Title: Wintergreen Vacation Home Rentals from CA $160: 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) ![](https://mediaim.expedia.com/destination/2/30888d0dcbd6b56a6c3164112bdde6d2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Rebecca Brent # 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 Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Wintergreen Vacation Homes ![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) ![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) ![Exterior](https://images.trvl-media.com/lodging/91000000/90130000/90127700/90127668/cc117128.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy chalet w/ king beds, fireplace, and hot tub. Dog-friendly! Close to hiking. 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 $151 CA $462 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Nellysford-Hotels-New-Listing-3-Min-To-Ski-Whot-Tub-And-Fireplace-Dog-Friendly.h90127668.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) ![TV, fireplace, offices](https://images.trvl-media.com/lodging/113000000/112540000/112532200/112532111/3eb2493c.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) ![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) ### The Distinguished Squirrel Chalet walking distance Treeloft 9.8/10 Exceptional (7) "Love the layout, how it was decorated, beds were nice, and every little detail was thought of!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laurie S. CA $272 CA $620 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Nellysford-Hotels-The-Distinguished-Squirrel-Chalet-Walking-Distance.h112532111.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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/112000000/112000000/111999900/111999850/d5803f2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven! 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 $418 CA $1,095 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Nellysford-Hotels-Spacious-5-Bedroom-Modern-Home-With-Mountain-Views-Galore-Sauna-EV-Charger.h111999850.Hotel-Information) ![House](https://images.trvl-media.com/lodging/121000000/120110000/120102000/120101948/d4b66a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/121000000/120110000/120102000/120101948/8c76c84d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/121000000/120110000/120102000/120101948/dba9787a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/121000000/120110000/120102000/120101948/8ca22e8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wintergreen Ridge Retreat - Family Home Pedlars Edge [](https://www.expedia.ca/Nellysford-Hotels-Wintergreen-Ridge-Retreat-Family-Home.h120101948.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) ![Exterior](https://images.trvl-media.com/lodging/72000000/71120000/71112300/71112269/8c09ec8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71120000/71112300/71112269/921c0c9d.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) ### The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed! 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 $99 CA $196 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Waynesboro-Hotels-The-Loriann.h71112269.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) ![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) ![Interior](https://images.trvl-media.com/lodging/72000000/71280000/71271600/71271547/34f30416.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Whole House Amherst 9.6/10 Exceptional (30) "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 $110 CA $229 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Amherst-Hotels-Whole-House.h71271547.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) ![Interior](https://images.trvl-media.com/lodging/77000000/76430000/76424000/76423959/f7c74f68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 5 Bedroom Historic brick home w/ sprawling river views, pool & hot tub! Waynesboro 10/10 Exceptional (7) "We really enjoyed our stay at the property! With so many rooms, there was space for everyone, and everything was very clean upon our arrival. The hot tub was perfect for a cold night! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephen S. CA $215 CA $708 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Waynesboro-Hotels-Charming-5-Bedroom-Historic-Brick-Home-With-Sprawling-River-Views-And-A-POOL.h76423959.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/89000000/88370000/88369700/88369669/881cb7a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/89000000/88370000/88369700/88369669/76c7dd21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books](https://images.trvl-media.com/lodging/89000000/88370000/88369700/88369669/1a8b755b.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/89000000/88370000/88369700/88369669/fd8f2ce4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Bungalow 30 minutes from Wintergreen Roseland 10/10 Exceptional (14) "Great stay! Thank you!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lauren CA $133 CA $345 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Roseland-Hotels-Historic-Bungalow-30-Minutes-From-Wintergreen.h88369669.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112560000/112550100/112550097/fde6c4b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/113000000/112560000/112550100/112550097/18804839.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112560000/112550100/112550097/dfb9c79e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/113000000/112560000/112550100/112550097/958e13db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hot Tub | Fire Pit | River | State Park | King Bed Wingina 10/10 Exceptional (4) "Hygge House was very clean and a refreshing stay! Hot tub was relaxing. Overall, a beautiful and restful retreat. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Candy H. CA $148 CA $411 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Wingina-Hotels-Hot-Tub-Fire-Pit-River-State-Park-King-Bed.h112550097.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) ![Property grounds](https://images.trvl-media.com/lodging/89000000/88370000/88365700/88365665/3502be39.