/38200000/38197000/38196993/5f7ca819.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) ![Interior](https://images.trvl-media.com/lodging/39000000/38200000/38197000/38196993/w1999h1332x1y1-b15a3da9.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 $172 CA $250 total includes taxes & fees Mar 24 - Mar 25 [](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) ![Pool](https://images.trvl-media.com/lodging/39000000/38320000/38314400/38314377/w2000h1332x0y1-5869c686.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) ![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 $172 CA $250 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Bridgewater-Corners-Hotels-107-Deluxe-Studio-Queen.h38314377.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=2026-03-26&endDate=2026-03-27®ionId=7881&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ![](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 ![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 "Great place! Close to the mountain and restaurants on access road. " [](https://expedia.ca/Killington-Hotels-Killington-Mountain-Lodge.h103640.Hotel-Information) ![The Mountain Inn at Killington](https://images.trvl-media.com/lodging/1000000/980000/975400/975389/29356441_y.jpg) ### The Mountain Inn at Killington 10/10 Excellent "Love staying here. Staff is amazing! Super attentive. Great food at the restaurant. Cozy lodge feel. Basically on the mountain Without being ski in ski out. This is where I always stay when visiting killington. " [](https://expedia.ca/Killington-Hotels-The-Mountain-Inn-At-Killington.h975389.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 "Very clean, spacious rooms, very apartment like. Everything we needed to have a great girls weekend the pool was enormous and very warm beautiful grounds. The kitchen had everything we needed to cook meals. The staff was wonderful during check-in. The room had everything we needed. Didn’t need to call them again." [](https://expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.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) ![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 "Yes" [](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 "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 ### Searching for romantic hotels in Windsor? ### When is the best time of year for a romantic getaway to Windsor? ### What is there to do in Windsor? ### What's the best way to get to Windsor and around town during my romantic getaway? ## 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) - 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