Title: Book the Best ROMANTIC Hotels in Wintergreen, VA from CA $135 - Wintergreen Romantic Getaways | Expedia.ca [Hotels in Wintergreen](https://expedia.ca/Wintergreen-Hotels.d10811.Travel-Guide-Hotels)[Vacation Rentals in Wintergreen](https://expedia.ca/Wintergreen-Vacation-Rentals.d10811.Travel-Guide-VacationRentals)[Things to do in Wintergreen](https://expedia.ca/Things-To-Do-In-Wintergreen.d10811.Travel-Guide-Activities)[Wintergreen Car Rentals](https://expedia.ca/Car-Rentals-In-Wintergreen.d10811.Car-Rental-Guide)[Wintergreen Vacation Packages](https://expedia.ca/Wintergreen.d10811.Destination-Travel-Guides) ![Everything is frozen over at Wintergreen Resort. ](https://images.trvl-media.com/place/553248635996625639/07d79deb-5cfc-4068-8e41-c17e7657b695.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Melissa Smestad # Find Romantic Hotels in Wintergreen, VA from CA $135 - ![](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 availability on Wintergreen Romantic Hotels Tonight [Dec 9 - Dec 10](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-12-09&endDate=2025-12-10&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Dec 10 - Dec 11](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-12-10&endDate=2025-12-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Our top choices for Wintergreen romantic hotels ![Interior](https://images.trvl-media.com/lodging/69000000/68080000/68076800/68076715/3c2ad4b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68080000/68076800/68076715/79d4e134.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/69000000/68080000/68076800/68076715/b384df8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/69000000/68080000/68076800/68076715/48c0e694.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wintergreen. Sunset Vista Villa - Close to the ski slopes Wintergreen Resort 10/10 Exceptional (91) "Beautiful property! Had everything we needed and was very clean! Highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda W. CA $162 CA $363 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Charlottesville-Hotels-Stunning-Condo-Sunset-Vista-Villa.h68076715.Hotel-Information) ![](https://images.trvl-media.com/lodging/28000000/27770000/27767700/27767679/3ac798a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/28000000/27770000/27767700/27767679/12a54ff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27770000/27767700/27767679/b70b419a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/28000000/27770000/27767700/27767679/4641225d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2br/2ba: Million Dollar View from Luxury Condo on the Ridge. Roseland 9.0/10 Wonderful (302) "Great view!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Suzanne W. CA $123 CA $310 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Nellysford-Hotels-2br2ba-Million-Dollar-View-From-Luxury-Condo-On-The-Ridge.h27767679.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/60000000/59640000/59630800/59630794/f1eae07b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/60000000/59640000/59630800/59630794/735441eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/60000000/59640000/59630800/59630794/ba88ea81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/60000000/59640000/59630800/59630794/92ed7221.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views! Wintergreen Resort 9.8/10 Exceptional (137) "Perfect location right across from the village. Very comfortable and clean. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erin F. CA $346 CA $611 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Charlottesville-Hotels-Ski-Inski-Out-Condo-On-The-Slopes-Prime-Location-On-Eagles-Swoop.h59630794.Hotel-Information) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/73000000/72100000/72098800/72098776/42ee1156.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/73000000/72100000/72098800/72098776/373cf9be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72100000/72098800/72098776/7f9a963f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/73000000/72100000/72098800/72098776/6bd03936.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Black Bear Lodge: Stunning 4 Season Mountain Views! Perfect for Families. Pedlars Edge 9.8/10 Exceptional (33) "Well stocked fun house! Kind owners, views for days, comfy beds. We enjoyed a fun-filled weekend in the summer, cooked, played games. It was a dream vacay. Please note that there are limitations on resort amenities, but we went to Lake Sherando and had a great time." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) newsha d. [](https://www.expedia.ca/Nellysford-Hotels-Black-Bear-Lodge-Wintergreen-Sleeps-12-5bd4ba-Ski-Sky-More-Space-To-Play.h72098776.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1320000/1311400/1311324/76d25ca1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1320000/1311400/1311324/295808bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/2000000/1320000/1311400/1311324/75196b6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1320000/1311400/1311324/d544b47b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel 24 South Staunton 9.4/10 Exceptional (1039) "Super hotel in a super location! Very pleasant stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Timothy CA $147 CA $165 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Staunton-Hotels-Hotel-24-South.h1311324.Hotel-Information) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/19200/19125/c184cf6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/19200/19125/2c07af6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Accessible, Balcony (Communications)](https://images.trvl-media.com/lodging/1000000/20000/19200/19125/af7b76d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/19200/19125/ca172168.