Title: 5 Stars Hotels in Wintergreen, Nellysford from CA $296 - Find Cheap Wintergreen Hotels With 5 Stars | Expedia.ca [Wintergreen Travel Guide](https://expedia.ca/Wintergreen.dx10811)[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)[Flights to Wintergreen](https://expedia.ca/Cheap-Flights-To-Wintergreen.d10811.Travel-Guide-Flights)[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 # 5 Stars Hotels in Wintergreen, Nellysford from CA $296 - ![](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 5 Star Hotels Tonight [Nov 2 - Nov 3](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-11-02&endDate=2025-11-03&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 3 - Nov 4](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-11-03&endDate=2025-11-04&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2025-11-07&endDate=2025-11-09&adults=2&star=50&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&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Wintergreen 5 Star Hotels ![Property entrance](https://images.trvl-media.com/lodging/97000000/96790000/96788200/96788188/88d796ff.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) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96790000/96788200/96788188/7f9b3623.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 (36) "Great staff, accommodations, and breakfast!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Windy [](https://www.expedia.ca/North-Garden-Hotels-The-Crossroads-Inn.h96788188.Hotel-Information) ![](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%2F5Star-Wintergreen-Hotels.s50-0-d10811.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Wintergreen-Hotels.s50-0-d10811.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Wintergreen. ![The Historic Berkeley Place](https://images.trvl-media.com/lodging/13000000/12640000/12636800/12636789/44cb9e02_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Historic Berkeley Place 303 Berkeley Place, Staunton, VA CA $195 CA $296 total Dec 1 - Dec 2 includes taxes & fees 9.2/10 Wonderful! (71 reviews) [](https://expedia.ca/Staunton-Hotels-Berkeley-House-Bed-And-Breakfast.h12636789.Hotel-Information) ![Iris Inn and Cabins](https://images.trvl-media.com/lodging/117000000/116900000/116890300/116890286/afbf6bb8_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Iris Inn and Cabins 191 Chinquapin Dr, Waynesboro, VA CA $422 CA $470 total Nov 3 - Nov 4 includes taxes & fees 9/10 Wonderful! (4 reviews) [](https://expedia.ca/Waynesboro-Hotels-Iris-Inn-And-Cabins.h116890286.Hotel-Information) ![Steeles Tavern Manor](https://images.trvl-media.com/lodging/11000000/10930000/10922900/10922847/519485f9_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Steeles Tavern Manor 8400 N Lee Hwy, Steeles Tavern, Raphine, VA CA $375 CA $433 total Nov 3 - Nov 4 includes taxes & fees 10/10 Exceptional! (27 reviews) [](https://expedia.ca/Lexington-Hotels-Steeles-Tavern-Manor.h10922847.Hotel-Information) Still don't see what you're looking for? [See all properties in Wintergreen.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F11%2F2025&endDate=04%2F11%2F2025®ionId=10811&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F11%2F2025&endDate=04%2F11%2F2025®ionId=10811&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F11%2F2025&endDate=04%2F11%2F2025®ionId=10811&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F11%2F2025&endDate=04%2F11%2F2025®ionId=10811&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F11%2F2025&endDate=04%2F11%2F2025®ionId=10811&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F11%2F2025&endDate=04%2F11%2F2025®ionId=10811&star=50&star=50&amenities=WATER_PARK) 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. ## Learn more about Wintergreen Nestled in the Blue Ridge Mountains, this four-season resort offers skiing in winter and championship golf courses in summer. Hike to stunning Crabtree Falls nearby or explore the scenic Blue Ridge Parkway with its overlooks and picnic spots. [See all hotels in Wintergreen](https://www.expedia.ca/Hotel-Search?startDate=2025-11-16&endDate=2025-11-17&adults=2®ionId=10811) ![Overlook near Wintergreen Ski Resort](https://images.trvl-media.com/place/10811/f7c97680-28b4-457d-9bcc-051a2160b6d3.jpg?impolicy=fcrop&w=899&h=675&p=1&q=high) Photo by Rebecca Brent ## Top Wintergreen Hotel Reviews ## Find out more about Wintergreen ## Five Star Hotels in Wintergreen There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Wintergreen so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Wintergreen and get ready to be pampered like never before. #### Get a Great Deal on 5-Star Hotels in Wintergreen Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places. Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town. #### Make Your Escape to Wintergreen The results are in, and Wintergreen 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Wintergreen! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Wintergreen today and settle down in the lap of luxury tomorrow. ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Wintergreen? > How much you pay for a 5-star hotel in Wintergreen depends on factors like when you want to go and the length of your escape. A top tip for scoring an awesome deal? Use our pricing filters to compare the available options for your selected dates. > > > > - Search for the lowest price per night from CA $296 ### What makes a hotel 5 stars in Wintergreen? > From fine dining venues and fitness centres to swimming pools and luxury bedding, the 5-star experience in Wintergreen is all about indulgence and comfort. But it takes more than just top-notch amenities to get a 5-star rating. Stays also have to offer superior services like beauty treatments, on-site laundry and dry cleaning and concierge services. ### Are there any 5-star all-inclusive resorts in Wintergreen? > Find a luxury stay that includes your lodging, meals, bar and entertainment in Wintergreen with our filter tool. Search for resorts rated 5 stars and click on the "All inclusive" filter. Have a look at what's included in the purchase price. 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