Title: Wintergreen Vacation Home Rentals from CA $156: Search Top Private Vacation Homes for Rent | 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 # Wintergreen Vacation 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 [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Apr 17 - Apr 19](https://www.expedia.ca/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) ## Our top choices for Wintergreen vacation homes ![Dining](https://images.trvl-media.com/lodging/113000000/112400000/112394300/112394246/b49906d5.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112400000/112394300/112394246/629cabeb.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) ### "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 $257 CA $595 total includes taxes & fees Jan 13 - Jan 14, 2026 [](https://www.expedia.ca/Nellysford-Hotels-Glass-Pine-Home-Close-To-Bold-Rock-Vineyards.h112394246.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) ![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) ![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) ### 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 $226 CA $552 total includes taxes & fees Jan 13 - Jan 14, 2026 [](https://www.expedia.ca/Nellysford-Hotels-New-Listing-3-Min-To-Ski-Whot-Tub-And-Fireplace-Dog-Friendly.h90127668.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/112000000/112000000/111999900/111999850/14bdbcd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/112000000/112000000/111999900/111999850/d5803f2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/112000000/112000000/111999900/111999850/3e6937f7_edited_3774.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/112000000/111999900/111999850/b49890c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven! [](https://www.expedia.ca/Nellysford-Hotels-Spacious-5-Bedroom-Modern-Home-With-Mountain-Views-Galore-Sauna-EV-Charger.h111999850.Hotel-Information) Nellysford 10/10 Exceptional (4) "We really enjoyed our stay! The home was amazing and very well appointed. We enjoyed local breweries and hiking!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rachel F. CA $410 CA $1,073 total includes taxes & fees Jan 14 - Jan 15, 2026 [](https://www.expedia.ca/Nellysford-Hotels-Spacious-5-Bedroom-Modern-Home-With-Mountain-Views-Galore-Sauna-EV-Charger.h111999850.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) ![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) ![Smart TV, fireplace, video games, foosball](https://images.trvl-media.com/lodging/102000000/101920000/101916300/101916242/52e5512c.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) ### 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 $269 CA $692 total includes taxes & fees Jan 13 - Jan 14, 2026 [](https://www.expedia.ca/Roseland-Hotels-Wintergreen-Retreat-Cozy-Cabin-With-Hot-Tub.h101916242.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/91000000/90930000/90923900/90923831/f5381d94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90930000/90923900/90923831/cbcf5f7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/91000000/90930000/90923900/90923831/0b37c703.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90930000/90923900/90923831/c6b5a028.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful 4-season Mountain Home- New Listing [](https://www.expedia.ca/Nellysford-Hotels-Beautiful-4-Season-Mountain-Home-New-Listing.h90923831.Hotel-Information) Wintergreen Resort 10/10 Exceptional (38) "Great location. Very friendly hosts" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anthony C. CA $272 CA $745 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Nellysford-Hotels-Beautiful-4-Season-Mountain-Home-New-Listing.h90923831.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/97000000/96920000/96920000/96919924/abb60e63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/97000000/96920000/96920000/96919924/9b34431a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96920000/96920000/96919924/5ac8cec0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, offices](https://images.trvl-media.com/lodging/97000000/96920000/96920000/96919924/66b78d58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Adventure Awaits [](https://www.expedia.ca/Roseland-Hotels-3-King-Bdrms.h96919924.Hotel-Information) Laurel Ridge 9.2/10 Wonderful (7) "our stay was so fun! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kaden C. CA $362 CA $767 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Roseland-Hotels-3-King-Bdrms.h96919924.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/78000000/77110000/77100200/77100132/add548d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/78000000/77110000/77100200/77100132/05a5f823.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/78000000/77110000/77100200/77100132/57b1d668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/78000000/77110000/77100200/77100132/w1021h678x3y3-264d8a13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4 BR cabin mins to trails & breweries pets welcome [](https://www.expedia.ca/Nellysford-Hotels-4-BR-Cabin-Mins-To-Trails-Breweries-Pets-Welcome.h77100132.Hotel-Information) Chestnut Springs 9.6/10 Exceptional (28) "Nice place and very clean " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melad K. CA $369 CA $935 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Nellysford-Hotels-4-BR-Cabin-Mins-To-Trails-Breweries-Pets-Welcome.h77100132.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/113000000/112540000/112532200/112532111/6703de10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/113000000/112540000/112532200/112532111/e2360eb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112540000/112532200/112532111/16dadee0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, free WiFi, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/113000000/112540000/112532200/112532111/0197d413.