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) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/89000000/88370000/88365700/88365665/8b35497e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Firefly Springhouse Staunton 9.8/10 Exceptional (40) "Lovely spot with friendly hosts. Comfortable bed, bath and we enjoyed viewing the animals from the porch while sipping coffee. We hope to be back again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carol H. CA $115 CA $160 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Staunton-Hotels-The-Firefly-Springhouse.h88365665.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) ![Interior](https://images.trvl-media.com/lodging/84000000/83020000/83010900/83010856/1bbf7f5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/84000000/83020000/83010900/83010856/2c0e912e.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) ### Hillside Haven: Modern Retreat, Mountain Views Faber 10/10 Exceptional (30) "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 $250 CA $589 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Faber-Hotels-Hillside-Haven-Modern-Retreat.h83010856.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87140000/87135400/87135309/f284b725.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/88000000/87140000/87135400/87135309/34f346a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/88000000/87140000/87135400/87135309/32047678.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/88000000/87140000/87135400/87135309/6e857d99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Hawksbill Haus (w/ hot tub) Waynesboro 9.6/10 Exceptional (8) "Home was as described. Location was close enough to stores and attractions. Hot tub was nice." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Catherine D. CA $149 CA $455 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Waynesboro-Hotels-The-Hawksbill-Haus.h87135309.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/79000000/78650000/78647300/78647228/45a45c09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78650000/78647300/78647228/7534c2d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/79000000/78650000/78647300/78647228/620df162.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78650000/78647300/78647228/2f52c4ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW! Cheerful 2 bd bungalow with hot tub. Must see! Waynesboro 9.6/10 Exceptional (44) "We enjoyed this cozy home during our annual trip to the area. Loved the charming, private backyard. Nearby vineyards and Blue Ridge Parkway were an added bonus. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Virginia W. CA $163 CA $287 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Waynesboro-Hotels-NEW-Cheerful-2-Bd-Bungalow-With-Hot-Tub-Must-See.h78647228.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90240000/90233000/90232991/15dbdf18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90240000/90233000/90232991/bc6d36f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/91000000/90240000/90233000/90232991/3faf6275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/91000000/90240000/90233000/90232991/ba298821.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Green on New - Central Location and Staunton Charm Staunton 9.4/10 Exceptional (12) "Really enjoyed our stay! Very clean and quaint little place. Would stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JANIE M. CA $152 CA $353 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Staunton-Hotels-Green-On-New-Central-Location-And-Staunton-Charm.h90232991.Hotel-Information) ![Smart TV, DVD player](https://images.trvl-media.com/lodging/93000000/92890000/92883900/92883873/w505h683x260y0-05167a1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92890000/92883900/92883873/w906h683x59y0-96d4c6f2.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/93000000/92890000/92883900/92883873/w505h683x260y0-19330ce9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/93000000/92890000/92883900/92883873/w906h683x59y0-b340732b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Country small two bedroom home. Roseland 9.8/10 Exceptional (17) "Lovely cozy place in the mountains, we had a total blast!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Prabir CA $188 CA $345 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Roseland-Hotels-Cozy-Country-Small-Two-Bedroom-Home.h92883873.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/104000000/103710000/103700200/103700145/w1500h999x0y1-af80a03d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/104000000/103710000/103700200/103700145/8f7529ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103710000/103700200/103700145/ac85deba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/104000000/103710000/103700200/103700145/ce1ba570.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Little Yellow House: Walk to Downtown Staunton Staunton 10/10 Exceptional (6) "I loved the location and the extra amenities !" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Miriam CA $138 CA $398 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Staunton-Hotels-Little-Yellow-House-Walk-To-Downtown-Staunton.h103700145.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/98000000/97570000/97567300/97567212/96f88f22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/98000000/97570000/97567300/97567212/514e415f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97570000/97567300/97567212/1282194d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/98000000/97570000/97567300/97567212/8bbb4705.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Craftsman: Newly Renovated/Downtown Staunton Staunton 9.8/10 Exceptional (26) "Perfect home base to our Girl Trip. Thank you for sharing your home. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cindy M. CA $194 CA $487 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Cozy-Craftsman-Newly-Renovateddowntown-Staunton.h97567212.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/91000000/90240000/90233000/90232989/w2881h1923x0y0-c1a362b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90240000/90233000/90232989/5abbc56b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/91000000/90240000/90233000/90232989/1fae8fdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/91000000/90240000/90233000/90232989/15c61154.