Title: Wintergreen Chalets from CA $1,298 | 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 ![](https://images.trvl-media.com/place/553248635996625639/07d79deb-5cfc-4068-8e41-c17e7657b695.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 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Wintergreen chalets ![Exterior detail](https://images.trvl-media.com/lodging/75000000/74490000/74482300/74482204/c66623ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/75000000/74490000/74482300/74482204/4c05e8ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/75000000/74490000/74482300/74482204/0235009b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/75000000/74490000/74482300/74482204/3aee7ec5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Opulent Retreat Amidst Blue Ridge\`s Serenity \* Dog Friendly \* Hot Tub [](https://www.expedia.ca/Nellysford-Hotels-New-Luxury-Mountain-Top-Retreat-WCarriage-House.h74482204.Hotel-Information) Nellysford 10/10 Exceptional (9 reviews) "Just like the pictures, don't hesitate! Just book!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alyssa A. CA $538 CA $1,298 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Nellysford-Hotels-New-Luxury-Mountain-Top-Retreat-WCarriage-House.h74482204.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/105000000/104940000/104935100/104935080/2380fdac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/105000000/104940000/104935100/104935080/ba5b4ab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games](https://images.trvl-media.com/lodging/105000000/104940000/104935100/104935080/e7fe5992.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games](https://images.trvl-media.com/lodging/105000000/104940000/104935100/104935080/f2a4474f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Boutique Chalet - Hiking, Hot Tub, Sauna, Fire Pit, Pizza Oven & Gameroom [](https://www.expedia.ca/Nellysford-Hotels-6BR-Woodland-Retreat-Hot-Tub.h104935080.Hotel-Information) Deer Springs 10/10 Exceptional (8 reviews) "My family and I recently spent a long weekend in August at this family-friendly chalet in Wintergreen and loved every moment. The owners really thought of everything! Highly recommend! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alex d. CA $649 CA $1,447 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Nellysford-Hotels-6BR-Woodland-Retreat-Hot-Tub.h104935080.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=2026-02-21&endDate=2026-02-22®ionId=10811&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=Wintergreen%2C+Virginia%2C+United+States+of+America®ionId=10811&latLong=37.884861%2C-78.899467&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=CABIN) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Wintergreen%2C+Virginia%2C+United+States+of+America®ionId=10811&latLong=37.884861%2C-78.899467&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=VACATION_HOME) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Wintergreen%2C+Virginia%2C+United+States+of+America®ionId=10811&latLong=37.884861%2C-78.899467&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=COTTAGE) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Wintergreen%2C+Virginia%2C+United+States+of+America®ionId=10811&latLong=37.884861%2C-78.899467&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=APART_HOTEL) Condos [](https://www.expedia.ca/Hotel-Search?destination=Wintergreen%2C+Virginia%2C+United+States+of+America®ionId=10811&latLong=37.884861%2C-78.899467&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=CONDO) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Wintergreen%2C+Virginia%2C+United+States+of+America®ionId=10811&latLong=37.884861%2C-78.899467&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=APARTMENT) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Wintergreen%2C+Virginia%2C+United+States+of+America®ionId=10811&latLong=37.884861%2C-78.899467&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=CHALET) ![](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%2FWintergreen-Chalets.d10811-aaChalets.