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Distinguished Squirrel Chalet walking distance [](https://www.expedia.ca/Nellysford-Hotels-The-Distinguished-Squirrel-Chalet-Walking-Distance.h112532111.Hotel-Information) Treeloft 9.0/10 Wonderful (8) "we appreciated that it was stocked with basic spices, coffee, necessary cookware, etc. Nice location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ryan R. CA $346 CA $733 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/Nellysford-Hotels-The-Distinguished-Squirrel-Chalet-Walking-Distance.h112532111.Hotel-Information) ![TV, fireplace](https://images.trvl-media.com/lodging/110000000/109800000/109793400/109793345/062975cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/110000000/109800000/109793400/109793345/91c362f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/110000000/109800000/109793400/109793345/b2aff7ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109800000/109793400/109793345/dccda057.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ridge Retreat @ Wintergreen! [](https://www.expedia.ca/Roseland-Hotels-Ridge-Retreat-Wintergreen.h109793345.Hotel-Information) Wintergreen Resort 9.6/10 Exceptional (5) "Beautiful home and it has everything you need for a get-a-way. Five couples and plenty of room to have your own space. Close to lots of recreation and entertainment. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert J. CA $981 CA $1,839 total includes taxes & fees Jan 2 - Jan 3, 2026 [](https://www.expedia.ca/Roseland-Hotels-Ridge-Retreat-Wintergreen.h109793345.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/123000000/122240000/122239400/122239308/0117b5ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/123000000/122240000/122239400/122239308/eeaa863f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/123000000/122240000/122239400/122239308/86646bb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122240000/122239400/122239308/7d61d91c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilltop Hideaway - Wintergreen 5BR with Hot Tub [](https://www.expedia.ca/Nellysford-Hotels-Hilltop-Hideaway-Wintergreen-5BR-With-Hot-Tub.h122239308.Hotel-Information) Wintergreen Resort CA $647 CA $1,398 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Nellysford-Hotels-Hilltop-Hideaway-Wintergreen-5BR-With-Hot-Tub.h122239308.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/119000000/118800000/118792500/118792404/d86d4d61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/119000000/118800000/118792500/118792404/5c655897.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/119000000/118800000/118792500/118792404/fe09c632.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, foosball, books](https://images.trvl-media.com/lodging/119000000/118800000/118792500/118792404/05b23c92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 Mins to Slopes: HotTub, Game room, Family & Pets, 3 King Beds [](https://www.expedia.ca/Nellysford-Hotels-Updated-Mtn-House-2-Mins-To-Resort-3King-Beds.h118792404.Hotel-Information) Laurel Ridge 10/10 Exceptional (3) "We had such a great time, the cabin was great for our friends weekend with perfect sleeping accommodations for a big group. The deck was fantastic for dinner and s’mores bar!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Josh B. CA $659 CA $1,542 total includes taxes & fees Jan 14 - Jan 15, 2026 [](https://www.expedia.ca/Nellysford-Hotels-Updated-Mtn-House-2-Mins-To-Resort-3King-Beds.h118792404.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/96000000/95420000/95414800/95414737/d5a2f074.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95420000/95414800/95414737/92b3705c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, in-room safe, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/96000000/95420000/95414800/95414737/82d1d6dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/96000000/95420000/95414800/95414737/7c259925.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Serene Wintergreen Retreat, Nestled in the Trees [](https://www.expedia.ca/Nellysford-Hotels-Cozy-Mountain-Home-In-Wintergreen-Close-To-Ski-Slopes.h95414737.Hotel-Information) Wintergreen Resort 9.8/10 Exceptional (17) "The property is as wonderful as it looks in the photos. Very close to a beautiful waterfall trail. Definitely would stay here again in a different season to take it all in again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandon D. CA $840 CA $1,551 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Nellysford-Hotels-Cozy-Mountain-Home-In-Wintergreen-Close-To-Ski-Slopes.h95414737.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/108000000/107560000/107557000/107556920/6bcf944f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107560000/107557000/107556920/a0be69dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, foosball](https://images.trvl-media.com/lodging/108000000/107560000/107557000/107556920/d54a8d43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107560000/107557000/107556920/w6720h4478x0y0-424553bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family-Friendly Meets Luxury [](https://www.expedia.ca/Nellysford-Hotels-Family-Friendly-Meets-Luxury.h107556920.Hotel-Information) Pedlars Edge 9.6/10 Exceptional (5) "Great Spot for Family gathering" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ary S. CA $1,077 CA $2,052 total includes taxes & fees Jan 22 - Jan 23, 2026 [](https://www.expedia.ca/Nellysford-Hotels-Family-Friendly-Meets-Luxury.h107556920.Hotel-Information) ![Indoor spa tub](https://images.trvl-media.com/lodging/97000000/96500000/96498900/96498850/31eb2d68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games](https://images.trvl-media.com/lodging/97000000/96500000/96498900/96498850/94a1b12b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96500000/96498900/96498850/a5614347.