Title: The Best Wintergreen, VA Chalets from $1,424 | Expedia.com [Wintergreen Travel Guide](https://expedia.com/Wintergreen.dx10811)[Hotels in Wintergreen](https://expedia.com/Wintergreen-Hotels.d10811.Travel-Guide-Hotels)[Vacation Rentals in Wintergreen](https://expedia.com/Wintergreen-Vacation-Rentals.d10811.Travel-Guide-VacationRentals)[Flights to Wintergreen](https://expedia.com/Cheap-Flights-To-Wintergreen.d10811.Travel-Guide-Flights)[Things to do in Wintergreen](https://expedia.com/Things-To-Do-In-Wintergreen.d10811.Travel-Guide-Activities)[Car Rentals in Wintergreen](https://expedia.com/Car-Rentals-In-Wintergreen.d10811.Car-Rental-Guide)[Wintergreen Vacation Packages](https://expedia.com/Wintergreen.d10811.Destination-Travel-Guides) ![](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_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=10811&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 29 - May 31](https://www.expedia.com/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) In three months [Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=10811&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 24 - Jul 26](https://www.expedia.com/Hotel-Search?regionId=10811&startDate=2026-07-24&endDate=2026-07-26&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](https://images.trvl-media.com/lodging/121000000/120770000/120766400/120766318/e8f3a6ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120770000/120766400/120766318/a8d2e498.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, foosball](https://images.trvl-media.com/lodging/121000000/120770000/120766400/120766318/3213c445.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![8 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/121000000/120770000/120766400/120766318/06b597cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fully Loaded 8BR in Wintergreen! Sleeps 23 [](https://www.expedia.com/Nellysford-Hotels-Fully-Loaded-8BR-In-Wintergreen-Sleeps-23.h120766318.Hotel-Information) Chestnut Springs 10/10 Exceptional (10 reviews) "Amazing place with plenty of room for everyone. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph L. $1,379 nightly $1,548 total Apr 8 - Apr 9 Total with taxes and fees [](https://www.expedia.com/Nellysford-Hotels-Fully-Loaded-8BR-In-Wintergreen-Sleeps-23.h120766318.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/124000000/123640000/123630200/123630143/e3f175c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/124000000/123640000/123630200/123630143/5ee47949.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, foosball](https://images.trvl-media.com/lodging/124000000/123640000/123630200/123630143/1131a0dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/124000000/123640000/123630200/123630143/d236365b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Alpenglow- Amazing views, 5 Masters, 5600sf [](https://www.expedia.com/Roseland-Hotels-Alpenglow-Amazing-Views.h123630143.Hotel-Information) Wintergreen Resort 10/10 Exceptional (3 reviews) "Amenities, the extraordinary house itself.,, and the location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Clark H. $1,268 nightly $1,424 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Roseland-Hotels-Alpenglow-Amazing-Views.h123630143.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.com/Hotel-Search?startDate=2026-04-18&endDate=2026-04-19®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.com/Hotel-Search?destination=Wintergreen%2C+Virginia%2C+United+States+of+America®ionId=10811&latLong=37.884861%2C-78.899467&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=CABIN) Cottages [](https://www.expedia.com/Hotel-Search?destination=Wintergreen%2C+Virginia%2C+United+States+of+America®ionId=10811&latLong=37.884861%2C-78.899467&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=COTTAGE) Condos [](https://www.expedia.com/Hotel-Search?destination=Wintergreen%2C+Virginia%2C+United+States+of+America®ionId=10811&latLong=37.884861%2C-78.899467&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=CONDO) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Wintergreen%2C+Virginia%2C+United+States+of+America®ionId=10811&latLong=37.884861%2C-78.899467&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=VACATION_HOME) Chalets [](https://www.expedia.com/Hotel-Search?destination=Wintergreen%2C+Virginia%2C+United+States+of+America®ionId=10811&latLong=37.884861%2C-78.899467&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=CHALET) Apartments [](https://www.expedia.com/Hotel-Search?destination=Wintergreen%2C+Virginia%2C+United+States+of+America®ionId=10811&latLong=37.884861%2C-78.899467&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=APARTMENT) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Wintergreen%2C+Virginia%2C+United+States+of+America®ionId=10811&latLong=37.884861%2C-78.899467&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=APART_HOTEL) ![](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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWintergreen-Chalets.d10811-aaChalets.