Title: Book the Best Wintergreen Ski Hotels in 2025 from CA $328 | Expedia.ca [Hotels in Wintergreen](https://expedia.ca/Wintergreen-Hotels.d10811.Travel-Guide-Hotels)[Vacation Rentals in Wintergreen](https://expedia.ca/Wintergreen-Vacation-Rentals.d10811.Travel-Guide-VacationRentals)[Things to do in Wintergreen](https://expedia.ca/Things-To-Do-In-Wintergreen.d10811.Travel-Guide-Activities)[Wintergreen Car Rentals](https://expedia.ca/Car-Rentals-In-Wintergreen.d10811.Car-Rental-Guide)[Wintergreen Vacation Packages](https://expedia.ca/Wintergreen.d10811.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/30888d0dcbd6b56a6c3164112bdde6d2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Rebecca Brent # Find Ski Hotels in Wintergreen, VA from CA $328 ![](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 Wintergreen Ski Hotels Tonight [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-10-15&endDate=2025-10-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 16 - Oct 17](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-10-16&endDate=2025-10-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Wintergreen Ski Hotels ![Cabin, Private Bathroom (Blackwood Chalet) | Exterior](https://images.trvl-media.com/lodging/112000000/111090000/111087800/111087718/cb763d2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cabin, Private Bathroom (Blackwood Chalet) | Lounge](https://images.trvl-media.com/lodging/112000000/111090000/111087800/111087718/203c49e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cabin, Private Bathroom (Blackwood Chalet)](https://images.trvl-media.com/lodging/112000000/111090000/111087800/111087718/e6985565.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cabin, Private Bathroom (Blackwood Chalet) | Lounge](https://images.trvl-media.com/lodging/112000000/111090000/111087800/111087718/a5c8204a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blackwood Chalet Nellysford 10/10 Exceptional (3) "Love the area" CA $270 CA $584 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Nellysford-Hotels-Blackwood-Chalet.h111087718.Hotel-Information) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/100000000/99240000/99231000/99230991/b73ebb05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/100000000/99240000/99231000/99230991/43bd17c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99240000/99231000/99230991/ac8a6741.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/100000000/99240000/99231000/99230991/c1b55eb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stylish-Updated-Central -Walk to Slopes-Dogs OK! Wintergreen Resort 9.8/10 Exceptional (25) "Lovely condo. Perfect size for us. Highly recommend, perfect location to go and visit wineries and breweries. Then come back and make a delicious meal or enjoy a beverage on the deck. " CA $105 CA $328 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Nellysford-Hotels-Stylish-Updated-Central-Walk-To-Slopes-Dogs-OK.h99230991.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/110000000/109100000/109092800/109092787/93f9d9bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109100000/109092800/109092787/b003bae6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109100000/109092800/109092787/d176c035.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/110000000/109100000/109092800/109092787/68a8e7c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Retreat @ 3 Ridges / 8 min to Blue Ridge Parkway Wintergreen Resort 10/10 Exceptional (21) "Loved our short stay at the property. Everything was as described. Would stay again." CA $140 CA $431 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Nellysford-Hotels-Modern-Wintergreen-Retreat-3-Min-From-Slopes.h109092787.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/120000000/119240000/119238400/119238386/f2101dda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119240000/119238400/119238386/29dbadf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119240000/119238400/119238386/40009d79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119240000/119238400/119238386/7a98b6f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lofty Pursuits: Spectacular View + EV Charger Treeloft 10/10 Exceptional (3) "Will definitely stay at this location again!!" CA $237 CA $545 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Nellysford-Hotels-Lofty-Pursuits-Spectacular-View-EV-Charger.h119238386.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/112000000/111460000/111452000/111451911/6421312c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/112000000/111460000/111452000/111451911/7a0dd2b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111460000/111452000/111451911/78f359e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111460000/111452000/111451911/9fbc2e8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Design-Lover’s Getaway • Game Room • Hot Tub Wintergreen Resort 9.6/10 Exceptional (4) "We loved our relaxing weekend in the mountains! This was a beautiful house. The house was clean, modern, and stylish. The host went above and beyond to ensure we had a comfortable stay, including checking with us to ensure that we had the Wi-Fi working. We would definitely stay here again!" CA $211 CA $789 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Roseland-Hotels-Close-To-The-Slopes-2min-Large-Private-Hot-Tub.h111451911.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/108000000/107700000/107695300/107695259/e8897717.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107700000/107695300/107695259/b3014a69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107700000/107695300/107695259/110502b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/108000000/107700000/107695300/107695259/a67ce0ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Timbers Lodge 26 with Wintergreen Advantage Wintergreen 10/10 Exceptional (2) "Love staying here! It’s so close to the slope and the staff is great." CA $237 CA $416 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Nellysford-Hotels-Timbers-Lodge-26-With-Wintergreen-Advantage.h107695259.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442095/5c8096d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442095/c1861718.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442095/7b8c9b3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442095/41c181e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Timbers Studio 46 with Wintergreen Advantage Wintergreen 10/10 Exceptional (2) "We only stayed here for a night but it was both relaxing and quiet. The room was very clean and it was spacious for the two of us. It reminded me of a larger hotel room or a studio apartment. You could tell they had put some work into it to make it nice which I appreciated. You have to go to the front desk to check in but it’s not even a 2-minute drive from there. It took us a few minutes to locate it in the dark but that’s just because it’s so dark up there. Great place to stay on a couple... CA $223 CA $378 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Nellysford-Hotels-Timbers-Studio-46-With-Wintergreen-Advantage.h102442095.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/103000000/102450000/102442000/102441969/8268e41a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/103000000/102450000/102442000/102441969/275fe992.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/103000000/102450000/102442000/102441969/f9d207f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/103000000/102450000/102442000/102441969/b35a9159.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain Inn Lodge 78 with Wintergreen Advantage Wintergreen 10/10 Exceptional (2) "Had so much fun! Perfect stay!" CA $237 CA $416 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Nellysford-Hotels-Mountain-Inn-Lodge-78-With-Wintergreen-Advantage.h102441969.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442025/8ed802b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442025/c23d20f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442025/5a21de65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442025/593eaa05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain Inn Studio 96 with Wintergreen Advantage Wintergreen 10/10 Exceptional (1) "A wonderful condo at Wintergreen! It was great to snowboard the whole day and the next day. This was a lovely and clean place to rest. " CA $223 CA $378 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Nellysford-Hotels-Mountain-Inn-Studio-96-With-Wintergreen-Advantage.h102442025.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442005/02bda295.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442005/9f22b636.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442005/2dc42b8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442005/b22c0c25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Timbers Lodge 54 with Wintergreen Advantage Wintergreen 8.0/10 Very good (1) CA $237 CA $416 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Nellysford-Hotels-Timbers-Lodge-54-With-Wintergreen-Advantage.h102442005.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. 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