Title: Wintergreen Vacation Home Rentals from CA $685: 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 ### Change your mind Book hotels with free cancellation ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-10-17&endDate=2025-10-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Wintergreen Vacation Homes ![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/121000000/120110000/120102000/120101948/23743ed1.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) ### Wintergreen Ridge Retreat - Family Home Pedlars Edge CA $450 CA $843 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Nellysford-Hotels-Wintergreen-Ridge-Retreat-Family-Home.h120101948.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/117000000/116770000/116764000/116763931/w1162h853x2y0-b806e302.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116770000/116764000/116763931/fd8fe148.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/117000000/116770000/116764000/116763931/02b581a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/117000000/116770000/116764000/116763931/7adff27b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 2-bedroom condo in beautiful Wintergreen Resort Wintergreen Resort 10/10 Exceptional (1) "We stayed here for a couple of nights over July 4th and it was a nice short getaway. The condo is in a good location - 5 min walk to resort restaurants - and is very comfortable. The kitchen is well-equipped with plenty of cooking tools. The living room seating space was comfortable and allowed for just hanging out. We really enjoyed our stay! " CA $209 CA $523 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Nellysford-Hotels-Charming-2-Bedroom-Condo-In-Beautiful-Wintergreen-Resort.h116763931.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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/112000000/112000000/111999900/111999850/01848675.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!" CA $642 CA $1,390 total includes taxes & fees Nov 5 - Nov 6 [](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/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 (6) "The house was beautiful and well stocked. The owner thought of everything and all the light switches were labeled which helped a lot. All of the appliances were top notch and the Keurig coffee maker had everything that was needed. Beds were very comfortable and each room had its own thermostat. Overall, excellent stay!" CA $285 CA $622 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Nellysford-Hotels-The-Distinguished-Squirrel-Chalet-Walking-Distance.h112532111.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. Dog-friendly! Close to hiking. Wintergreen Resort 10/10 Exceptional (23) "The bed was very comfortable and the hot tub was perfect. Enjoyed the views" CA $213 CA $526 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Nellysford-Hotels-New-Listing-3-Min-To-Ski-Whot-Tub-And-Fireplace-Dog-Friendly.h90127668.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71970000/71970000/71969999/74b5408b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/72000000/71970000/71970000/71969999/3fa3435d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/72000000/71970000/71970000/71969999/6a324828.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71970000/71970000/71969999/ae868c04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite! Treeloft 10/10 Exceptional (62) "Loved our stay - the house, location, and amenities were perfect for us!" CA $558 CA $995 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Nellysford-Hotels-Modern-Luxe-Treetop-Retreat-WGas-Fire-Pit.h71969999.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) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/108000000/107020000/107020000/107019915/4d8bd641.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) ### Tucked Inn: Lower Unit - NEW Nelson Co Getaway Nellysford CA $139 CA $399 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Nellysford-Hotels-Tucked-Inn-Lower-Unit-NEW-Nelson-Co-Getaway.h107019915.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 (7) "Home was as described. Location was close enough to stores and attractions. Hot tub was nice." CA $179 CA $488 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Waynesboro-Hotels-The-Hawksbill-Haus.h87135309.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) ![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) ![Interior](https://images.trvl-media.com/lodging/89000000/88370000/88365700/88365665/w1017h683x4y0-17be165b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Firefly Springhouse Staunton 9.8/10 Exceptional (38) "What a great place to stay! It is such a cute space, and the owners were wonderful! If you love a farm there are plenty of chickens, goats and even a couple of peacocks! We will definitely be back! It was a perfect for our last minute quick getaway! " CA $115 CA $160 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Staunton-Hotels-The-Firefly-Springhouse.h88365665.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/104000000/103170000/103166000/103165960/59b2fe3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103170000/103166000/103165960/4011514a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103170000/103166000/103165960/1a04761a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/104000000/103170000/103166000/103165960/4cf77170.