Title: Wintergreen Condominium Resort Rental from CA $302 | 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 # Find and Compare Wintergreen Condo Resort Rentals - ![](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 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four 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) No exact matches found, but these alternatives could be just right ## Recommended hotels in Wintergreen ![Interior](https://images.trvl-media.com/lodging/69000000/68080000/68076800/68076715/3c2ad4b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68080000/68076800/68076715/79d4e134.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) ### Wintergreen. Sunset Vista Villa - Close to the ski slopes [](https://www.expedia.ca/Charlottesville-Hotels-Stunning-Condo-Sunset-Vista-Villa.h68076715.Hotel-Information) Wintergreen Resort 10/10 Exceptional (92) "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 $161 CA $362 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Charlottesville-Hotels-Stunning-Condo-Sunset-Vista-Villa.h68076715.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) ![Pool](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304212/78b8767e.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) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304212/2c4c7806.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Laurelwood Hollow: Walk to Ski & Swim [](https://www.expedia.ca/Nellysford-Hotels-Laurelwood-Hollow-Walk-To-Ski-Swim.h119304212.Hotel-Information) 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 $131 CA $384 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Nellysford-Hotels-Laurelwood-Hollow-Walk-To-Ski-Swim.h119304212.Hotel-Information) ![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) | 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) | Shared kitchen](https://images.trvl-media.com/lodging/112000000/111090000/111087800/111087718/34db4bb3.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) ### Blackwood Chalet [](https://www.expedia.ca/Nellysford-Hotels-Blackwood-Chalet.h111087718.Hotel-Information) Nellysford 10/10 Exceptional (3) "Love the area" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Toni CA $233 CA $537 total includes taxes & fees Dec 14 - Dec 15 [](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) ![Fireplace](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/29fa29ea.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) ### The Modern Mountain Condo [](https://www.expedia.ca/Nellysford-Hotels-NEW-Modern-Mountain-Condo-WPool.h77096798.Hotel-Information) Wintergreen Resort 10/10 Exceptional (34) "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 $130 CA $319 total includes taxes & fees Dec 14 - Dec 15 [](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) ### Wintergreen Condo -Steps to Ski and restaurants [](https://www.expedia.ca/Nellysford-Hotels-Wintergreen-Condo-Steps-To-Ski-And-Restaurants.h102325315.Hotel-Information) Wintergreen Resort 9.8/10 Exceptional (30) "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 $157 CA $365 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Nellysford-Hotels-Wintergreen-Condo-Steps-To-Ski-And-Restaurants.h102325315.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/44000000/43420000/43414900/43414813/091549e7.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) ![Interior](https://images.trvl-media.com/lodging/44000000/43420000/43414900/43414813/d4f21770.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Escape to the Blue Ridge Mountains at Wine-tergreen! [](https://www.expedia.ca/Bouvet-Island-Hotels-Vrbo-Property.h43414813.Hotel-Information) 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 $148 CA $340 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/Bouvet-Island-Hotels-Vrbo-Property.h43414813.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/110000000/109100000/109092800/109092787/93f9d9bc.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) ![Outdoor dining](https://images.trvl-media.com/lodging/110000000/109100000/109092800/109092787/232bfb44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining [](https://www.expedia.ca/Nellysford-Hotels-Modern-Wintergreen-Retreat-3-Min-From-Slopes.h109092787.Hotel-Information) 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 $186 CA $479 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Nellysford-Hotels-Modern-Wintergreen-Retreat-3-Min-From-Slopes.h109092787.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/96000000/95270000/95269300/95269237/604129c8.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) ![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/f157e73a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course [](https://www.expedia.ca/Nellysford-Hotels-Cozy-1-Bedroom-Condo-Off-12th-Hole-At-Devils-Knob-Golf-Course.h95269237.Hotel-Information) Roseland 9.8/10 Exceptional (21) "Excellent throughout" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) katherine CA $165 CA $342 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Nellysford-Hotels-Cozy-1-Bedroom-Condo-Off-12th-Hole-At-Devils-Knob-Golf-Course.h95269237.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) ![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) ![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) ### Cozy Mountain Retreat \* Dog Friendly [](https://www.expedia.ca/Nellysford-Hotels-Cozy-Mountain-Retreat-Dog-Friendly.h76408075.Hotel-Information) 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) ![Pool](https://images.trvl-media.com/lodging/57000000/56550000/56543700/56543658/a870a931.