Title: Top Chalets in Simcoe County in 2025 | Expedia.ca [Simcoe County Hotels](https://expedia.ca/Destinations-In-Simcoe-County.d553248635976432418.Hotel-Destinations)[Vacation Rentals in Simcoe County](https://expedia.ca/Destinations-In-Simcoe-County.d553248635976432418.Vacation-Rental-Destinations)[Things to do in Simcoe County](https://expedia.ca/Things-To-Do-In-Simcoe-County.d553248635976432418.Travel-Guide-Activities)[Simcoe County Car Rentals](https://expedia.ca/Destinations-In-Simcoe-County.d553248635976432418.Car-Rental-Destinations)[Simcoe County Vacations](https://expedia.ca/Simcoe-County.d553248635976432418.Destination-Travel-Guides) ![Sunset Point Park which includes general coastal views and a park](https://images.trvl-media.com/place/6166172/a3fbea53-acb4-4c62-9a17-5390da4cee79.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Chalets in Simcoe County ## Compare and save - ![](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 [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248635976432418&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976432418&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976432418&startDate=2026-02-13&endDate=2026-02-15&adults=2&lodging=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976432418&startDate=2026-03-13&endDate=2026-03-15&adults=2&lodging=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Cities in Simcoe County ![Collingwood which includes heritage architecture](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/83000/83072-Barrie-Orillia-And-Vicinity.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Collingwood [](https://expedia.ca/Collingwood-Chalets.d11938-aaChalets.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/3fff0332e4b45368cdac3c6d03e83dec.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Oro-Medonte [](https://expedia.ca/Oro-Medonte-Chalets.d6288963-aaChalets.Travel-Guide-Accommodation) ![Wasaga Beach Provincial Park showing a beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/83000/83440-Wasaga-Beach-Provincial-Park.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Wasaga Beach [](https://expedia.ca/Wasaga-Beach-Chalets.d181914-aaChalets.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/0e85fe6f49a1df9fcd11ec91d1618e70.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Essa [](https://expedia.ca/Essa-Chalets.d553248635740518697-aaChalets.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/74bd4a56ef2df06b8386e4fc337f04d6.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Springwater [](https://expedia.ca/Springwater-Chalets.d553248635740519504-aaChalets.Travel-Guide-Accommodation) ## Featured Chalets in Simcoe County ![Exterior](https://images.trvl-media.com/lodging/102000000/101300000/101299400/101299318/9ddbb35f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101300000/101299400/101299318/383a1fde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101300000/101299400/101299318/f697b586.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101300000/101299400/101299318/67fec7d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Moonstone ski Chalet Moonstone 10/10 Exceptional (7) "Location of this chalet was perfect for skiing. We loved everything about this rental. We will definitely be back for another stay." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Stephanie R. [](https://www.expedia.ca/Oro-Medonte-Hotels-Moonstone-Chalet.h101299318.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101880000/101871000/101870995/2a067a8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101880000/101871000/101870995/9a4f0c74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101880000/101871000/101870995/c0ca648f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101880000/101871000/101870995/fe9bd9df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy, stylish, century home located just steps from Mount St Louis ski hill! Coldwater 10/10 Exceptional (1) "Short stay to go skiing at Mount St. Louis Moonstone, and enjoy dining out in the area (Ktchn). House was as described, clean, organized and comfortable. Little inconvenient to have only a first floor bathroom but it was spacious. Enjoyed our stay." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Carolyn Or Mike G. [](https://www.expedia.ca/Oro-Medonte-Hotels-Cozy.h101870995.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/108000000/107110000/107103600/107103527/44885175.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/108000000/107110000/107103600/107103527/07cca7af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107110000/107103600/107103527/fb1723b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107110000/107103600/107103527/6368dd0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blue Mountain Mansion House Collingwood 9.4/10 Exceptional (3) "It was an overall splendid experience. I would definitely recommend this for anyone looking to have a restful stay and an enjoyable experience. The host was so kind and wonderful during the stay." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Bansy A. [](https://www.expedia.ca/Clearview-Hotels-Blue-Mountain-Mansion-House.h107103527.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/81000000/80030000/80026200/80026172/w1018h683x4y0-2d656c73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/81000000/80030000/80026200/80026172/w906h683x60y0-f58e1fbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/81000000/80030000/80026200/80026172/e9857048.