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tucked Inn: Upper Unit - 151 Getaway/Wine + Brews Nellysford 10/10 Exceptional (4) "We had a brief stay but it had all the amenities we needed and was very clean and welcoming. Thank you." CA $155 CA $426 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Nellysford-Hotels-NEWTucked-Inn-Upper-Unit-151-Getaway.h103165960.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) ![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) ![TV, books](https://images.trvl-media.com/lodging/89000000/88370000/88369700/88369669/1a8b755b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/89000000/88370000/88369700/88369669/6614261a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Bungalow 30 minutes from Wintergreen Roseland 10/10 Exceptional (13) "I love this place. I’ve stayed there one previous time and it was just as wonderful. Peaceful beautiful home for a relaxing vacation." CA $133 CA $339 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Roseland-Hotels-Historic-Bungalow-30-Minutes-From-Wintergreen.h88369669.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106210000/106201300/106201278/daf9d100.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106210000/106201300/106201278/e50348ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/107000000/106210000/106201300/106201278/32baa0ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/107000000/106210000/106201300/106201278/fe2eb49d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Secluded 20+ Acre Retreat Near Brew & Wine Trails Afton 9.8/10 Exceptional (8) "Everything was exactly as stated. We loved the house and the close proximity to the 151. We will definitely come back! " [](https://www.expedia.ca/Afton-Hotels-Secluded-20-Acre-Retreat-Near-Brew-Wine-Trails.h106201278.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/71000000/70430000/70420900/70420899/074dfa7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/71000000/70430000/70420900/70420899/bd5326d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/71000000/70430000/70420900/70420899/cc1789fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/71000000/70430000/70420900/70420899/65bdb166.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Afton Farmhouse - Mountain Views off Route 151 Afton 9.8/10 Exceptional (25) "Beautiful location and property!" CA $264 CA $667 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Afton-Hotels-Afton-Farmhouse-Mountain-Views-Off-Route-151.h70420899.Hotel-Information) ![House](https://images.trvl-media.com/lodging/121000000/120110000/120102000/120101946/4589d2ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/121000000/120110000/120102000/120101946/e69e5e1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/121000000/120110000/120102000/120101946/94cccf49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/121000000/120110000/120102000/120101946/a8e2dfaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Love Afton Cabin - Family Home Afton CA $1,048 CA $1,769 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Afton-Hotels-Love-Afton-Cabin-Family-Home.h120101946.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105300000/105296900/105296860/56c5cc48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/106000000/105300000/105296900/105296860/601ed46a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105300000/105296900/105296860/6a33b71d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105300000/105296900/105296860/db3adc00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious Estate on 6 acres, King Suite + Efficiency convenient to I-64 in Crozet Charlottesville 9.0/10 Wonderful (2) "Check in was super convenient and seamless and the house was in a fantastic location with a beautiful sunrise over the road. Hosts were fantastic and hugely supportive when unexpected maintenance issues came up. Very communicative and helpful!" CA $474 CA $765 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Charlottesville-Hotels-Discover-Rural-Charm-Near-Local-Attractions-At-Meadowview-Acres.h105296860.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) ![Exterior detail](https://images.trvl-media.com/lodging/72000000/71120000/71112300/71112269/7c2e5c8e.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 (18) "Beautiful home, very comfortable, and uniquely fun decor. Highly recommend!" CA $132 CA $232 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Waynesboro-Hotels-The-Loriann.h71112269.Hotel-Information) ![House](https://images.trvl-media.com/lodging/121000000/120110000/120102000/120101921/bc41ade7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/121000000/120110000/120102000/120101921/1b3fc888.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/121000000/120110000/120102000/120101921/4c201712.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/121000000/120110000/120102000/120101921/ff95e47f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Time to Wine Down - Family Home Afton CA $630 CA $978 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Afton-Hotels-Time-To-Wine-Down-Family-Home.h120101921.