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) ![Property grounds](https://images.trvl-media.com/lodging/57000000/56550000/56543700/56543658/bc03c18d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly [](https://www.expedia.ca/Charlottesville-Hotels-Pet-Friendly-Wintergreen-Piso-1BD-2BA-Reserva-Ahora-Para-La-Temporada-De-Esqui.h56543658.Hotel-Information) 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 $168 CA $362 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Charlottesville-Hotels-Pet-Friendly-Wintergreen-Piso-1BD-2BA-Reserva-Ahora-Para-La-Temporada-De-Esqui.h56543658.Hotel-Information) ![](https://images.trvl-media.com/lodging/28000000/27770000/27767700/27767679/3ac798a2.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) ![Outdoor dining](https://images.trvl-media.com/lodging/28000000/27770000/27767700/27767679/12a54ff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2br/2ba: Million Dollar View from Luxury Condo on the Ridge. [](https://www.expedia.ca/Nellysford-Hotels-2br2ba-Million-Dollar-View-From-Luxury-Condo-On-The-Ridge.h27767679.Hotel-Information) Roseland 9.0/10 Wonderful (302) "Great view!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Suzanne W. CA $123 CA $302 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) ![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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78460000/78450300/78450238/c029b4b9.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) ### Pine Cottage: Hot Tub, 2 mins to Bold Rock! [](https://www.expedia.ca/Nellysford-Hotels-Pine-Cottage-Hot-Tub-And-Central-To-Nelson-151.h78450238.Hotel-Information) Nellysford 10/10 Exceptional (23) "The house was so nice and clean and the host was great also and we had a great stay and would highly recommend it. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jody W. CA $260 CA $633 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Nellysford-Hotels-Pine-Cottage-Hot-Tub-And-Central-To-Nelson-151.h78450238.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/def44751.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/112000000/111460000/111452000/111451911/7a0dd2b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Design-Lover’s Getaway • Game Room • Hot Tub [](https://www.expedia.ca/Roseland-Hotels-Close-To-The-Slopes-2min-Large-Private-Hot-Tub.h111451911.Hotel-Information) 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 $207 CA $783 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Roseland-Hotels-Close-To-The-Slopes-2min-Large-Private-Hot-Tub.h111451911.Hotel-Information) ![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) ![Interior](https://images.trvl-media.com/lodging/91000000/90130000/90127700/90127668/aabdc1d2.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90130000/90127700/90127668/c8e58b65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly! [](https://www.expedia.ca/Nellysford-Hotels-New-Listing-3-Min-To-Ski-Whot-Tub-And-Fireplace-Dog-Friendly.h90127668.Hotel-Information) Wintergreen Resort 10/10 Exceptional (24) "Amazing place, clean and quiet even though there are houses nearby. Hosts were excellent with communication!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Courtney S. CA $159 CA $463 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Nellysford-Hotels-New-Listing-3-Min-To-Ski-Whot-Tub-And-Fireplace-Dog-Friendly.h90127668.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) ![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/108000000/107860000/107854800/107854723/6989a232.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) ### Bear Tracks Cottage: New Hot Tub + Fire Pit [](https://www.expedia.ca/Nellysford-Hotels-Bear-Tracks-Cottage-NEW-HOT-TUB-FIRE-PIT.h107854723.Hotel-Information) 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 $252 CA $597 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Nellysford-Hotels-Bear-Tracks-Cottage-NEW-HOT-TUB-FIRE-PIT.h107854723.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/113000000/112400000/112394300/112394246/b49906d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/113000000/112400000/112394300/112394246/f29177b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/113000000/112400000/112394300/112394246/800464dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/113000000/112400000/112394300/112394246/0c4a4ab1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### "Glass & Pine" Home close to Bold Rock & Vineyards [](https://www.expedia.ca/Nellysford-Hotels-Glass-Pine-Home-Close-To-Bold-Rock-Vineyards.h112394246.Hotel-Information) Nellysford 10/10 Exceptional (2) "We only stayed one night but wished we could have stayed longer! The place was super clean and the views were beautiful once the rain finally stopped! Close to our favorite brewery and cidery. There were issues with TV reception (buffering) which may just be the area. Not much time for TV watching anyway with all the beautiful things to explore. We enjoyed our stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert H. CA $255 CA $586 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Nellysford-Hotels-Glass-Pine-Home-Close-To-Bold-Rock-Vineyards.h112394246.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/123000000/122840000/122831700/122831616/ef5206ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122840000/122831700/122831616/e60e6023.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122840000/122831700/122831616/10d4b392.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122840000/122831700/122831616/eab7e1aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge [](https://www.expedia.ca/Nellysford-Hotels-First-Floor-Slopeside-Ski-In-Ski-Out-At-Wintergreen.h122831616.Hotel-Information) Wintergreen Resort CA $93 CA $275 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Nellysford-Hotels-First-Floor-Slopeside-Ski-In-Ski-Out-At-Wintergreen.h122831616.