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/81000000/80030000/80026200/80026172/w1024h679x0y4-a70f71ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ❄️YOUR PERFECT COLLINGWOOD/BLUE MOUNTAIN WINTER HOME FINALLY FOUND! Collingwood 10/10 Exceptional (7) "We spent the past several days at Andrea's property with the family. It was a truly fantastic experience as the property was absolutely beautiful, and everything you could possibly require was provided. Andrea was a fantastic host and communication was fantastic. We look forward to returning!" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) George M. [](https://www.expedia.ca/Collingwood-Hotels-Large-Home-Private.h80026172.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/73000000/72100000/72093900/72093809/1bb7e071.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/73000000/72100000/72093900/72093809/4916af16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/73000000/72100000/72093900/72093809/b280c9cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/73000000/72100000/72093900/72093809/a0a29c9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Large family home, minutes from base of Blue Mountain and Osler. Collingwood [](https://www.expedia.ca/Collingwood-Hotels-Large-Family-Home.h72093809.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/73000000/72100000/72094600/72094547/63d1dad9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/73000000/72100000/72094600/72094547/c1e6b0a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/73000000/72100000/72094600/72094547/e07080e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72100000/72094600/72094547/e5c9b22c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 19th century school house, modernized to a family home. Mins from Blue Mountain Collingwood [](https://www.expedia.ca/Collingwood-Hotels-19th-Century-School-House.h72094547.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/35000000/34120000/34111100/34111077/w4608h3283x0y173-dce9ba21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player](https://images.trvl-media.com/lodging/35000000/34120000/34111100/34111077/2d87326f_edited_36f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34120000/34111100/34111077/0ecd27a2_edited_3716.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sport court](https://images.trvl-media.com/lodging/35000000/34120000/34111100/34111077/265cb662.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 bedroom luxury private Cabin located in the Lakes of Wasaga Resort Wasaga Beach 10/10 Exceptional (5) "Highly recommended" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Enz S. [](https://www.expedia.ca/Barrie-Orillia-Hotels-2-Bedroom-Luxury-Private-Cabin-Located-In-The-Lakes-Of-Wasaga-Resort.h34111077.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/84000000/83420000/83410900/83410828/w1632h828x80y0-fc67a5b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/84000000/83420000/83410900/83410828/fb9c57b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83420000/83410900/83410828/2e6873fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player](https://images.trvl-media.com/lodging/84000000/83420000/83410900/83410828/w1678h828x57y0-91597c59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Moonstone Chalet: Your perfect city escape! With Hot tub Moonstone 10/10 Exceptional (1) "The stay was wonderful! Very clean and easy to keep clean as well! Our host was lovely and was available when we had needed her. We booked our little getaway mid-week as I was able to get a day off work so we could travel there. I needed to work the remainder of the week still and was concerned that the internet service may not have been strong enough as I work in a queue and take my calls through the internet/wifi, so strength and stability is extremely important. Our wonderful host assured me... ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Paula G. [](https://www.expedia.ca/Oro-Medonte-Hotels-Moonstone-Chalet-Your-Perfect-City-Escape.h83410828.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89770000/89761400/89761330/33b17d2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89770000/89761400/89761330/w1024h557x0y63-cead3f3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/90000000/89770000/89761400/89761330/0638e9ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/90000000/89770000/89761400/89761330/fe99a544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Renovated Ski Chalet- Near Blue Mountain Ski! Wasaga Beach [](https://www.expedia.ca/Wasaga-Beach-Hotels-Cozy-Renovated-Ski-Chalet-Near-Blue-Mountain-Ski.h89761330.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/111000000/110240000/110231300/110231283/4c6c1edf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/111000000/110240000/110231300/110231283/616f891d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110240000/110231300/110231283/22d7aa60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110240000/110231300/110231283/3b84d884.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Church Conversion Family Chalet - Pretty River - Collingwood - Blue Mountain Nottawa [](https://www.expedia.ca/Clearview-Hotels-Heritage-Family-Ski-Chalet-Village-Close-To-Collingwood-Blue-Mountain.h110231283.