Title: Windsor Chalets from CA $975 | 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) ![A neat place to walk around an explore](https://images.trvl-media.com/place/7881/9675231b-9d1e-4af8-9ac0-4a4684345ff1.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by mike dobias ![](https://images.trvl-media.com/place/7881/9675231b-9d1e-4af8-9ac0-4a4684345ff1.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 prices for these dates In two weeks [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=7881&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Windsor chalets ![Outdoor dining](https://images.trvl-media.com/lodging/124000000/123270000/123267000/123266945/e9ee5480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/124000000/123270000/123267000/123266945/45bdedf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/124000000/123270000/123267000/123266945/fa430ab3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/124000000/123270000/123267000/123266945/8cd00c8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fabulous 4-bedroom chalet in tranquil Killington getaway with gorgeous Hot tub [](https://www.expedia.ca/Killington-Hotels-Fabulous-4-Bedroom-Chalet-In-Tranquil-Killington-Getaway-With-Gorgeous-Hot-Tub.h123266945.Hotel-Information) North Sherburne 7.4/10 Good (3 reviews) "Great layout for our family of five!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer P. CA $343 CA $797 total includes taxes & fees Feb 12 - Feb 13 [](https://www.expedia.ca/Killington-Hotels-Fabulous-4-Bedroom-Chalet-In-Tranquil-Killington-Getaway-With-Gorgeous-Hot-Tub.h123266945.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/107000000/106160000/106157400/106157385/63238a28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/107000000/106160000/106157400/106157385/0df9f82e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/107000000/106160000/106157400/106157385/ad2f042c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/107000000/106160000/106157400/106157385/0c516aaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington [](https://www.expedia.ca/Plymouth-Hotels-BIGFOOT-CHALET.h106157385.Hotel-Information) Plymouth 10/10 Exceptional (14 reviews) "We had a great stay! Beautiful spot tucked in the woods. Great host communication!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julie-Anne B. CA $415 CA $975 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Plymouth-Hotels-BIGFOOT-CHALET.h106157385.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/69000000/68860000/68850200/68850104/398175e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/69000000/68860000/68850200/68850104/40bc0fc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/69000000/68860000/68850200/68850104/2a2bd0e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/69000000/68860000/68850200/68850104/13b3aaae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 4bd - Ski Okemo, Killington, Magic & Bromley [](https://www.expedia.ca/Chester-Hotels-Spacious-Chalet-For-Picturesque-Fall-Getaway-Winter-Fun-At-Okemo.h68850104.Hotel-Information) Chester 10/10 Exceptional (11 reviews) "We had a really sweet stay here. It was cozy and comfortable, and had everything as advertised. Plenty of towels and kitchen supplies when we needed them, and the beds were comfortable. We had a great trip to Okemo!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carla C. [](https://www.expedia.ca/Chester-Hotels-Spacious-Chalet-For-Picturesque-Fall-Getaway-Winter-Fun-At-Okemo.h68850104.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/108000000/107260000/107257700/107257611/f34d73ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/108000000/107260000/107257700/107257611/2171e7a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/108000000/107260000/107257700/107257611/68751e99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107260000/107257700/107257611/bdccca36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted ski rentals. [](https://www.expedia.ca/Killington-Hotels-West-Park-Chalet-At-Killington-Great-For-Groups-Hot-Tub.h107257611.Hotel-Information) Killington 8.8/10 Excellent (3 reviews) "Great location and ski house layout. Pool Table Rec Room, TV Rec Room and Hot Tub." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rob S. CA $726 CA $1,741 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Killington-Hotels-West-Park-Chalet-At-Killington-Great-For-Groups-Hot-Tub.h107257611.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71220000/71210400/71210361/6b929cac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video-game console](https://images.trvl-media.com/lodging/72000000/71220000/71210400/71210361/8739f051.