Title: Wintergreen Guest Houses from CA $291 | 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 # Search Guest Houses in Wintergreen from CA $291 ![](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 [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-12-12&endDate=2025-12-14&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Wintergreen Guest Houses ![Property grounds](https://images.trvl-media.com/lodging/27000000/26680000/26679500/26679424/a8c9acaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, Private Bathroom (Entire Property) | Outdoor pool](https://images.trvl-media.com/lodging/27000000/26680000/26679500/26679424/95fcd077.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa, Private Bathroom (Suite 6) | Lounge](https://images.trvl-media.com/lodging/27000000/26680000/26679500/26679424/a796341c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room](https://images.trvl-media.com/lodging/27000000/26680000/26679500/26679424/217d95d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Afton Mountain Inn Afton 9.6/10 Exceptional (70) "Clean room and very nice amenities with multiple outside sitting areas. Traffic noise was excessive particularly in the front bedrooms. No staff on premises, but replies to questions were returned very quickly." ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Owen CA $195 CA $298 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Afton-Hotels-Afton-Mountain-Inn.h26679424.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/13000000/12640000/12636800/12636789/44cb9e02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Ensuite (The Shenandoah) | Miscellaneous](https://images.trvl-media.com/lodging/13000000/12640000/12636800/12636789/a4b4b894.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/13000000/12640000/12636800/12636789/97003e23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12640000/12636800/12636789/7aaf4a85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Historic Berkeley Place Staunton 9.2/10 Wonderful (135) "Everything is really nice the drinks and snacks that they had that you could get were really nice the rooms are really nice also" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Beverly CA $234 CA $341 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Staunton-Hotels-Berkeley-House-Bed-And-Breakfast.h12636789.Hotel-Information) ![Signature Suite, Private Bathroom (Suite 5)](https://images.trvl-media.com/lodging/111000000/110380000/110377800/110377780/ecf94814.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, Private Bathroom (Suite 4) | Lounge](https://images.trvl-media.com/lodging/111000000/110380000/110377800/110377780/d604ea23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Suite, Private Bathroom (Suite 2) | Exterior](https://images.trvl-media.com/lodging/111000000/110380000/110377800/110377780/b1104fa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/111000000/110380000/110377800/110377780/5c6b512f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Barristers Row Staunton 7.6/10 Good (5) "The room was very nice" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) william CA $175 CA $291 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Staunton-Hotels-Barristers-Row.h110377780.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/105000000/104870000/104864200/104864197/12738a4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/105000000/104870000/104864200/104864197/8e5abb89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/105000000/104870000/104864200/104864197/9c5a2fda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/105000000/104870000/104864200/104864197/b58915c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Historic Inn at Oakdene Staunton 9.4/10 Exceptional (12) "We stayed here for our anniversary and we loved it. The house itself is beautiful inside and out. Great spaces to convene for a tasty drink and a room to play a little pool. This Inn is in walking distance to downtown. Quite a lovely stroll, passing by history galore. " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Christie CA $245 CA $369 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Staunton-Hotels-The-Historic-Inn-At-Oakdene.h104864197.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=2025-11-01&endDate=2025-11-02®ionId=10811&adults=2&lodging=GUEST_HOUSE&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-Guest-Houses.d10811-aaGuestHouses.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWintergreen-Guest-Houses.d10811-aaGuestHouses.Travel-Guide-Accommodation) ## Top Wintergreen Hotel Reviews ![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 "Was the perfect place for us! Loved that there was a fireplace, made it super cozy! " [](https://expedia.ca/Charlottesville-Hotels-Wintergreen-Pet-Friendly-Condo-Wwifi.h29852618.