Title: Wintergreen Chalets from CA $376 | 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 # Search Chalets in Wintergreen from CA $376 ![](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 Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-10-17&endDate=2025-10-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Wintergreen Chalets ![Outdoor spa tub](https://images.trvl-media.com/lodging/63000000/62620000/62612000/62611923/dfad674a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, foosball, stereo](https://images.trvl-media.com/lodging/63000000/62620000/62612000/62611923/46538bcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/63000000/62620000/62612000/62611923/f2b6b704.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, foosball, stereo](https://images.trvl-media.com/lodging/63000000/62620000/62612000/62611923/ffba14b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Chalet, Best Views in Virginia Wintergreen Resort 9.8/10 Exceptional (30) "Great house, great owner, incredible views. As good as it gets in the entire mid-Atlantic" CA $1,208 CA $2,303 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Nellysford-Hotels-Luxury-Chalet.h62611923.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/113000000/112230000/112220700/112220612/0e8c49ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, video library](https://images.trvl-media.com/lodging/113000000/112230000/112220700/112220612/3055e254.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, video library](https://images.trvl-media.com/lodging/113000000/112230000/112220700/112220612/ef7acd02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112230000/112220700/112220612/274f11db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lotus View Retreat in Yogaville, Chalet with WiFi and AC Buckingham 10/10 Exceptional (6) "We loved our quick stay. Check in and check out were very low-key, easy, and flexible. The cabin was immaculate and well appointed with everything we could need. " CA $222 CA $376 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Buckingham-Hotels-Lotus-View-Retreat-In-Yogaville.h112220612.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/109000000/108920000/108916800/108916763/30daf106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books, offices](https://images.trvl-media.com/lodging/109000000/108920000/108916800/108916763/a1d8182f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108920000/108916800/108916763/f4ae5de9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/109000000/108920000/108916800/108916763/8cd1be48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wintergreen Ridge Retreat Chestnut Springs 9.0/10 Wonderful (4) "Enjoyed our stay, the property was very nice, communicated with property manager regarding a few issues and they were responsive. Accommodated the number of guests we had. Could use a bigger parking area for amount of guests that could be accommodated. " CA $378 CA $801 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Roseland-Hotels-New-Hot-Tub-Wintergreen-Resort-Ski-Spa.h108916763.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) ![Dining](https://images.trvl-media.com/lodging/106000000/105500000/105493800/105493762/f7df4dfd.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) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/106000000/105500000/105493800/105493762/c682f7ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Elk Mountain Overlook: Breathtaking Views Afton 6.0/10 (2) "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." CA $431 CA $772 total includes taxes & fees Oct 19 - Oct 20 [](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=2025-10-26&endDate=2025-10-27®ionId=10811&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](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 Pet-Friendly Condo: Walk to Mountain Inn & Slopes](//images.trvl-media.com/lodging/30000000/29860000/29852700/29852618/f4cdee3d_y.jpg) ### Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes 10/10 Excellent "Comfortable clean and quiet place to stay during the beginning of October." [](https://expedia.ca/Charlottesville-Hotels-Wintergreen-Pet-Friendly-Condo-Wwifi.h29852618.Hotel-Information) ![Holiday Inn Express & Suites Waynesboro East by IHG](//images.trvl-media.com/lodging/97000000/96550000/96546000/96545978/22c5f5c1_y.jpg) ### Holiday Inn Express & Suites Waynesboro East by IHG 10/10 Excellent "Everything was top notch " [](https://expedia.ca/Waynesboro-Hotels-Holiday-Inn-Express-And-Suites-Waynesboro-East.h96545978.Hotel-Information) ![Sleep Inn Staunton](//images.trvl-media.com/lodging/1000000/170000/168400/168389/f334eca9_y.jpg) ### Sleep