Title: Rupert Chalets from CA $1,099 | Expedia.ca [Rupert Travel Guide](https://expedia.ca/Rupert.dx3000459728)[Hotels in Rupert](https://expedia.ca/Rupert-Hotels.d3000459728.Travel-Guide-Hotels)[Vacation Rentals in Rupert](https://expedia.ca/Rupert-Vacation-Rentals.d3000459728.Travel-Guide-VacationRentals)[Rupert Car Rentals](https://expedia.ca/Car-Rentals-In-Rupert.d3000459728.Car-Rental-Guide)[Rupert Vacation Packages](https://expedia.ca/Rupert.d3000459728.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Chalets in Rupert from CA $1,099 - ![](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 Next weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=3000459728&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=3000459728&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=3000459728&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 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=3000459728&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Rupert chalets ![Exterior](https://images.trvl-media.com/lodging/76000000/75640000/75637200/75637196/0542e546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/76000000/75640000/75637200/75637196/b79b59cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/76000000/75640000/75637200/75637196/e9b666aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75640000/75637200/75637196/20ca1ec7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres [](https://www.expedia.ca/Stratton-Hotels-HYGGE-HOUSE-Green-Mountain-Chalet-With-Sauna-And-Treehouse.h75637196.Hotel-Information) Stratton 10/10 Exceptional (5) "We had an amazing stay. It was the perfect location for 4 couples. The owners were super responsive. Amenities were great (our only kitchen recommendation is a non-glass cutting board and individual salt and pepper shakers). Would love to stay again in the summer next time! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicholas D. CA $526 CA $1,099 total includes taxes & fees Jan 13 - Jan 14 [](https://www.expedia.ca/Stratton-Hotels-HYGGE-HOUSE-Green-Mountain-Chalet-With-Sauna-And-Treehouse.h75637196.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/121000000/120430000/120430000/120429915/a3e005f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120430000/120430000/120429915/w2396h1629x0y0-21164ff5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/121000000/120430000/120430000/120429915/cc9b5501.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/121000000/120430000/120430000/120429915/dd28f119.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stratton A-Frame: Boot Warmers EV Hot Tub Sauna,1 Gbps, Manchester Okemo MT Snow [](https://www.expedia.ca/Jamaica-Hotels-PreLaunch-A-Frame-Hot-Tub-Sauna-EV-Stratton.h120429915.Hotel-Information) Jamaica 10/10 Exceptional (1) "Couldn't be better! Outstanding! We had our family holiday ski trip from Dec 25-29th,2025\. The amenities were second to none. The hot tub, sauna and fire pit made the winter warm! The house was clean comfortable and very cozy. The kitchen was extremely well appointed (sharp knives!). The staples available (coffee, tea, oil, spices etc.) were high quality and the best I've ever experienced in a short term rental. The beds and bedding were very comfortable! Most immortality the hosts were very... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laird N. CA $875 CA $1,119 total includes taxes & fees Jan 13 - Jan 14 [](https://www.expedia.ca/Jamaica-Hotels-PreLaunch-A-Frame-Hot-Tub-Sauna-EV-Stratton.h120429915.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=2026-01-21&endDate=2026-01-22®ionId=3000459728&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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%2FRupert-Chalets.d3000459728-aaChalets.