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video-game console](https://images.trvl-media.com/lodging/72000000/71220000/71210400/71210361/82ff64ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71220000/71210400/71210361/78a0fe57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### BearVaria- Hot Tub, Fireplace, Close to Trails! [](https://www.expedia.ca/Killington-Hotels-BearVaria-4BR-Great-Location.h71210361.Hotel-Information) Killington 10/10 Exceptional (9 reviews) "Great quite location near restaurants and 5 mins from the slopes. The kids loved the little arcade area and the hot tub was great for after skiing. Furniture was a little outdated but met our needs for a fun family vacation" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Uyen B. CA $2,116 CA $3,165 total includes taxes & fees Jan 30 - Jan 31 [](https://www.expedia.ca/Killington-Hotels-BearVaria-4BR-Great-Location.h71210361.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/108000000/107230000/107229500/107229459/7e8d3365.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107230000/107229500/107229459/de4ddd36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107230000/107229500/107229459/720c9070.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![8 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107230000/107229500/107229459/6332a57a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bigelow Chalet at Killington: 8BR/4.5 BA Pet Friendly Home w/ Hot Tub, Fireplace. [](https://www.expedia.ca/Killington-Hotels-Bigelow-Chalet-At-Killington-8BR45-BA-Pet-Friendly-Home-W-Hot-Tub.h107229459.Hotel-Information) Killington 8.0/10 Very good (2 reviews) "Awesome property and very responsive staff! Highly recommended. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anthony P. CA $936 CA $2,239 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Killington-Hotels-Bigelow-Chalet-At-Killington-8BR45-BA-Pet-Friendly-Home-W-Hot-Tub.h107229459.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89990000/89982100/89982066/400cdd0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89990000/89982100/89982066/1e901d44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89990000/89982100/89982066/1a4e96ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/90000000/89990000/89982100/89982066/ecac89c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### BearHaus-Fireplace, HUGE indoor Hot Tub, Sleeps 14 [](https://www.expedia.ca/Killington-Hotels-BearHaus-New-Reno.h89982066.Hotel-Information) Killington 9.6/10 Exceptional (5 reviews) "Great property - excellent hosts. Close to mountain and restaurants" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric D. CA $749 CA $1,684 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Killington-Hotels-BearHaus-New-Reno.h89982066.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/97000000/96030000/96029800/96029719/6b02a563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96030000/96029800/96029719/c588c075.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dishwasher, electric kettle, spices, dining tables](https://images.trvl-media.com/lodging/97000000/96030000/96029800/96029719/31ea8443.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/97000000/96030000/96029800/96029719/8e8c7e4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Overlook - Hot Tub, Game Room, 5min to MTN [](https://www.expedia.ca/Killington-Hotels-The-Overlook-Hot-Tub.h96029719.Hotel-Information) Killington 10/10 Exceptional (2 reviews) "We stayed at the overlook for a family ski trip. It was the perfect place for our family of 4 with 2 young kids. The house was well appointed and what we expected, our hosts communicated well and it was an easy drive to killington mountain every day to ski." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matt F. CA $1,384 CA $2,447 total includes taxes & fees Feb 12 - Feb 13 [](https://www.expedia.ca/Killington-Hotels-The-Overlook-Hot-Tub.h96029719.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=2026-02-05&endDate=2026-02-06®ionId=7881&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Vermont%2C+United+States+of+America®ionId=7881&latLong=43.48%2C-72.386566&adults=2&startDate=2026-04-22&d1=2026-04-22&endDate=2026-04-25&d2=2026-04-25&lodging=CABIN) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Vermont%2C+United+States+of+America®ionId=7881&latLong=43.48%2C-72.386566&adults=2&startDate=2026-04-22&d1=2026-04-22&endDate=2026-04-25&d2=2026-04-25&lodging=COTTAGE) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Vermont%2C+United+States+of+America®ionId=7881&latLong=43.48%2C-72.386566&adults=2&startDate=2026-04-22&d1=2026-04-22&endDate=2026-04-25&d2=2026-04-25&lodging=VACATION_HOME) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Vermont%2C+United+States+of+America®ionId=7881&latLong=43.48%2C-72.386566&adults=2&startDate=2026-04-22&d1=2026-04-22&endDate=2026-04-25&d2=2026-04-25&lodging=APART_HOTEL) Condos [](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Vermont%2C+United+States+of+America®ionId=7881&latLong=43.48%2C-72.386566&adults=2&startDate=2026-04-22&d1=2026-04-22&endDate=2026-04-25&d2=2026-04-25&lodging=CONDO) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Vermont%2C+United+States+of+America®ionId=7881&latLong=43.48%2C-72.386566&adults=2&startDate=2026-04-22&d1=2026-04-22&endDate=2026-04-25&d2=2026-04-25&lodging=APARTMENT) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Vermont%2C+United+States+of+America®ionId=7881&latLong=43.48%2C-72.386566&adults=2&startDate=2026-04-22&d1=2026-04-22&endDate=2026-04-25&d2=2026-04-25&lodging=CHALET) Villas [](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Vermont%2C+United+States+of+America®ionId=7881&latLong=43.48%2C-72.386566&adults=2&startDate=2026-04-22&d1=2026-04-22&endDate=2026-04-25&d2=2026-04-25&lodging=VILLA) ![](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%2FWindsor-Chalets.d7881-aaChalets.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindsor-Chalets.d7881-aaChalets.Travel-Guide-Accommodation) ## Top Windsor Hotel Reviews ![Holiday Inn Express Hotel & Suites White River Junction by IHG](https://images.trvl-media.com/lodging/2000000/1140000/1138300/1138208/634c6a80_y.jpg) ### Holiday Inn Express Hotel & Suites White River Junction by IHG 10/10 Excellent "great" [](https://expedia.ca/White-River-Junction-Hotels-Holiday-Inn-Express-Hotel-Suites-White-River-Junction.h1138208.Hotel-Information) ![North Star Lodge and Resort](https://images.trvl-media.com/lodging/1000000/190000/185900/185873/0612ebf1_y.jpg) ### North Star Lodge and Resort 10/10 Excellent "Awesome customer service- great room" [](https://expedia.ca/Killington-Hotels-North-Star-Lodge-And-Resort.h185873.Hotel-Information) ![Summit Lodge](https://images.trvl-media.com/lodging/2000000/1110000/1102600/1102506/5da3617c_y.jpg) ### Summit Lodge 10/10 Excellent "Clean room, good, free breakfast, and cute social areas." [](https://expedia.ca/Killington-Hotels-Summit-Lodge.h1102506.Hotel-Information) ![The Shire Woodstock](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg) ### The Shire Woodstock 10/10 Excellent "Cozy comfortable room for a fair price. Easy check-in and check-out." [](https://expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.Hotel-Information) ![Holiday Inn Club Vacations Mount Ascutney Resort by IHG](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/fead325a_y.jpg) ### Holiday Inn Club Vacations Mount Ascutney Resort by IHG 10/10 Excellent "Fantastic! Easy check in and out! Rooms were updated and spotless. Great customer service!" [](https://expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.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 "Everyone was friendly, courteous, and helpful. Room was very clean. Restaurant and bar had live music. Overall place was A+" [](https://expedia.ca/Killington-Hotels-The-Mountain-Inn-At-Killington.h975389.Hotel-Information) ![Pointe at Castle Hill Resort](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/6a80e6c5_y.jpg) ### Pointe at Castle Hill Resort 10/10 Excellent "Everything/everyone was superb!!! " [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![Fireside Inn & Suites West Lebanon](https://images.trvl-media.com/lodging/1000000/20000/12300/12300/adb27d13_y.jpg) ### Fireside Inn & Suites West Lebanon 10/10 Excellent "The room was very clean. Isaac.Delivered my room Service and he was very nice and made sure I received everything. Thank you so much. I will stay there again. " [](https://expedia.ca/Lebanon-Hotels-Fireside-Inn-Suites-West-Lebanon.h12300.Hotel-Information) ![Align Inn Vermont](https://images.trvl-media.com/lodging/1000000/10000/1200/1108/996cad8e_y.jpg) ### Align Inn Vermont 10/10 Excellent "Clean, quiet, good breakfast. Check in was easy and staff was friendly. " [](https://expedia.ca/Quechee-Hotels-Quality-Inn-At-Quechee-Gorge.h1108.Hotel-Information) ## Find out more about Windsor ## Windsor Chalets information | Number of reviews | 25 | | ----------------- | ---------- | | Accommodation | 46 Chalets | | Lowest Price | CA $975 | | Highest Price | CA $3,165 | ## 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) - [Romantic Hotels in Ascutney ](https://www.expedia.ca/Ascutney-Hotels-Romantic-Hotel.0-0-d6046953-tRomanticHotel.Travel-Guide-Filter-Hotels) - 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