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101920000/101916300/101916242/448c50fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/102000000/101920000/101916300/101916242/8c44b91f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, foosball](https://images.trvl-media.com/lodging/102000000/101920000/101916300/101916242/4e7f6a35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101920000/101916300/101916242/b5ed2b2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cabin Ski Retreat • 5 Min to Slopes • Hot Tub • Firepit • Game Room • Hiking [](https://www.expedia.ca/Roseland-Hotels-Wintergreen-Retreat-Cozy-Cabin-With-Hot-Tub.h101916242.Hotel-Information) Chestnut Springs 10/10 Exceptional (15) "Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cheryl P. CA $221 CA $626 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Roseland-Hotels-Wintergreen-Retreat-Cozy-Cabin-With-Hot-Tub.h101916242.Hotel-Information) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/100000000/99240000/99231000/99230991/b73ebb05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/100000000/99240000/99231000/99230991/2887374b.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) ![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) ### Stylish-Updated-Central -Walk to Slopes-Dogs OK! [](https://www.expedia.ca/Nellysford-Hotels-Stylish-Updated-Central-Walk-To-Slopes-Dogs-OK.h99230991.Hotel-Information) Wintergreen Resort 9.8/10 Exceptional (28) "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." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $100 CA $314 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Nellysford-Hotels-Stylish-Updated-Central-Walk-To-Slopes-Dogs-OK.h99230991.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442095/5c8096d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442095/7b8c9b3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, internet, bed sheets](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442095/322fe5dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442095/41c181e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Timbers Studio 46 with Wintergreen Advantage [](https://www.expedia.ca/Nellysford-Hotels-Timbers-Studio-46-With-Wintergreen-Advantage.h102442095.Hotel-Information) Wintergreen 10/10 Exceptional (2) "We only stayed here for a night but it was both relaxing and quiet. The room was very clean and it was spacious for the two of us. It reminded me of a larger hotel room or a studio apartment. You could tell they had put some work into it to make it nice which I appreciated. You have to go to the front desk to check in but it’s not even a 2-minute drive from there. It took us a few minutes to locate it in the dark but that’s just because it’s so dark up there. Great place to stay on a couple... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Madison D. CA $219 CA $368 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Nellysford-Hotels-Timbers-Studio-46-With-Wintergreen-Advantage.h102442095.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=2025-12-27&endDate=2025-12-28®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-Condominium-Resort.d10811-aaCondominiumResort.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWintergreen-Condominium-Resort.d10811-aaCondominiumResort.Travel-Guide-Accommodation) ## Top Wintergreen Hotel Reviews ![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 "Perfect. The condo was exactly like the photos with added holiday touches. Our host, Maureen, was very responsive. The kitchen was well stocked and the view was amazing. " [](https://expedia.ca/Nellysford-Hotels-Best-Views-On-Mountain-Breathtaking-5-Star-Available-August-26-31-BOOK-NOW.h30501528.Hotel-Information) ![You deserve it all! Awesome Views, Comfy Condo & Elevator!](https://images.trvl-media.com/lodging/20000000/19630000/19624500/19624409/86699d42_y.jpg) ### You deserve it all! Awesome Views, Comfy Condo & Elevator! 10/10 Excellent "The views are amazing. The host can also responds promptly if any questions. " [](https://expedia.ca/Charlottesville-Hotels-You-Deserve-It-All-Awesome-Views.h19624409.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 "Perfect stay yet again! " [](https://expedia.ca/Charlottesville-Hotels-Wintergreen-Pet-Friendly-Condo-Wwifi.h29852618.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 "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) ![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) ![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) ![Hiker’s paradise! Come relax this summer!!!](https://images.trvl-media.com/lodging/49000000/48990000/48985600/48985592/1a2a1542_y.jpg) ### Hiker’s paradise! Come relax this summer!!! 10/10 Excellent "The house was comfortable and well maintained. We loved the indoor fireplace" [](https://expedia.ca/Nellysford-Hotels-Hikers-Paradise-Plus-NEW-HOT-TUB.h48985592.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 "I only stayed one night for a EMS class taken at Wintergreen but the place was nice. I only wish I had more days to spend there. The views were fantastic. Everything well maintained. I plan to come back when I have more time to stay. " [](https://expedia.ca/Nellysford-Hotels-2br2ba-Million-Dollar-View-From-Luxury-Condo-On-The-Ridge.h27767679.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) ## Find out more about Wintergreen ## Wintergreen Condo Resorts information | Number of reviews | 870 | | ----------------- | --------------- | | Accommodation | 0 Condo Resorts | | Lowest Price | CA $302 | | Highest Price | CA $783 | ## 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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