Title: Book the Best Wintergreen Ski Hotels in 2026 from CA $332 | 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) ![Everything is frozen over at Wintergreen Resort. ](https://images.trvl-media.com/place/553248635996625639/07d79deb-5cfc-4068-8e41-c17e7657b695.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Melissa Smestad # Find Ski Hotels in Wintergreen, VA from CA $332 - ![](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 [Jan 5 - Jan 6](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-01-05&endDate=2026-01-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 6 - Jan 7](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-01-06&endDate=2026-01-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-01-16&endDate=2026-01-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Wintergreen ski hotels ![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) ![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) ![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) ### Stylish-Updated-Central -Walk to Slopes-Dogs OK! [](https://www.expedia.ca/Nellysford-Hotels-Stylish-Updated-Central-Walk-To-Slopes-Dogs-OK.h99230991.Hotel-Information) Wintergreen Resort 9.8/10 Exceptional (30) "This was a great place for our short weekend getaway! We needed a place we could unplug, and that's exactly what we did reading by the fire, but there was plenty to do if we wanted to! We look forward to staying here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $132 CA $358 total includes taxes & fees Jan 6 - Jan 7 [](https://www.expedia.ca/Nellysford-Hotels-Stylish-Updated-Central-Walk-To-Slopes-Dogs-OK.h99230991.Hotel-Information) ![](https://images.trvl-media.com/lodging/28000000/27770000/27767700/27767679/3ac798a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/28000000/27770000/27767700/27767679/12a54ff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/28000000/27770000/27767700/27767679/4641225d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/28000000/27770000/27767700/27767679/26d64274.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2br/2ba: Million Dollar View from Luxury Condo on the Ridge. [](https://www.expedia.ca/Nellysford-Hotels-2br2ba-Million-Dollar-View-From-Luxury-Condo-On-The-Ridge.h27767679.Hotel-Information) Roseland 9.0/10 Wonderful (305) "Outstanding views from the deck!! Loved it!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kerry M. CA $142 CA $332 total includes taxes & fees Jan 6 - Jan 7 [](https://www.expedia.ca/Nellysford-Hotels-2br2ba-Million-Dollar-View-From-Luxury-Condo-On-The-Ridge.h27767679.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/57000000/56550000/56543700/56543658/a870a931.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/57000000/56550000/56543700/56543658/093de133.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/57000000/56550000/56543700/56543658/90-e785bc8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/57000000/56550000/56543700/56543658/cda6931f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly [](https://www.expedia.ca/Charlottesville-Hotels-Pet-Friendly-Wintergreen-Piso-1BD-2BA-Reserva-Ahora-Para-La-Temporada-De-Esqui.h56543658.Hotel-Information) Roseland 9.6/10 Exceptional (143) "Very clean and pet-friendly " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Heston CA $168 CA $361 total includes taxes & fees Jan 6 - Jan 7 [](https://www.expedia.ca/Charlottesville-Hotels-Pet-Friendly-Wintergreen-Piso-1BD-2BA-Reserva-Ahora-Para-La-Temporada-De-Esqui.h56543658.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) ![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) ![Outdoor dining](https://images.trvl-media.com/lodging/110000000/109100000/109092800/109092787/232bfb44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining [](https://www.expedia.ca/Nellysford-Hotels-Modern-Wintergreen-Retreat-3-Min-From-Slopes.h109092787.Hotel-Information) Wintergreen Resort 10/10 Exceptional (26) "The property is extremely clean, well decorated and stocked. We had a fantastic time and absolutely would stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cassie H. CA $155 CA $440 total includes taxes & fees Jan 6 - Jan 7 [](https://www.expedia.ca/Nellysford-Hotels-Modern-Wintergreen-Retreat-3-Min-From-Slopes.h109092787.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/def44751.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Design-Lover’s Getaway • Game Room • Hot Tub [](https://www.expedia.ca/Roseland-Hotels-Close-To-The-Slopes-2min-Large-Private-Hot-Tub.h111451911.Hotel-Information) Wintergreen Resort 9.8/10 Exceptional (6) "Peaceful family trip. The cabin was beautiful, lots of space, and very clean. The cabin had everything we needed. The game room, board games and puzzles were a hit with our kids. Hot tub was huge, clean had its own separate gated area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Victoria R. CA $206 CA $783 total includes taxes & fees Jan 6 - Jan 7 [](https://www.expedia.ca/Roseland-Hotels-Close-To-The-Slopes-2min-Large-Private-Hot-Tub.h111451911.Hotel-Information) ![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)](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) | Shared kitchen](https://images.trvl-media.com/lodging/112000000/111090000/111087800/111087718/34db4bb3.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) ### Blackwood Chalet [](https://www.expedia.ca/Nellysford-Hotels-Blackwood-Chalet.h111087718.Hotel-Information) Nellysford 10/10 Exceptional (3) "Love the area" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Toni CA $290 CA $600 total includes taxes & fees Jan 6 - Jan 7 [](https://www.expedia.ca/Nellysford-Hotels-Blackwood-Chalet.h111087718.