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FRupert-Chalets.d3000459728-aaChalets.Travel-Guide-Accommodation) ## Top Rupert Hotel Reviews ![Aspen At Manchester](https://images.trvl-media.com/lodging/11000000/10260000/10254500/10254459/6f88107a_y.jpg) ### Aspen At Manchester 10/10 Excellent "Clean room and nice staff! Great TV" [](https://expedia.ca/Bennington-Hotels-Aspen-At-Manchester.h10254459.Hotel-Information) ![Hampton Inn and Suites Manchester](https://images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/5bd509a3_y.jpg) ### Hampton Inn and Suites Manchester 10/10 Excellent "Good experience!" [](https://expedia.ca/Bennington-Hotels-Hampton-Inn-And-Suites-Manchester.h18188804.Hotel-Information) ![COHO Inn & Motor Lodge](https://images.trvl-media.com/lodging/105000000/104400000/104395800/104395732/3f7fd5fb_y.jpg) ### COHO Inn & Motor Lodge 10/10 Excellent "A cozy inn with a warm, rustic atmosphere (wood burning stove) surrounded by beautiful Vermont countryside. The inn is owned and operated by a friendly family who gave us helpful advice on restaurants in the area. Breakfasts were great. Vermont maple syrup! It's a 20-minute drive from Okemo, but the drive was worthwhile. If we return to the area we will stay here again." [](https://expedia.ca/Weston-Hotels-The-Colonial-House-Inn-And-Motor-Lodge.h104395732.Hotel-Information) ![Toll Road Inn](https://images.trvl-media.com/lodging/8000000/7660000/7652200/7652200/94368990_y.jpg) ### Toll Road Inn 10/10 Excellent "My husband and I stayed with our two children (3 & 5). The owner Mike was extremely kind and helpful. The room was adorable, and perfect for what we needed. They very conveniently offered 24/7 coffee and a welcoming lobby area. I can confidently say the next time I go up to that area I will be booking a room here again. Furthermore it will be the first and only place I recommend to friends and family staying in this area as well. Thank you for the hospitality and style! " [](https://expedia.ca/Bennington-Hotels-Toll-Road-Inn.h7652200.Hotel-Information) ![The Olympia Lodge](https://images.trvl-media.com/lodging/10000000/9260000/9257700/9257616/c701f02d_y.jpg) ### The Olympia Lodge 10/10 Excellent "Updated room; friendly staff; great breakfast" [](https://expedia.ca/Bennington-Hotels-The-Olympia-Lodge.h9257616.Hotel-Information) ![Kimpton Taconic Hotel by IHG](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572989/72cb9377_y.jpg) ### Kimpton Taconic Hotel by IHG 10/10 Excellent "Stayed here twice. Both times were excellent. Dogs are welcomed and they do a great job making your pets feel welcomed as well." [](https://expedia.ca/Bennington-Hotels-Kimpton-Taconic-Hotel.h1572989.Hotel-Information) ![The Reluctant Panther Inn and Restaurant](https://images.trvl-media.com/lodging/4000000/3910000/3908500/3908442/8359157a_y.jpg) ### The Reluctant Panther Inn and Restaurant 10/10 Excellent "Room was well appointed and spacious, clean and comfortable" [](https://expedia.ca/Bennington-Hotels-The-Reluctant-Panther-Inn-And-Restaurant.h3908442.Hotel-Information) ![Weathervane Motel](https://images.trvl-media.com/lodging/11000000/10430000/10429400/10429394/17ddc189_y.jpg) ### Weathervane Motel 10/10 Excellent "Clean room. Quiet, friendly staff " [](https://expedia.ca/Bennington-Hotels-Weathervane-Motel.h10429394.Hotel-Information) ![The Inn at Manchester](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505817/534fcc92_y.jpg) ### The Inn at Manchester 10/10 Excellent "The inn was lovely and the staff was very attentive." [](https://expedia.ca/Bennington-Hotels-The-Inn-At-Manchester.h1505817.Hotel-Information) ## Find out more about Rupert ## Rupert Chalets information | Number of reviews | | | ----------------- | ---------- | | Accommodation | 36 Chalets | | Lowest Price | CA $1,099 | | Highest Price | CA $1,119 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [2 Star Hotels in Manchester ](https://www.expedia.ca/2Star-Manchester-Hotels.s20-0-d129374.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Danby ](https://www.expedia.ca/3Star-Danby-Hotels.s30-0-d6034870.Travel-Guide-Filter-Hotels) - [4 Star Hotels in West Arlington ](https://www.expedia.ca/4Star-West-Arlington-Hotels.s40-0-d553248635976385881.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Manchester ](https://www.expedia.ca/5Star-Manchester-Hotels.s50-0-d129374.Travel-Guide-Filter-Hotels) - [Danby Hotels ](https://www.expedia.ca/Danby-Hotels.d6034870.Travel-Guide-Hotels) - 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