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fox Hill: 151 Cottage w/Hot Tub + Mountain Views Afton 10/10 Exceptional (13) "We had a wonderful stay! The long driveway made us feel tucked away in a forest. The home has an open floor plan on the first floor giving it a great feel. Beds were comfortable. We enjoyed the visit." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marisa R. CA $319 CA $714 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Afton-Hotels-NEW-Fox-Hill-151-Cottage-Hot-Tub.h90232989.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/91000000/90240000/90233100/90233022/2219cb82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90240000/90233100/90233022/f39f4bf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/91000000/90240000/90233100/90233022/a863a6d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/91000000/90240000/90233100/90233022/c2f4237e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Hunker Down: Cheerful 2 Bed and Pet Friendly Staunton 9.0/10 Wonderful (13) "We stayed here with our two kids (age 2 and 3) and would stay again! The apartment was incredibly clean with plenty of space and everything we needed. We sleep with white noise machines and had no issues with noise at all. Check in and parking was easy and the hosts were very responsive. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle S. CA $160 CA $348 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Staunton-Hotels-The-Hunker-Down-Cheerful-2-Bed-And-Pet-Friendly.h90233022.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/108000000/107020000/107020000/107019915/d2e674f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107020000/107020000/107019915/a82e2e03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/108000000/107020000/107020000/107019915/3abf3933.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/108000000/107020000/107020000/107019915/63098aac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tucked Inn: Lower Unit - NEW Nelson Co Getaway Nellysford CA $139 CA $407 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Nellysford-Hotels-Tucked-Inn-Lower-Unit-NEW-Nelson-Co-Getaway.h107019915.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=2025-11-13&endDate=2025-11-14®ionId=10811&adults=2&lodging=VACATION_HOME&sort=RECOMMENDED&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 ![Howard Johnson by Wyndham Staunton](//images.trvl-media.com/lodging/1000000/670000/663700/663617/99b5e75e_y.jpg) ### Howard Johnson by Wyndham Staunton 10/10 Excellent "I always stay here when visiting family in Staunton. The main reason? Because of the service!! They are so nice and accommodating! Yes, it is older and dated a bit, but they recently gave the place a fresh paint job and are doing their best. Thank you" [](https://expedia.ca/Staunton-Hotels-Howard-Johnson-By-Wyndham-Staunton.h663617.Hotel-Information) ![Motel 6 Staunton, VA](//images.trvl-media.com/lodging/1000000/10000/9000/8977/e2fd1c0e_y.jpg) ### Motel 6 Staunton, VA 10/10 Excellent "Staff was super / facility and well taken care of clean/ " [](https://expedia.ca/Staunton-Hotels-Motel-6-Staunton.h8977.Hotel-Information) ![Hotel 24 South](//images.trvl-media.com/lodging/2000000/1320000/1311400/1311324/76d25ca1_y.jpg) ### Hotel 24 South 10/10 Excellent "Beautiful downtown location. We loved the charm of the area." [](https://expedia.ca/Staunton-Hotels-Hotel-24-South.h1311324.Hotel-Information) ![Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes](//images.trvl-media.com/lodging/30000000/29860000/29852700/29852618/f4cdee3d_y.jpg) ### Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes 10/10 Excellent "Fantastic getaway close to the Mountain Inn and grocery, slopes are a short walk, as are beautiful trails and spectacular views. We brought our dog with us, and she also loved the place. We will definitely try to come back during the winter season. Five stars plus" [](https://expedia.ca/Charlottesville-Hotels-Wintergreen-Pet-Friendly-Condo-Wwifi.h29852618.Hotel-Information) ![Holiday Inn Express & Suites Staunton by IHG](//images.trvl-media.com/lodging/47000000/46550000/46550000/46549911/8e95e8a0_y.jpg) ### Holiday Inn Express & Suites Staunton by IHG 10/10 Excellent "Staff are amazing. Hotel is very functional and room is very spacious and practical. The only thing is that the room is not too sound proof. " [](https://expedia.ca/Staunton-Hotels-Holiday-Inn-Express-And-Suites-Staunton.h46549911.Hotel-Information) ![Holiday Inn Staunton Conference Center by IHG](//images.trvl-media.com/lodging/1000000/20000/19200/19125/c184cf6d_y.jpg) ### Holiday Inn Staunton Conference Center by IHG 10/10 Excellent "I have not had breakfast yet " [](https://expedia.ca/Staunton-Hotels-Holiday-Inn-Staunton-Conference-Center.h19125.Hotel-Information) ![Days Inn by Wyndham Waynesboro](//images.trvl-media.com/lodging/1000000/20000/13100/13044/b02f560b_y.jpg) ### Days Inn by Wyndham Waynesboro 10/10 Excellent "I really enjoyed my stay." [](https://expedia.ca/Staunton-Hotels-Days-Inn-By-Wyndham-Waynesboro.h13044.Hotel-Information) ![Holiday Inn Express & Suites Waynesboro East by IHG](//images.trvl-media.com/lodging/97000000/96550000/96546000/96545978/22c5f5c1_y.jpg) ### Holiday Inn Express & Suites Waynesboro East by IHG 10/10 Excellent "Clean room, well cared for property. Typical hotel breakfast " [](https://expedia.ca/Waynesboro-Hotels-Holiday-Inn-Express-And-Suites-Waynesboro-East.h96545978.Hotel-Information) ![Comfort Inn](//images.trvl-media.com/lodging/1000000/70000/64100/64084/2a69aac3_y.jpg) ### Comfort Inn 10/10 Excellent "Breakfast is good." [](https://expedia.ca/Staunton-Hotels-Comfort-Inn.h64084.Hotel-Information) ## Find out more about Wintergreen ## Wintergreen Vacation Homes information | Number of reviews | 303 | | --- | --- | | Accommodation | 414 Vacation Homes | | Lowest Price | CA $160 | | Highest Price | CA $1,093 | ## 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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