Title: Wintergreen Chalets from CA $324 | 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 $324 - ![](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 [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Wintergreen Chalets No exact matches found, but these alternatives could be just right ## Recommended hotels in Wintergreen ![Terrace/patio](https://images.trvl-media.com/lodging/69000000/68080000/68076800/68076715/48c0e694.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/69000000/68080000/68076800/68076715/3c2ad4b6.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) ![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) ### Condo in Wintergreen Resort 10/10 Exceptional (91) "Beautiful property! Had everything we needed and was very clean! Highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda W. CA $163 CA $372 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Charlottesville-Hotels-Stunning-Condo-Sunset-Vista-Villa.h68076715.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/100000000/99240000/99231000/99230991/2887374b.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) ![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) ### Condo in Wintergreen Resort 9.8/10 Exceptional (27) "Great little place for family to rest after long days of hiking!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) joseph G. CA $102 CA $324 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Nellysford-Hotels-Stylish-Updated-Central-Walk-To-Slopes-Dogs-OK.h99230991.Hotel-Information) ![Cabin, Private Bathroom (Blackwood Chalet) | Exterior](https://images.trvl-media.com/lodging/112000000/111090000/111087800/111087718/f99d2e26.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/a5c8204a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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 in Nellysford 10/10 Exceptional (3) "Love the area" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Toni CA $237 CA $546 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Nellysford-Hotels-Blackwood-Chalet.h111087718.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/53d40131.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/f81462f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/e57932c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/29fa29ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Wintergreen Resort 10/10 Exceptional (33) "Fantastic stay at the Modern Mountain Condo! The check-in process was a breeze, the location is exactly as pictured and was very clean. Spacious location for a couples getaway. Host was extremely responsive to any questions and provided us great instructions and details about the space. Will stay again in the future! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelsey N. CA $140 CA $341 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Nellysford-Hotels-NEW-Modern-Mountain-Condo-WPool.h77096798.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102330000/102325400/102325315/eb46d699.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/103000000/102330000/102325400/102325315/a92ed0cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/103000000/102330000/102325400/102325315/c3acb08c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102330000/102325400/102325315/55159b64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Wintergreen Resort 9.8/10 Exceptional (29) "Had everything we needed, snacks and coffee were great for a cold weekend." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael L. CA $159 CA $370 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Nellysford-Hotels-Wintergreen-Condo-Steps-To-Ski-And-Restaurants.h102325315.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304212/81343878.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304212/w1003h683x0y0-5eec0b74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304212/3c52de65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304212/2c4c7806.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Wintergreen Resort 10/10 Exceptional (2) "We really enjoyed our stay here! Great location, and the condo was very clean and well stocked. Communication with the host was excellent as well. We look forward to returning back some day!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexander H. CA $133 CA $390 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Nellysford-Hotels-Laurelwood-Hollow-Walk-To-Ski-Swim.h119304212.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/44000000/43420000/43414900/43414813/e0ae6d0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/44000000/43420000/43414900/43414813/d4f21770.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/44000000/43420000/43414900/43414813/6fa06431.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/44000000/43420000/43414900/43414813/231c3001.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Wintergreen Resort 9.8/10 Exceptional (123) "The condo was very nice. Located on top of the mountain resort having spectacular views for the outlook just a short walk away. We will be boocking again for our next trip. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $150 CA $345 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Bouvet-Island-Hotels-Vrbo-Property.h43414813.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/110000000/109100000/109092800/109092787/232bfb44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109100000/109092800/109092787/b003bae6.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) ### Condo in Wintergreen Resort 10/10 Exceptional (24) "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 $126 CA $395 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Nellysford-Hotels-Modern-Wintergreen-Retreat-3-Min-From-Slopes.h109092787.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78460000/78450300/78450238/f8a3b378.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, internet](https://images.trvl-media.com/lodging/79000000/78460000/78450300/78450238/abde4226.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/79000000/78460000/78450300/78450238/0a033000.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/79000000/78460000/78450300/78450238/1d0451ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Nellysford 10/10 Exceptional (23) "The house was super cute and accommodated our whole group. It was close to a good amount of breweries and wineries. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Claire B. CA $265 CA $646 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Nellysford-Hotels-Pine-Cottage-Hot-Tub-And-Central-To-Nelson-151.h78450238.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/77000000/76410000/76408100/76408075/3fff194e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76410000/76408100/76408075/d2cb224b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76410000/76408100/76408075/36dcad37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/77000000/76410000/76408100/76408075/26892fb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Guesthouse in Wintergreen Resort 9.6/10 Exceptional (4) "We enjoyed our brief stay at this comfortable property. Liked the decor. Very friendly, responsive host. Would definitely stay again. The mountain scenery in mid-October was spectacular." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Samuel L. [](https://www.expedia.ca/Nellysford-Hotels-Cozy-Mountain-Retreat-Dog-Friendly.h76408075.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/92000000/91340000/91333300/91333207/1c6b26da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/92000000/91340000/91333300/91333207/cc6d8205.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91340000/91333300/91333207/3abeba53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91340000/91333300/91333207/df21f6dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Wintergreen Resort 9.8/10 Exceptional (25) "Love everything about our stay there " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Natalia S. [](https://www.expedia.ca/Nellysford-Hotels-Ready-For-Ski-Season-Book-NOW.h91333207.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/57000000/56550000/56543700/56543658/132f64a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/57000000/56550000/56543700/56543658/bc03c18d.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) ![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) ### Condo in Roseland 9.6/10 Exceptional (142) "Great stay in Wintergreen!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pete K. CA $154 CA $350 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Charlottesville-Hotels-Pet-Friendly-Wintergreen-Piso-1BD-2BA-Reserva-Ahora-Para-La-Temporada-De-Esqui.h56543658.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) ![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/112000000/111460000/111452000/111451911/9fbc2e8d.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) ### Cabin in 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 $210 CA $806 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Roseland-Hotels-Close-To-The-Slopes-2min-Large-Private-Hot-Tub.h111451911.Hotel-Information) ![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) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/28000000/27770000/27767700/27767679/64d05be3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Roseland 9.0/10 Wonderful (301) "Great view!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Suzanne W. CA $138 CA $331 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Nellysford-Hotels-2br2ba-Million-Dollar-View-From-Luxury-Condo-On-The-Ridge.h27767679.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/108000000/107860000/107854800/107854723/8b86069e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/108000000/107860000/107854800/107854723/e7802cf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107860000/107854800/107854723/48027003.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107860000/107854800/107854723/b8f83d57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cabin in Nellysford 10/10 Exceptional (30) "Great location, beautiful home and so much to do nearby." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jordan D. CA $256 CA $610 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Nellysford-Hotels-Bear-Tracks-Cottage-NEW-HOT-TUB-FIRE-PIT.h107854723.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/96000000/95270000/95269300/95269237/e1d8c140.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/96000000/95270000/95269300/95269237/d40343ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/96000000/95270000/95269300/95269237/200109ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95270000/95269300/95269237/604129c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Roseland 9.8/10 Exceptional (21) "Excellent throughout" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) katherine CA $168 CA $347 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Nellysford-Hotels-Cozy-1-Bedroom-Condo-Off-12th-Hole-At-Devils-Knob-Golf-Course.h95269237.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120090000/120087400/120087344/24e460c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120090000/120087400/120087344/0ca17bc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/121000000/120090000/120087400/120087344/5d9cc318.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) ### Condo in Wintergreen Resort 10/10 Exceptional (1) "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 $172 CA $443 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Nellysford-Hotels-Pet-Friendly-3BR3BA-Condo-At-Wintergreen-Resort-Golf-Views-Year-Round-Fun.h120087344.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114160000/114150300/114150295/2c2127ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/115000000/114160000/114150300/114150295/974f0f4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/115000000/114160000/114150300/114150295/bd8e69ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/115000000/114160000/114150300/114150295/cf3b06c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Wintergreen Resort 9.0/10 Wonderful (2) "Property exactly as promised, owner did a great job communicating before the stay.View was perfection, kitchen had two of everything I needed." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) harvey p. CA $168 CA $443 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Nellysford-Hotels-Overlook-180-Degree-Views-WPeloton.h114150295.