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/91000000/90240000/90233100/90233010/w1500h999x0y1-1e997f3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/91000000/90240000/90233100/90233010/b88f740f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, internet, bed sheets](https://images.trvl-media.com/lodging/91000000/90240000/90233100/90233010/a21765c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90240000/90233100/90233010/bd578acb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ridgeview Retreat: Mountain Views and Pet Friendly Staunton 10/10 Exceptional (12) "Great property in a great location!" CA $266 CA $641 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Staunton-Hotels-Ridgeview-Retreat-Mountain-Views-And-Pet-Friendly.h90233010.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) ![TV](https://images.trvl-media.com/lodging/91000000/90240000/90233100/90233022/c2f4237e.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) ![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) ### The Hunker Down: Cheerful 2 Bed and Pet Friendly Staunton 9.0/10 Wonderful (13) "The property and location were great. The description stating that the upstairs is also a rental and can have noise is definitely true and needs to be considered. The upstairs was rented during our stay and it sounded like a herd of elephants stomping through the builiding between midnight and 2am on our only night there. Not sure I would do it again. " CA $181 CA $370 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Staunton-Hotels-The-Hunker-Down-Cheerful-2-Bed-And-Pet-Friendly.h90233022.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) ![Interior](https://images.trvl-media.com/lodging/104000000/103710000/103700200/103700145/120039e2.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) ### Little Yellow House: Walk to Downtown Staunton Staunton 10/10 Exceptional (5) "I loved the location and the extra amenities !" CA $138 CA $395 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Staunton-Hotels-Little-Yellow-House-Walk-To-Downtown-Staunton.h103700145.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=2025-10-21&endDate=2025-10-22®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 ![Howard Johnson by Wyndham Staunton](//images.trvl-media.com/lodging/1000000/670000/663700/663617/932add2a_y.jpg) ### Howard Johnson by Wyndham Staunton 10/10 Excellent "Meh" [](https://expedia.ca/Staunton-Hotels-Howard-Johnson-By-Wyndham-Staunton.h663617.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 "We stayed here twice in one week for the halfway point of our trip to Pigeon Forge. I would definitely recommend. The hotel was very clean, staff was very friendly and the breakfast was decent! " [](https://expedia.ca/Waynesboro-Hotels-Holiday-Inn-Express-And-Suites-Waynesboro-East.h96545978.Hotel-Information) ![The Modern Mountain Condo ](//images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/53d40131_y.jpg) ### The Modern Mountain Condo 10/10 Excellent "Great little condo for a quick getaway for a wedding. Spent very little time in the unit, but convenient, affordable and very clean!" [](https://expedia.ca/Nellysford-Hotels-NEW-Modern-Mountain-Condo-WPool.h77096798.Hotel-Information) ![Hotel 24 South](//images.trvl-media.com/lodging/2000000/1320000/1311400/1311324/76d25ca1_y.jpg) ### Hotel 24 South 10/10 Excellent "Beautiful, walkable area!" [](https://expedia.ca/Staunton-Hotels-Hotel-24-South.h1311324.Hotel-Information) ![avid hotel Staunton by IHG](//images.trvl-media.com/lodging/1000000/20000/17600/17558/3f6256d5_y.jpg) ### avid hotel Staunton by IHG 10/10 Excellent "Nice, clean, comfortable. Just remember, Avid doesn't have a coffee maker in the room. But, fresh coffee is always available in the lobby. " [](https://expedia.ca/Staunton-Hotels-Avid-Hotels-Staunton.h17558.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 very friendly. Pets were welcome without an additional fee." [](https://expedia.ca/Staunton-Hotels-Motel-6-Staunton.h8977.Hotel-Information) ![Sleep Inn Staunton](//images.trvl-media.com/lodging/1000000/170000/168400/168389/f334eca9_y.jpg) ### Sleep Inn Staunton 10/10 Excellent "We stayed 4 nights at the Sleep Inn in Staunton and have no complaints at all. The beds were comfortable, the staff was fabulous, and the breakfast was good each morning. I would definitely recommend this hotel and will stay here again if I'm ever back in the area." [](https://expedia.ca/Staunton-Hotels-Sleep-Inn-Staunton.h168389.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 "The property was in great condition. The staff was very courteous. The breakfast was pretty standard fare, but somehow... better than other, similar establishments." [](https://expedia.ca/Staunton-Hotels-Holiday-Inn-Express-And-Suites-Staunton.h46549911.Hotel-Information) ![Best Western Staunton Inn](//images.trvl-media.com/lodging/1000000/20000/18500/18431/5e29fbfa_y.jpg) ### Best Western Staunton Inn 10/10 Excellent "Overall condition was good , staff friendly and accommodating " [](https://expedia.ca/Staunton-Hotels-Best-Western-Staunton-Inn.h18431.Hotel-Information) ## Find out more about Wintergreen ## Wintergreen Vacation Homes information | Number of reviews | | | --- | --- | | Accommodation | 414 Vacation Homes | | Lowest Price | CA $685 | | Highest Price | CA $1,769 | ## 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) - 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