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/69000000/68080000/68076800/68076715/3c2ad4b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68080000/68076800/68076715/79d4e134.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68080000/68076800/68076715/319b2ae2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/69000000/68080000/68076800/68076715/b384df8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wintergreen. Sunset Vista Villa - Close to the ski slopes [](https://www.expedia.ca/Charlottesville-Hotels-Stunning-Condo-Sunset-Vista-Villa.h68076715.Hotel-Information) Wintergreen Resort 10/10 Exceptional (95) "Fantastic stay again! Condo is perfect for a get away! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jenna M. CA $229 CA $451 total includes taxes & fees Jan 13 - Jan 14 [](https://www.expedia.ca/Charlottesville-Hotels-Stunning-Condo-Sunset-Vista-Villa.h68076715.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120090000/120087400/120087344/0ca17bc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120090000/120087400/120087344/ae25bee5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120090000/120087400/120087344/a99e93cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120090000/120087400/120087344/ac376d0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 3BR 3BA Pet Friendly Resort Condo [](https://www.expedia.ca/Nellysford-Hotels-Spacious-3BR-3BA-Pet-Friendly-Resort-Condo.h120087344.Hotel-Information) Wintergreen Resort 10/10 Exceptional (3) "Awesome just Awesome place. Definitely recommend this place. Very well taken care of and everything you needed all rolled into one place. Thank you so much again and we will definitely be coming back. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lance B. CA $202 CA $517 total includes taxes & fees Jan 13 - Jan 14 [](https://www.expedia.ca/Nellysford-Hotels-Spacious-3BR-3BA-Pet-Friendly-Resort-Condo.h120087344.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88080000/88074700/88074679/a15eafd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/89000000/88080000/88074700/88074679/7b798769.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/89000000/88080000/88074700/88074679/b6178f6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/89000000/88080000/88074700/88074679/de766882.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious + Serene Mtn Top Escape, 4 En Suites [](https://www.expedia.ca/Nellysford-Hotels-Spacious-Serene-Mtn-Top-Escape.h88074679.Hotel-Information) Wintergreen Resort 10/10 Exceptional (48) "Amazing stay for nelson 151 trip for Birthday. Owners are amazing communication was easy and quick. Property is beautiful and very well maintained. We will be staying here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) DANIEL H. CA $254 CA $669 total includes taxes & fees Jan 7 - Jan 8 [](https://www.expedia.ca/Nellysford-Hotels-Spacious-Serene-Mtn-Top-Escape.h88074679.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90090000/90087300/90087205/b0ffcdf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/91000000/90090000/90087300/90087205/02bbf7d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/91000000/90090000/90087300/90087205/8b8c7238.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90090000/90087300/90087205/89b7b76d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Endless Mountain Top Views from All The Way Up! [](https://www.expedia.ca/Nellysford-Hotels-Endless-Mountain-Top-Views-From-All-The-Way-Up.h90087205.Hotel-Information) Wintergreen Resort 10/10 Exceptional (92) "Perfect location for our weekend stay! Close to trails and breweries and gorgeous views. Responsive hosts, clean and cozy condo. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cari B. CA $167 CA $408 total includes taxes & fees Jan 7 - Jan 8 [](https://www.expedia.ca/Nellysford-Hotels-Endless-Mountain-Top-Views-From-All-The-Way-Up.h90087205.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=2026-01-19&endDate=2026-01-20®ionId=10811&adults=2&location_highlights_explore=ski&sort=RECOMMENDED&openPlayBack=true) ## Top Wintergreen Hotel Reviews ![Amazing Mountain views - Ski In Ski Out - Wifi - fireplace - Pets OK ](https://images.trvl-media.com/lodging/19000000/19000000/18992300/18992227/3c332c07_y.jpg) ### Amazing Mountain views - Ski In Ski Out - Wifi - fireplace - Pets OK 10/10 Excellent "Right on the slope. Had a great ski trip" [](https://expedia.ca/Nellysford-Hotels-Amazing-Mountain-Views-Ski-In-Ski-Out-Wifi-Fireplace-Pets-OK.h18992227.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [2 Star Hotels in Deer Springs ](https://www.expedia.ca/2Star-Deer-Springs-Nellysford-Hotels.s20-n553248635976470298-0.Travel-Guide-Filter-Hotels) - [Apartments in Afton ](https://www.expedia.ca/Afton-Apartments.d6056907-aaApartments.Travel-Guide-Accommodation) - [Cheap Hotels in Afton ](https://www.expedia.ca/Afton-Hotels-Cheap-Hotels.0-0-d6056907-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Bar in Afton ](https://www.expedia.ca/Afton-Hotels-Hotels-With-Bar.0-0-d6056907-tHotelswithBar.Travel-Guide-Filter-Hotels) - [Mountain Hotels in Afton ](https://www.expedia.ca/Afton-Hotels-Mountain-Hotels.0-0-d6056907-tMountainHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Afton ](https://www.expedia.ca/Afton-Hotels-Pet-Friendly-Hotel.0-0-d6056907-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - 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