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWintergreen-Chalets.d10811-aaChalets.Travel-Guide-Accommodation) ## Top Wintergreen Hotel Reviews ![The Modern Mountain Condo ](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/w1273h849x4y3-b64d948a_y.jpg) ### The Modern Mountain Condo 10/10 Excellent "This was an amazing cozy place for the weekend. Everything is near by and easy to get to. The kit hen is well stocked for cooking, and the back porch was lovely to sit on. " [](https://expedia.com/Nellysford-Hotels-NEW-Modern-Mountain-Condo-WPool.h77096798.Hotel-Information) ![Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes](https://images.trvl-media.com/lodging/30000000/29860000/29852700/29852618/6e5f684e_y.jpg) ### Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes 10/10 Excellent "Perfect vacation getaway in the heart of Wintergreen Resort." [](https://expedia.com/Charlottesville-Hotels-Wintergreen-Pet-Friendly-Condo-Wwifi.h29852618.Hotel-Information) ![Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14](https://images.trvl-media.com/lodging/52000000/51800000/51793700/51793663/4496093e_y.jpg) ### Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14 10/10 Excellent "Great home with amazing view of the sunrise." [](https://expedia.com/Nellysford-Hotels-Stunning-Newly-Rebuilt-Home-Perfect-Peaceful-Getaway-That-Sleeps-14.h51793663.Hotel-Information) ![Wintergreen. Sunset Vista Villa - Close to the ski slopes](https://images.trvl-media.com/lodging/69000000/68080000/68076800/68076715/25cf6aa0_y.jpg) ### Wintergreen. Sunset Vista Villa - Close to the ski slopes 10/10 Excellent "My two sisters and I got away to the mountains for a weekend and I'm so glad I found Sunset Vista! The condo was absolutely perfect! It was so well appointed, had a beautiful "large" balcony where we were able to see amazing sunsets. It was clean, the beds were very comfortable and it was so close to local wineries and breweries.Our host, Rebecca was so responsive and accommodating!We can't wait to visit again and no need to look at another property - Sunset Vista is it!" [](https://expedia.com/Charlottesville-Hotels-Stunning-Condo-Sunset-Vista-Villa.h68076715.Hotel-Information) ![Best views on Mountain! Breathtaking 5 Star condo! EASTER STILL AVAILABLE!](https://images.trvl-media.com/lodging/31000000/30510000/30501600/30501528/f17119a4_y.jpg) ### Best views on Mountain! Breathtaking 5 Star condo! EASTER STILL AVAILABLE! 10/10 Excellent "We had a lovely and comfortable stay with beautiful views!" [](https://expedia.com/Nellysford-Hotels-Best-Views-On-Mountain-Breathtaking-5-Star-Available-August-26-31-BOOK-NOW.h30501528.Hotel-Information) ![2br/2ba: Million Dollar View from Luxury Condo on the Ridge. ](https://images.trvl-media.com/lodging/28000000/27770000/27767700/27767679/254bda6d_y.jpg) ### 2br/2ba: Million Dollar View from Luxury Condo on the Ridge. 10/10 Excellent "As advertised, the view was amazing and the sunrise was so beautiful over the mountains. We really enjoyed having a fire on a rainy Monday and being able to go out to lunch without leaving the resort. Really close to the Blue Ridge Parkway and some lovely walks right in the resort. Thanks for a great weekend getaway!" [](https://expedia.com/Nellysford-Hotels-2br2ba-Million-Dollar-View-From-Luxury-Condo-On-The-Ridge.h27767679.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 "Very nice and cozy " [](https://expedia.com/Nellysford-Hotels-Cozy-Cabin-With-Private-HOT-TUB.h58985753.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 "Nice place!" [](https://expedia.com/Nellysford-Hotels-Endless-Mountain-Top-Views-From-All-The-Way-Up.h90087205.Hotel-Information) ![Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort](https://images.trvl-media.com/lodging/117000000/116730000/116728200/116728114/552218fd_y.jpg) ### Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort 10/10 Excellent "The most breathtaking view! Easy communication, clean, and very comfortable. We will definitely be back!" [](https://expedia.com/Nellysford-Hotels-Breathtaking-Mountain-Views-In-A-2-Bedroom-Condo-At-Wintergreen-Resort.h116728114.Hotel-Information) ## Find out more about Wintergreen ## Wintergreen Chalets information | Number of reviews | 13 | | ----------------- | ---------- | | Accommodation | 13 Chalets | | Lowest Price | $1,424 | | Highest Price | $1,548 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Bold Rock Hard Cider Nellysford Cidery ](https://www.expedia.com/Bold-Rock-Hard-Cider-Nellysford-Cidery-Hotels.0-l553248635974658802-0.Travel-Guide-Filter-Hotels) - [Cabin Rentals in Nellysford ](https://www.expedia.com/Nellysford-Cabins.d180913-aaCabins.Travel-Guide-Accommodation) - [B&B in Nellysford ](https://www.expedia.com/Nellysford-Bed-And-Breakfast.d180913-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hotels near Stoney Creek Golf Course ](https://www.expedia.com/Stoney-Creek-Golf-Course-Hotels.0-l553248621587587057-0.Travel-Guide-Filter-Hotels) - 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