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 "Very nice! Great place. " [](https://expedia.ca/Nellysford-Hotels-NEW-Modern-Mountain-Condo-WPool.h77096798.Hotel-Information) ![Sleep Inn Staunton](//images.trvl-media.com/lodging/1000000/170000/168400/168389/f334eca9_y.jpg) ### Sleep Inn Staunton 10/10 Excellent "Breakfast was very minimal. Clean room. " [](https://expedia.ca/Staunton-Hotels-Sleep-Inn-Staunton.h168389.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 "Very nice room. Breakfast was good as well" [](https://expedia.ca/Staunton-Hotels-Best-Western-Staunton-Inn.h18431.Hotel-Information) ![Hotel 24 South](//images.trvl-media.com/lodging/2000000/1320000/1311400/1311324/76d25ca1_y.jpg) ### Hotel 24 South 10/10 Excellent "Awesome" [](https://expedia.ca/Staunton-Hotels-Hotel-24-South.h1311324.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 "Clean Property, excellent check-in super staff, especially in the hotel restaurant lounge area. Staff seems to be a little over work, but works completely as a team which makes that issue not issue for the customer you can tell they’re tired. Rooms are very clean. Parking is great close to the interstate. The only thing I would have to say is the hotel is a little worn out. Needs to update. We would stay there again " [](https://expedia.ca/Staunton-Hotels-Holiday-Inn-Staunton-Conference-Center.h19125.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 "Great, parked outside of the room…very well lit parking area. Staff was friendly. Room clean. " [](https://expedia.ca/Staunton-Hotels-Motel-6-Staunton.h8977.Hotel-Information) ![NEW! Warren’s Woods! Spacious 5-bedroom house in fantastic Wintergreen Resort](//images.trvl-media.com/lodging/119000000/118930000/118927400/118927334/3fa11b26_y.jpg) ### NEW! Warren’s Woods! Spacious 5-bedroom house in fantastic Wintergreen Resort 10/10 Excellent "We had a fabulous stay at Warren’s Woods! The location of the house is perfectly situated within Wintergreen, a short walk or drive to hiking and the main resort facilities. We enjoyed the hot tub and wood burning fireplace. The kitchen was very well stocked and the layout of the house was great for 2 families. We’ll be back! 5 stars! " [](https://expedia.ca/Nellysford-Hotels-NEW-Warrens-Woods-Spacious-5-Bedroom-House-In-Fantastic-Wintergreen-Resort.h118927334.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 "Clean and friendly. " [](https://expedia.ca/Staunton-Hotels-Holiday-Inn-Express-And-Suites-Staunton.h46549911.Hotel-Information) ## Find out more about Wintergreen ## Wintergreen Guest Houses information | Number of reviews | 155 | | --- | --- | | Accommodation | 5 Guest Houses | | Lowest Price | CA $291 | | Highest Price | CA $369 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [2 Star Hotels in Deer Springs](https://www.expedia.ca/2Star-Deer-Springs-Nellysford-Hotels.s20-n553248635976470298-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Afton](https://www.expedia.ca/Afton-Hotels-Cheap-Hotels.0-0-d6056907-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Bar in Afton](https://www.expedia.ca/Afton-Hotels-Hotels-With-Bar.0-0-d6056907-tHotelswithBar.Travel-Guide-Filter-Hotels) - [Mountain Hotels in Afton](https://www.expedia.ca/Afton-Hotels-Mountain-Hotels.0-0-d6056907-tMountainHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Afton](https://www.expedia.ca/Afton-Hotels-Pet-Friendly-Hotel.0-0-d6056907-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - 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[Flights from Faber](https://www.expedia.ca/lp/flights/6353692/flights-from-faber) - [Visit Blue Ridge Tunnel Trail](https://www.expedia.ca/Blue-Ridge-Tunnel-Trail.dx847217400490500096) - [Lovingston Winery](https://www.expedia.ca/Lovingston-Winery-Lovingston.d553248621532658155.Vacation-Attraction) - [Rockfish Gap Entrance Shenandoah](https://www.expedia.ca/Rockfish-Gap-Entrance-Shenandoah-Waynesboro.d6129965.Vacation-Attraction) - [Visit Roseland](https://www.expedia.ca/Roseland.dx6361484) - [Visit Tyro](https://www.expedia.ca/Tyro.dx3000460704) - [Visit Waynesboro](https://www.expedia.ca/Waynesboro.dx6733) - [Car rental Afton](https://www.expedia.ca/Car-Rentals-In-Afton.d6056907.Car-Rental-Guide) - [Car rental Tyro](https://www.expedia.ca/Car-Rentals-In-Tyro.d3000460704.Car-Rental-Guide) - [Car rentals near Veritas Vineyard and Winery](https://www.expedia.ca/Car-Rentals-In-Veritas-Vineyard-And-Winery.d6093181.Car-Rental-Guide) - [Car rentals near Wintergreen Resort](https://www.expedia.ca/Car-Rentals-In-Wintergreen-Resort.d6093285.Car-Rental-Guide) - 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