Title: Wintergreen Chalets from CA $82 | 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 # Search Chalets in Wintergreen from CA $82 - ![](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 [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-04-10&endDate=2026-04-12&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 ![Outdoor dining](https://images.trvl-media.com/lodging/120000000/119190000/119188100/119188043/d331e7dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, computer monitors](https://images.trvl-media.com/lodging/120000000/119190000/119188100/119188043/4bcd7170.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, computer monitors](https://images.trvl-media.com/lodging/120000000/119190000/119188100/119188043/49b6b501.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/120000000/119190000/119188100/119188043/a4c2aa93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Wintergreen Resort [](https://www.expedia.ca/Roseland-Hotels-Wintergreen-Grandeur.h119188043.Hotel-Information) CA $2,895 CA $4,474 total includes taxes & fees Jan 2 - Jan 3, 2026 [](https://www.expedia.ca/Roseland-Hotels-Wintergreen-Grandeur.h119188043.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/106000000/105500000/105493800/105493762/47de8566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/106000000/105500000/105493800/105493762/w1198h799x0y2-48831f10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/106000000/105500000/105493800/105493762/f7df4dfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/106000000/105500000/105493800/105493762/0d611b59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Afton [](https://www.expedia.ca/Afton-Hotels-Elk-Mountain-Overlook-Breathtaking-Views.h105493762.Hotel-Information) 9.0/10 Wonderful (7) "The location and view (and privacy) were outstanding. The house is cute, easily accommodates 2 people (4 would be ok, but bathroom sharing amongst 4 could be a challenge), and has all of the amenneties to ensure maximimum comfort (blue tooth speaker, decently stocked kitchen, coffee and related items, cute decor, and plenty of towels and hot water." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura CA $412 CA $745 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Afton-Hotels-Elk-Mountain-Overlook-Breathtaking-Views.h105493762.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=2026-01-02&endDate=2026-01-03®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=2026-03-18&d1=2026-03-18&endDate=2026-03-21&d2=2026-03-21&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=2026-03-18&d1=2026-03-18&endDate=2026-03-21&d2=2026-03-21&lodging=VACATION_HOME) 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=2026-03-18&d1=2026-03-18&endDate=2026-03-21&d2=2026-03-21&lodging=APART_HOTEL) 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=2026-03-18&d1=2026-03-18&endDate=2026-03-21&d2=2026-03-21&lodging=APARTMENT) 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=2026-03-18&d1=2026-03-18&endDate=2026-03-21&d2=2026-03-21&lodging=COTTAGE) 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=2026-03-18&d1=2026-03-18&endDate=2026-03-21&d2=2026-03-21&lodging=CONDO) 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=2026-03-18&d1=2026-03-18&endDate=2026-03-21&d2=2026-03-21&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 ![WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS](https://images.trvl-media.com/lodging/49000000/48840000/48830800/48830715/2a174ad4_y.jpg) ### WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS 10/10 Excellent "Wonderful stay! Great communication with the hosts, very clean and comfortable!" [](https://expedia.ca/Charlottesville-Hotels-Wintergreen-Resort-Home-With-Blue-Ridge-Views.h48830715.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 "We absolutely loved this condo, and especially the outstanding views.....a front row seat to gorgeous winter sunrises in your pjs! It was well equipped with everything one needs and was super cozy with a wood burning fireplace to boot. This 2 bedroom was perfect for 2 couples on a birthday weekend....an ideal spot for watching lots of football with beautiful views at every angle in the backdrop. The location is perfect, right across the street from the golf course, seconds from the Wintergarden, and just a few minutes from best sunset spot, Three Ridges Overlook on Devils Knob. We look forward to coming back. Maureen, our host, was wonderful and always available to answer any questions." [](https://expedia.ca/Nellysford-Hotels-Best-Views-On-Mountain-Breathtaking-5-Star-Available-August-26-31-BOOK-NOW.h30501528.Hotel-Information) ![Wintergreen. Sunset Vista Villa - Sea of Mountains](https://images.trvl-media.com/lodging/69000000/68080000/68076800/68076715/3c2ad4b6_y.jpg) ### Wintergreen. Sunset Vista Villa - Sea of Mountains 10/10 Excellent "We love staying at Sunset Vista, especially in December. The condo is clean and has everything we need to enjoy a weekend away. Rebecca and Matt are so helpful, quickly responding to all our questions and needs. Can't wait to go back. This year was extra beautiful with snow! " [](https://expedia.ca/Charlottesville-Hotels-Stunning-Condo-Sunset-Vista-Villa.h68076715.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 "Everything was perfect. Very welcoming, responsive, and clean. " [](https://expedia.ca/Nellysford-Hotels-NEW-Modern-Mountain-Condo-WPool.h77096798.Hotel-Information) ![Stylish-Updated-Central -Walk to Slopes-Dogs OK!](https://images.trvl-media.com/lodging/100000000/99240000/99231000/99230991/b73ebb05_y.jpg) ### Stylish-Updated-Central -Walk to Slopes-Dogs OK! 10/10 Excellent "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." [](https://expedia.ca/Nellysford-Hotels-Stylish-Updated-Central-Walk-To-Slopes-Dogs-OK.h99230991.Hotel-Information) ![Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop](https://images.trvl-media.com/lodging/34000000/33490000/33484800/33484712/31658c2d_y.jpg) ### Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop 10/10 Excellent "Home was well appointed and clean. Host was very helpful and timely in trying to get the TV's working - not being a "streamer", the process was new and frustrating.Enjoyed our stay - second time in this property. " [](https://expedia.ca/Nellysford-Hotels-Wintergreen-Retreat-Bespoke-Luxury-Post-Beam-Home-On-Devils-Knob-Loop.h33484712.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 "Gorgeous view. Our fourth time here, and still a lovely place. " [](https://expedia.ca/Nellysford-Hotels-2br2ba-Million-Dollar-View-From-Luxury-Condo-On-The-Ridge.h27767679.Hotel-Information) ![New Build! Log Cabin with Hot Tub in Wintergreen](https://images.trvl-media.com/lodging/120000000/119320000/119318700/119318633/d3789b54_y.jpg) ### New Build! Log Cabin with Hot Tub in Wintergreen 10/10 Excellent "Perfect place - thank you so much for letting us borrow your home!" [](https://expedia.ca/Nellysford-Hotels-New-Build-Log-Cabin-With-Hot-Tub-In-Wintergreen.h119318633.Hotel-Information) ![Wow! What A View!](https://images.trvl-media.com/lodging/113000000/112620000/112613800/112613786/893db66c_y.jpg) ### Wow! What A View! 10/10 Excellent "Everything was perfect. Loved the view" [](https://expedia.ca/Nellysford-Hotels-Youll-Say-Wow-Over-This-View.h112613786.Hotel-Information) ## Find out more about Wintergreen ## Wintergreen Chalets information | Number of reviews | 15,618 | | ----------------- | ---------- | | Accommodation | 13 Chalets | | Lowest Price | CA $82 | | Highest Price | CA $807 | ## 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) - 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