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718013/6a8171b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718013/b46bd3ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718013/70001ab9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718013/d81b69fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Wintergreen Resort 10/10 Exceptional (26) "Great views" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Arpit N. CA $491 CA $822 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Nellysford-Hotels-Luxury-Condo-In-The-Sky-Finest-In-Wintergreen.h96718013.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/91000000/90130000/90127700/90127668/cc117128.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/91000000/90130000/90127700/90127668/711d6b77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/91000000/90130000/90127700/90127668/c893d39d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90130000/90127700/90127668/aabdc1d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Wintergreen Resort 10/10 Exceptional (24) "A wonderful property to see mountain views and visit the surrounding area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peggy B. CA $165 CA $474 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Nellysford-Hotels-New-Listing-3-Min-To-Ski-Whot-Tub-And-Fireplace-Dog-Friendly.h90127668.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=2025-12-17&endDate=2025-12-18®ionId=10811&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_10811) ## 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=2026-03-03&d1=2026-03-03&endDate=2026-03-06&d2=2026-03-06&lodging=CABIN) 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=2026-03-03&d1=2026-03-03&endDate=2026-03-06&d2=2026-03-06&lodging=CONDO) 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=2026-03-03&d1=2026-03-03&endDate=2026-03-06&d2=2026-03-06&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=2026-03-03&d1=2026-03-03&endDate=2026-03-06&d2=2026-03-06&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=2026-03-03&d1=2026-03-03&endDate=2026-03-06&d2=2026-03-06&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=2026-03-03&d1=2026-03-03&endDate=2026-03-06&d2=2026-03-06&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=2026-03-03&d1=2026-03-03&endDate=2026-03-06&d2=2026-03-06&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 ![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 "Host was welcoming, accommodating, and communicative. The condo was so cute, quant and the perfect size. The view was spectacular and loved waking up to it every morning! Check in and check out was simple and easy. Will definitely come back!" [](https://expedia.ca/Nellysford-Hotels-Breathtaking-Mountain-Views-In-A-2-Bedroom-Condo-At-Wintergreen-Resort.h116728114.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 "Comfortable condo, nice view, easy instructions and clear responsive communication. Seasonal decorations were a nice bonus. We will be returning. " [](https://expedia.ca/Charlottesville-Hotels-Stunning-Condo-Sunset-Vista-Villa.h68076715.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 "Beautiful location. " [](https://expedia.ca/Nellysford-Hotels-Best-Views-On-Mountain-Breathtaking-5-Star-Available-August-26-31-BOOK-NOW.h30501528.Hotel-Information) ![Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining](https://images.trvl-media.com/lodging/110000000/109100000/109092800/109092787/93f9d9bc_y.jpg) ### Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining 10/10 Excellent "The home was clean and in a great location to explore the Wintergreen area. Host was welcoming and responsive." [](https://expedia.ca/Nellysford-Hotels-Modern-Wintergreen-Retreat-3-Min-From-Slopes.h109092787.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 "Wonderful experience! Cozy, clean and comfortable. Beautiful views and great access to hiking! We loved the fireplace and the hot tub, too. Would 10 out of 10 recommend and we plan to return! " [](https://expedia.ca/Nellysford-Hotels-Cozy-Cabin-With-Private-HOT-TUB.h58985753.Hotel-Information) ![Top of Mountain 2 BR Condo, Short Walk to scenic overlooks of the Mtns. in Fall](https://images.trvl-media.com/lodging/68000000/67620000/67610200/67610139/337b5b81_y.jpg) ### Top of Mountain 2 BR Condo, Short Walk to scenic overlooks of the Mtns. in Fall 10/10 Excellent "Very cozy home. Clean and comfortable. Wonderful area for a Fall getaway. " [](https://expedia.ca/Nellysford-Hotels-2-Bedroom-Condo-At-The-Top-Of-The-Mountain.h67610139.Hotel-Information) ![Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes](https://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 place, host thought of everything really" [](https://expedia.ca/Charlottesville-Hotels-Wintergreen-Pet-Friendly-Condo-Wwifi.h29852618.Hotel-Information) ![New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly](https://images.trvl-media.com/lodging/57000000/56550000/56543700/56543658/a870a931_y.jpg) ### New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly 10/10 Excellent "Wonderful place. Cozy, clean, and a lot of thoughtful additions like providing shampoo/conditioner, etc. Would def stay again. " [](https://expedia.ca/Charlottesville-Hotels-Pet-Friendly-Wintergreen-Piso-1BD-2BA-Reserva-Ahora-Para-La-Temporada-De-Esqui.h56543658.Hotel-Information) ![Recently updated - breathtaking view of the Blue Ridge Mountains](https://images.trvl-media.com/lodging/75000000/74880000/74871900/74871843/86d0d842_y.jpg) ### Recently updated - breathtaking view of the Blue Ridge Mountains 10/10 Excellent "We came to enjoy the weather and foliage. We explored some of local favorites and tried new experiences like Crab Tree falls and Belties breakfast on 151. We also discovered some new wine spots. Overall the Ledges provided the best views of our stay and loved our accommodations. We’ll be back in the spring! " [](https://expedia.ca/Nellysford-Hotels-Recently-Updated-Watch-Fireworks-From-The-Deck.h74871843.Hotel-Information) ## Find out more about Wintergreen ## Wintergreen Chalets information | Number of reviews | 892 | | --- | --- | | Accommodation | 13 Chalets | | Lowest Price | CA $324 | | Highest Price | CA $822 | ## 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) - 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