Inn Staunton 10/10 Excellent "Shower stall was too small, one bed squeaked and creaked, breakfast food and coffee weren’t hot, breakfast food wasn’t refilled, no place to sit in the room other than the bed or one desk chair." [](https://expedia.ca/Staunton-Hotels-Sleep-Inn-Staunton.h168389.Hotel-Information) ![Motel 6 Staunton, VA](//images.trvl-media.com/lodging/1000000/10000/9000/8977/e2fd1c0e_y.jpg) ### Motel 6 Staunton, VA 10/10 Excellent "The room was very clean, fast check in, the bed wasn't super comfortable but for less expensive lodging it was completely acceptable. I was impressed." [](https://expedia.ca/Staunton-Hotels-Motel-6-Staunton.h8977.Hotel-Information) ![Comfort Inn](//images.trvl-media.com/lodging/1000000/70000/64100/64084/2a69aac3_y.jpg) ### Comfort Inn 10/10 Excellent "Was very clean" [](https://expedia.ca/Staunton-Hotels-Comfort-Inn.h64084.Hotel-Information) ![Holiday Inn Express & Suites Staunton by IHG](//images.trvl-media.com/lodging/47000000/46550000/46550000/46549911/8e95e8a0_y.jpg) ### Holiday Inn Express & Suites Staunton by IHG 10/10 Excellent "Reception was fantastic." [](https://expedia.ca/Staunton-Hotels-Holiday-Inn-Express-And-Suites-Staunton.h46549911.Hotel-Information) ![Hotel 24 South](//images.trvl-media.com/lodging/2000000/1320000/1311400/1311324/76d25ca1_y.jpg) ### Hotel 24 South 10/10 Excellent "Terrific location. The room was very clean and comfortable. " [](https://expedia.ca/Staunton-Hotels-Hotel-24-South.h1311324.Hotel-Information) ![Holiday Inn Staunton Conference Center by IHG](//images.trvl-media.com/lodging/1000000/20000/19200/19125/c184cf6d_y.jpg) ### Holiday Inn Staunton Conference Center by IHG 10/10 Excellent "Very ckean" [](https://expedia.ca/Staunton-Hotels-Holiday-Inn-Staunton-Conference-Center.h19125.Hotel-Information) ![Quality Inn Waynesboro - Skyline Drive](//images.trvl-media.com/lodging/1000000/30000/22300/22261/dedaf9e2_y.jpg) ### Quality Inn Waynesboro - Skyline Drive 10/10 Excellent "The staff were very helpful and friendly. They provided recommendations for local attractions and events. Rooms were quite and clean and the beds were comfortable. Breakfast was adequate. Check in and check out was quick and easy. Staff were very responsive to a room maintenance need. Would recommend and will stay there again." [](https://expedia.ca/Staunton-Hotels-Quality-Inn-Waynesboro.h22261.Hotel-Information) ## Find out more about Wintergreen ## Wintergreen Chalets information | Number of reviews | 38 | | --- | --- | | Accommodation | 15 Chalets | | Lowest Price | CA $376 | | Highest Price | CA $2,303 | ## 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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[Flights from Faber](https://www.expedia.ca/lp/flights/6353692/flights-from-faber) - [Visit Blue Ridge Tunnel Trail](https://www.expedia.ca/Blue-Ridge-Tunnel-Trail.dx847217400490500096) - [Lovingston Winery](https://www.expedia.ca/Lovingston-Winery-Lovingston.d553248621532658155.Vacation-Attraction) - [Rockfish Gap Entrance Shenandoah](https://www.expedia.ca/Rockfish-Gap-Entrance-Shenandoah-Waynesboro.d6129965.Vacation-Attraction) - [Visit Roseland](https://www.expedia.ca/Roseland.dx6361484) - [Visit Tyro](https://www.expedia.ca/Tyro.dx3000460704) - [Visit Waynesboro](https://www.expedia.ca/Waynesboro.dx6733) - [Car rental Afton](https://www.expedia.ca/Car-Rentals-In-Afton.d6056907.Car-Rental-Guide) - [Car rental Tyro](https://www.expedia.ca/Car-Rentals-In-Tyro.d3000460704.Car-Rental-Guide) - [Car rentals near Veritas Vineyard and Winery](https://www.expedia.ca/Car-Rentals-In-Veritas-Vineyard-And-Winery.d6093181.Car-Rental-Guide) - [Car rentals near Wintergreen Resort](https://www.expedia.ca/Car-Rentals-In-Wintergreen-Resort.d6093285.Car-Rental-Guide) - [Enterprise Rental Cars in Blue Ridge Tunnel Trail](https://www.expedia.ca/Enterprise-Car-Rentals-In-Blue-Ridge-Tunnel-Trail.d847217400490500096-c15.Car-Rental-Guide-Suppliers) - [Hertz Rental Cars in Blue Ridge Tunnel Trail](https://www.expedia.ca/Hertz-Car-Rentals-In-Blue-Ridge-Tunnel-Trail.d847217400490500096-c40.Car-Rental-Guide-Suppliers) - [Premium Car Rentals in Blue Ridge Tunnel Trail](https://www.expedia.ca/Premium-Car-Rentals-In-Blue-Ridge-Tunnel-Trail.d847217400490500096-tPremium.Car-Rental-Guide-Class) - [Things to do in Roseland](https://www.expedia.ca/Things-To-Do-In-Roseland.d6361484.Travel-Guide-Activities) - [Things to do in Waynesboro](https://www.expedia.ca/Things-To-Do-In-Waynesboro.d6733.Travel-Guide-Activities) - [Book Chalets in Wintergreen on Expedia.com](https://www.expedia.com/Wintergreen-Chalets.d10811-aaChalets.Travel-Guide-Accommodation)