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96500000/96498900/96498850/dd2eefd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Upscale and Family-Friendly in Wintergreen [](https://www.expedia.ca/Nellysford-Hotels-Upscale-And-Family-Friendly-In-Wintergreen.h96498850.Hotel-Information) Roseland 9.6/10 Exceptional (27) "Well appointed house and property, lots of space, all amenities included. Comms with host were timely and responsive." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tammy G. CA $646 CA $1,363 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Nellysford-Hotels-Upscale-And-Family-Friendly-In-Wintergreen.h96498850.Hotel-Information) ![TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/120000000/119680000/119670100/119670005/15a3512b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119680000/119670100/119670005/ae8bd7d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/120000000/119680000/119670100/119670005/f7ffb901.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/120000000/119680000/119670100/119670005/e6435c53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Trail Magic- Sk-in & Ski-out [](https://www.expedia.ca/Nellysford-Hotels-New-Ski-InSki-Out-At-Wintergreen-Resort-Hot-Tub.h119670005.Hotel-Information) Treeloft CA $1,171 CA $1,942 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Nellysford-Hotels-New-Ski-InSki-Out-At-Wintergreen-Resort-Hot-Tub.h119670005.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/89000000/88370000/88365700/88365665/w905h683x59y0-f89420b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/89000000/88370000/88365700/88365665/w1017h683x4y0-17be165b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/89000000/88370000/88365700/88365665/3502be39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/89000000/88370000/88365700/88365665/a46e7709.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Firefly Springhouse [](https://www.expedia.ca/Staunton-Hotels-The-Firefly-Springhouse.h88365665.Hotel-Information) Staunton 9.8/10 Exceptional (44) "Great cottage for 2 and peaceful setting. Host was helpful with great dinner recommendations " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph CA $113 CA $156 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Staunton-Hotels-The-Firefly-Springhouse.h88365665.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71280000/71271600/71271547/5972c422.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71280000/71271600/71271547/1181496b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/72000000/71280000/71271600/71271547/89e1bc03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71280000/71271600/71271547/202ad8f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Whole House [](https://www.expedia.ca/Amherst-Hotels-Whole-House.h71271547.Hotel-Information) Amherst 9.8/10 Exceptional (33) "The property was just what we wanted -- quiet, private, spacious, comfortable, well equipped. Easy to find and everything worked! We will definitely aim to book this property again when we're back in the area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew CA $123 CA $204 total includes taxes & fees Jan 2 - Jan 3, 2026 [](https://www.expedia.ca/Amherst-Hotels-Whole-House.h71271547.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/72000000/71120000/71112300/71112269/e98a6b9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71120000/71112300/71112269/f8c788a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71120000/71112300/71112269/8c09ec8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/72000000/71120000/71112300/71112269/7c2e5c8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed! [](https://www.expedia.ca/Waynesboro-Hotels-The-Loriann.h71112269.Hotel-Information) Waynesboro 10/10 Exceptional (19) "Beautiful home, very comfortable, and uniquely fun decor. Highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa CA $158 CA $261 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Waynesboro-Hotels-The-Loriann.h71112269.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/84000000/83020000/83010900/83010856/9f1542d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/84000000/83020000/83010900/83010856/4fecfa8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83020000/83010900/83010856/7825e3d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83020000/83010900/83010856/1bbf7f5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hillside Haven: Modern Retreat, Mountain Views [](https://www.expedia.ca/Faber-Hotels-Hillside-Haven-Modern-Retreat.h83010856.Hotel-Information) Faber 10/10 Exceptional (32) "Fantastic property with all the amenities near UVA, and lots of wineries." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) roberto c. CA $245 CA $570 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Faber-Hotels-Hillside-Haven-Modern-Retreat.h83010856.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/77000000/76430000/76424000/76423959/75a06d80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/77000000/76430000/76424000/76423959/67d89f85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/77000000/76430000/76424000/76423959/07a8c718.