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=2025-12-08&endDate=2025-12-09®ionId=553248635976432418&adults=2&lodging=CHALET&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_553248635976432418) ![](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%2FSimcoe-County-Chalets.d553248635976432418-aaChalets.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSimcoe-County-Chalets.d553248635976432418-aaChalets.Travel-Guide-Accommodation) ## Top Simcoe County Hotel Reviews ![Living Water Resort and Spa](https://images.trvl-media.com/lodging/7000000/6990000/6986300/6986293/02afa7d6_y.jpg) ### Living Water Resort and Spa 10/10 Excellent "Great spa" [](https://expedia.ca/Collingwood-Hotels-Living-Water-Resort-And-Spa.h6986293.Hotel-Information) ![Days Inn by Wyndham Orillia](https://images.trvl-media.com/lodging/1000000/910000/908200/908140/205be5a9_y.jpg) ### Days Inn by Wyndham Orillia 10/10 Excellent "The staff was great. The room was clean. definitely need some work. Carpet in room needs to be replaced curtains in the window. Very filthy. Definitely needs to be replaced." [](https://expedia.ca/Ramara-Hotels-Days-Inn-By-Wyndham-Orillia.h908140.Hotel-Information) ![Comfort Inn & Suites](https://images.trvl-media.com/lodging/1000000/40000/34200/34108/722cfc72_y.jpg) ### Comfort Inn & Suites 10/10 Excellent "Everything" [](https://expedia.ca/Collingwood-Hotels-Comfort-Inn-Suites.h34108.Hotel-Information) ![Days Inn & Suites by Wyndham Collingwood](https://images.trvl-media.com/lodging/2000000/1380000/1374700/1374609/8d176f45_y.jpg) ### Days Inn & Suites by Wyndham Collingwood 10/10 Excellent " Professional friendly staff. Very well located property. Comfortable clean room. Great value for the property." [](https://expedia.ca/Collingwood-Hotels-Days-Inn-Suites-By-Wyndham-Collingwood.h1374609.Hotel-Information) ![Kings Inn Midland](https://images.trvl-media.com/lodging/2000000/1930000/1925600/1925593/a5c93649_y.jpg) ### Kings Inn Midland 10/10 Excellent "I stayed at Kings Inn for a month while visiting family and friends. The owners and staff are great. Check in was easy. All the rooms are walk out with drive up parking at your door. The room was very clean and comfortable. The property is well maintained. Close to all amenities in town. I highly recommend this property to fellow travelers based on friendly staff, cleanliness, location and price. The Kings Inn is my new "must stay" when in Midland, Ontario." [](https://expedia.ca/Midland-Hotels-Kings-Inn-Midland.h1925593.Hotel-Information) ![Holiday Inn Express & Suites Collingwood by IHG](https://images.trvl-media.com/lodging/53000000/52470000/52463900/52463807/10ff1122_y.jpg) ### Holiday Inn Express & Suites Collingwood by IHG 10/10 Excellent "We stayed here as a family of 6 with two kids. Rooms were very clean. Breakfast in morning was very convenient for all. It’s very close to blue mountain village." [](https://expedia.ca/Barrie-Orillia-Hotels-Holiday-Inn-Express-Suites-Collingwood.h52463807.Hotel-Information) ![Carriage Ridge Resort, an Ascend Collection Resort](https://images.trvl-media.com/lodging/2000000/1180000/1177200/1177104/5cd2058c_y.jpg) ### Carriage Ridge Resort, an Ascend Collection Resort 10/10 Excellent "The room was beautiful and romantic room. The staff went above and beyond to ensure our stay was perfect. I will definitely be returning to this place to go to the Vetta Spa that’s right up the street! It’s only a 10 minute walk away! Anyways big big thank you to the staff there for being so winderful. " [](https://expedia.ca/Oro-Medonte-Hotels-Carriage-Ridge-Hills-Resorts.h1177104.Hotel-Information) ![Midland Inn & Suites](https://images.trvl-media.com/lodging/7000000/6580000/6570800/6570799/b2b85c66_y.jpg) ### Midland Inn & Suites 10/10 Excellent "Room was clean and ready for us. Staff was wonderful at check in. Very quick and easy. We always stay here when in town. " [](https://expedia.ca/Midland-Hotels-Midland-Inn-Suites.h6570799.Hotel-Information) ![Candlewood Suites Collingwood by IHG](https://images.trvl-media.com/lodging/100000000/99430000/99424800/99424748/452819e9_y.jpg) ### Candlewood Suites Collingwood by IHG 10/10 Excellent "The room was up to date and spotless. The staff were so pleasant and polite, especially Lorraine" [](https://expedia.ca/Collingwood-Hotels-Candlewood-Suites-Collingwood.h99424748.Hotel-Information) ## Find out more about Simcoe County ## Simcoe County Chalets information | Number of reviews | 10 | | --- | --- | | Accommodation | 15 Chalets | | Lowest Price | | | Highest Price | | ## Explore a world of travel with Expedia - Lodging - Flights - [Apartments in Allandale Waterfront Station](https://www.expedia.ca/Allandale-Waterfront-Station-Apartments.d553248635997307297-aaApartments.Travel-Guide-Accommodation) - [Villas in Allandale Waterfront Station](https://www.expedia.ca/Allandale-Waterfront-Station-Villas.d553248635997307297-aaVillas.Travel-Guide-Accommodation) - [Farmstay in Barrie](https://www.expedia.ca/Barrie-Agritourism.d6692-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Barrie](https://www.expedia.ca/Barrie-Apart-Hotels.d6692-aaApartHotels.Travel-Guide-Accommodation) - [Apartments in Barrie](https://www.expedia.ca/Barrie-Apartments.d6692-aaApartments.Travel-Guide-Accommodation) - 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