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWintergreen-Chalets.d10811-aaChalets.Travel-Guide-Accommodation) ## Top Wintergreen Hotel Reviews ![Serenity Cabin-Woodland Retreat](https://images.trvl-media.com/lodging/110000000/109550000/109542600/109542556/5164314f_y.jpg) ### Serenity Cabin-Woodland Retreat 10/10 Excellent "Wonderful stay with great communication with the host " [](https://expedia.ca/Nellysford-Hotels-Serenity-Cabin-3-Bedroom-Woodland-Retreat-In-Wintergreen.h109542556.Hotel-Information) ![Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026! ](https://images.trvl-media.com/lodging/31000000/30510000/30501600/30501528/922abceb_y.jpg) ### Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026! 10/10 Excellent "What an amazing home! Just incredible views from the floor to ceiling windows. We loved everything about this home. Beds were very comfortable. Plenty of room for us 4 adults. The host, Maureen, was very helpful and quick to respond with any questions we had. I would definitely book here again. We had such a relaxing stay. " [](https://expedia.ca/Nellysford-Hotels-Best-Views-On-Mountain-Breathtaking-5-Star-Available-August-26-31-BOOK-NOW.h30501528.Hotel-Information) ![The Modern Mountain Condo ](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/53d40131_y.jpg) ### The Modern Mountain Condo 10/10 Excellent "Excellent location, walked right over to the top of the slopes and about 30 yards from the market. Everything was clean, in good working order and perfect for our party of three" [](https://expedia.ca/Nellysford-Hotels-NEW-Modern-Mountain-Condo-WPool.h77096798.Hotel-Information) ![Dobie condo, renovated top to bottom! LOTS OF DETAILED INFO LISTED ☺️](https://images.trvl-media.com/lodging/41000000/40900000/40894200/40894108/228cd4e3_y.jpg) ### Dobie condo, renovated top to bottom! LOTS OF DETAILED INFO LISTED ☺️ 10/10 Excellent "Always enjoy the staying here!!" [](https://expedia.ca/Charlottesville-Hotels-New-To-The-Market.h40894108.Hotel-Information) ![Endless Mountain Top Views from All The Way Up!](https://images.trvl-media.com/lodging/91000000/90090000/90087300/90087205/b0ffcdf7_y.jpg) ### Endless Mountain Top Views from All The Way Up! 10/10 Excellent "The VIEWS!!!!!!!! WOW! Absolutely stunning!Sunrises, mountain vistas, slopes and skiers!Beautiful home! Well appointed with everything you could need!Best location! Wonderfully attentive hosts!We will be back!Thank you!" [](https://expedia.ca/Nellysford-Hotels-Endless-Mountain-Top-Views-From-All-The-Way-Up.h90087205.Hotel-Information) ![2br/2ba: Million Dollar View from Luxury Condo on the Ridge. ](https://images.trvl-media.com/lodging/28000000/27770000/27767700/27767679/3ac798a2_y.jpg) ### 2br/2ba: Million Dollar View from Luxury Condo on the Ridge. 10/10 Excellent "This is one of our favorite condos in Wintergreen. Spacious, clean, the deck is just great for relaxing and enjoying the view . " [](https://expedia.ca/Nellysford-Hotels-2br2ba-Million-Dollar-View-From-Luxury-Condo-On-The-Ridge.h27767679.Hotel-Information) ![Panoramic Peak: Wintergreen Condo with Views](https://images.trvl-media.com/lodging/91000000/90240000/90233100/90233005/c2978783_y.jpg) ### Panoramic Peak: Wintergreen Condo with Views 10/10 Excellent "Highly Recommend " [](https://expedia.ca/Nellysford-Hotels-Panoramic-Peak-Wintergreen-Condo-With-Views.h90233005.Hotel-Information) ![Cozy Cabin with private HOT TUB!](https://images.trvl-media.com/lodging/59000000/58990000/58985800/58985753/90-636eaa8c_y.jpg) ### Cozy Cabin with private HOT TUB! 10/10 Excellent "We enjoyed our visit. Beautiful cabin, very quiet and peaceful." [](https://expedia.ca/Nellysford-Hotels-Cozy-Cabin-With-Private-HOT-TUB.h58985753.Hotel-Information) ![Insane Mountain Views - New Listing](https://images.trvl-media.com/lodging/94000000/93350000/93341800/93341768/2e9f0ebe_y.jpg) ### Insane Mountain Views - New Listing 10/10 Excellent "Amazing home. We had such a wonderful time with our family! The view and sunrises are unforgettable! Kitchen size is perfect with double fridges and ice machine. Loved having holiday music throughout the home. Can’t wait to book again!" [](https://expedia.ca/Roseland-Hotels-Insane-Mountain-Views-New-Listing.h93341768.Hotel-Information) ## Find out more about Wintergreen ## Wintergreen Chalets information | Number of reviews | 7 | | ----------------- | ---------- | | Accommodation | 13 Chalets | | Lowest Price | CA $1,298 | | Highest Price | CA $1,447 | ## 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) - [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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