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![7 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/77000000/76430000/76424000/76423959/763f563a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 5 Bedroom Historic brick home w/ sprawling river views, pool & hot tub! [](https://www.expedia.ca/Waynesboro-Hotels-Charming-5-Bedroom-Historic-Brick-Home-With-Sprawling-River-Views-And-A-POOL.h76423959.Hotel-Information) Waynesboro 10/10 Exceptional (8) "Wonderful day we really enjoyed the pool and hot tub during our stay! This is centrally located and well furnished! The hosts were great with communication!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cameron V. CA $211 CA $655 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Waynesboro-Hotels-Charming-5-Bedroom-Historic-Brick-Home-With-Sprawling-River-Views-And-A-POOL.h76423959.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-08&endDate=2026-01-09®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-Private-Vacation-Homes.d10811-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWintergreen-Private-Vacation-Homes.d10811-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Wintergreen Hotel Reviews ![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 "Very comfortable and quaint! Host was very attentive and responsive. We had a wonderful time " [](https://expedia.ca/Charlottesville-Hotels-Stunning-Condo-Sunset-Vista-Villa.h68076715.Hotel-Information) ![WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS](https://images.trvl-media.com/lodging/49000000/48840000/48830800/48830715/2a174ad4_y.jpg) ### WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS 10/10 Excellent "Such a fun Christmas/mountain vibe! Loved the location and the host was super easy to work with! " [](https://expedia.ca/Charlottesville-Hotels-Wintergreen-Resort-Home-With-Blue-Ridge-Views.h48830715.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 "What a wonderful place. The views breath taking. It was comfortable and clean. Check in easy and very attentive. Highly recommended. " [](https://expedia.ca/Nellysford-Hotels-Breathtaking-Mountain-Views-In-A-2-Bedroom-Condo-At-Wintergreen-Resort.h116728114.Hotel-Information) ![Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026! ](https://images.trvl-media.com/lodging/31000000/30510000/30501600/30501528/922abceb_y.jpg) ### Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026! 10/10 Excellent "We absolutely loved this condo, and especially the outstanding views.....a front row seat to gorgeous winter sunrises in your pjs! It was well equipped with everything one needs and was super cozy with a wood burning fireplace to boot. This 2 bedroom was perfect for 2 couples on a birthday weekend....an ideal spot for watching lots of football with beautiful views at every angle in the backdrop. The location is perfect, right across the street from the golf course, seconds from the Wintergarden, and just a few minutes from best sunset spot, Three Ridges Overlook on Devils Knob. We look forward to coming back. Maureen, our host, was wonderful and always available to answer any questions." [](https://expedia.ca/Nellysford-Hotels-Best-Views-On-Mountain-Breathtaking-5-Star-Available-August-26-31-BOOK-NOW.h30501528.Hotel-Information) ![Upscale and Family-Friendly in Wintergreen](https://images.trvl-media.com/lodging/97000000/96500000/96498900/96498850/31eb2d68_y.jpg) ### Upscale and Family-Friendly in Wintergreen 10/10 Excellent "A beautiful, well-appointed house. The hot tub and sauna were fantastic. We will definitely come back! " [](https://expedia.ca/Nellysford-Hotels-Upscale-And-Family-Friendly-In-Wintergreen.h96498850.Hotel-Information) ![The Modern Mountain Condo ](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/53d40131_y.jpg) ### The Modern Mountain Condo 10/10 Excellent "Everything was perfect. Very welcoming, responsive, and clean. " [](https://expedia.ca/Nellysford-Hotels-NEW-Modern-Mountain-Condo-WPool.h77096798.Hotel-Information) ![Stylish-Updated-Central -Walk to Slopes-Dogs OK!](https://images.trvl-media.com/lodging/100000000/99240000/99231000/99230991/b73ebb05_y.jpg) ### Stylish-Updated-Central -Walk to Slopes-Dogs OK! 10/10 Excellent "This was a great place for our short weekend getaway! We needed a place we could unplug, and that's exactly what we did reading by the fire, but there was plenty to do if we wanted to! We look forward to staying here again." [](https://expedia.ca/Nellysford-Hotels-Stylish-Updated-Central-Walk-To-Slopes-Dogs-OK.h99230991.Hotel-Information) ![2br/2ba: Million Dollar View from Luxury Condo on the Ridge. ](https://images.trvl-media.com/lodging/28000000/27770000/27767700/27767679/3ac798a2_y.jpg) ### 2br/2ba: Million Dollar View from Luxury Condo on the Ridge. 10/10 Excellent "Gorgeous view. Our fourth time here, and still a lovely place. " [](https://expedia.ca/Nellysford-Hotels-2br2ba-Million-Dollar-View-From-Luxury-Condo-On-The-Ridge.h27767679.Hotel-Information) ![New Build! Log Cabin with Hot Tub in Wintergreen](https://images.trvl-media.com/lodging/120000000/119320000/119318700/119318633/d3789b54_y.jpg) ### New Build! Log Cabin with Hot Tub in Wintergreen 10/10 Excellent "Perfect place - thank you so much for letting us borrow your home!" [](https://expedia.ca/Nellysford-Hotels-New-Build-Log-Cabin-With-Hot-Tub-In-Wintergreen.h119318633.Hotel-Information) ## Find out more about Wintergreen ## Wintergreen Vacation Homes information | Number of reviews | 308 | | ----------------- | ------------------ | | Accommodation | 197 Vacation Homes | | Lowest Price | CA $156 | | Highest Price | CA $1,942 | ## 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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