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Staunton Conference Center by IHG Staunton 8.2/10 Very good (1006) "safe parking area" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Walter CA $122 CA $135 total includes taxes & fees Jan 9 - Jan 10, 2026 [](https://www.expedia.ca/Staunton-Hotels-Holiday-Inn-Staunton-Conference-Center.h19125.Hotel-Information) ![Family Cottage](https://images.trvl-media.com/lodging/117000000/116900000/116890300/116890286/afbf6bb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic Cabin, Mountain View](https://images.trvl-media.com/lodging/117000000/116900000/116890300/116890286/c2ad2801.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116900000/116890300/116890286/ef9f98fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/117000000/116900000/116890300/116890286/741fee8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Iris Inn and Cabins Waynesboro 9.6/10 Exceptional (7) "Incredible Mountain View at Sunset. Extremely comfortable bed. Delicious breakfast." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dale CA $416 CA $463 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Waynesboro-Hotels-Iris-Inn-And-Cabins.h116890286.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/97000000/96790000/96788200/96788188/88d796ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96790000/96788200/96788188/7f9b3623.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sutherland | Mountain view](https://images.trvl-media.com/lodging/97000000/96790000/96788200/96788188/f3b309c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Travelers](https://images.trvl-media.com/lodging/97000000/96790000/96788200/96788188/b2a6a3de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Crossroads Inn North Garden 10/10 Exceptional (42) "The staff were excellent. Very friendly, great hospitality. We will definitely book again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sharon [](https://www.expedia.ca/North-Garden-Hotels-The-Crossroads-Inn.h96788188.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/39000000/38200000/38190400/38190375/4557b032.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cornwall](https://images.trvl-media.com/lodging/39000000/38200000/38190400/38190375/df3a4736.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![22-inch flat-screen TV with satellite channels, TV, iPod dock](https://images.trvl-media.com/lodging/39000000/38200000/38190400/38190375/05b11570.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Derby | Living area](https://images.trvl-media.com/lodging/39000000/38200000/38190400/38190375/b602ba8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Farmhouse at Veritas Afton 9.8/10 Exceptional (33) "Nice location a staff. Dining in the vineyard was excellent." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $304 CA $341 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Staunton-Hotels-The-Farmhouse-At-Veritas.h38190375.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/61000000/60840000/60831500/60831442/0f19da3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/61000000/60840000/60831500/60831442/2012780d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/61000000/60840000/60831500/60831442/ba906438.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/61000000/60840000/60831500/60831442/4bd96ca0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy cabin for 2 w/ great mt views & walking trails! Schuyler 10/10 Exceptional (172) "Gorgeous spot, and the cabin is very cozy and clean and has all the essentials, including smart TV and WiFi! Close to hiking trails, and not a far drive from wineries, breweries and a few restaurants. Sunsets are beautiful out back, and the location is quiet and peaceful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lauren CA $173 CA $241 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Schuyler-Hotels-Cozy-Cabin-For-2-W-Great-Mt-Views-Walking-Trails.h60831442.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-23&endDate=2025-12-24®ionId=10811&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top Wintergreen Hotel Reviews ![Amazing Mountain views - Ski In Ski Out - Wifi - fireplace - Pets OK ](https://images.trvl-media.com/lodging/19000000/19000000/18992300/18992227/3c332c07_y.jpg) ### Amazing Mountain views - Ski In Ski Out - Wifi - fireplace - Pets OK 10/10 Excellent "Amazing location. Wonderful sunrise view from porch. Walk to restaurants. We had a great time in Wintergreen." [](https://expedia.ca/Nellysford-Hotels-Amazing-Mountain-Views-Ski-In-Ski-Out-Wifi-Fireplace-Pets-OK.h18992227.Hotel-Information) ## Frequently asked questions ### Searching for romantic hotels in Wintergreen? ### When is the best time of year for a romantic getaway to Wintergreen? ### What is there to do in Wintergreen? ### What's the best way to get to Wintergreen and around town during my romantic getaway? ## 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) - [Apartments in Afton ](https://www.expedia.ca/Afton-Apartments.d6056907-aaApartments.Travel-Guide-Accommodation) - [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) - 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