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Welcome to Stay

What Stay offers is Unique

Welcome to Stay Wintergreen

We are proud to offer our guests the ability to stay in premier properties that are close to all of the activities and services of Wintergreen Resort, but have the comfort and convenience of a local home. We include all of the customer service and amenities of a hotel, while giving you the privacy you deserve during your stay. 

Feel free to book a property online or call us at (434) 509-0050 if you have questions or if we can help you with your plans while in town, including any of the activities below.



Wintergreen Activities

Wintergreen offers amazing outdoor activities, spa services, and fun events. From skiing to tennis to live music, there is something here for everyone.


Airport Transportation

Whether you are arriving or departing at CHO, RIC, or IAD, you will get the best private airport transportation pricing around through your Stay Wintergreen representative. 


Vineyard Trail Rides

Rebel's Run offers scenic horseback trail rides through beautiful Afton Mountain Vineyards with a short break for tastings, as well as riding lessons for adults and children.


Wine Tours

Offering free pickup from Wintergreen, Monticello Wine Tours offers private wine tours along the Monticello Wine Trail.