Vacation Rentals

1639 Overlook is a recently renovated four-bedroom, four-bath Wintergreen condo with panoramic mountain views, golf course proximity, and small-dog-friendly policy. 1639 Overlook was recently renovated to showcase four bedrooms, four baths, pet-friendly policies for small dogs, and sweeping Wintergreen vistas beside the golf course.

Cozy & Clean Wintergreen Condo features a new king bed, plush linens, fireplace, smart TVs, and dog-friendly patio one mile from the resort core. This is a well-behaved dog friendly and non-smoking condo.

Directly on the slope of Eagle's Swoop, our condo is in a central location to everything in Wintergreen Resort! Enjoy a true ski in/ski out experience with stunning mountain views. Park your car in our designated parking spot and walk to The Market at Wintergreen, the Skyline Pavilion (Ski Rental & Lift Ticket Office), and The Edge & Coppermine restaurants that overlook the slopes.

Pepper's Mountain Pad is a two-bedroom Wintergreen condo walking distance to The Market, village, and Laurelwood pool with wood-burning fireplace, smart TVs, stocked kitchen, and private patio. Peppers Mountain Pad feels like your own village pied-à-terre—walk to The Market or Laurelwood pool, then settle in by the wood-burning fireplace or stream a movie on the smart TVs.

Slipper Slope is a four-bedroom ski-in/ski-out condo on Upper Diamond Hill with spacious layout and true ground-level slope access. Hard to find a bottom floor ski in ski out, especially with 4 bedroom, very spacious.

Three Ridge Retreat is a two-bedroom, two-bath dog-friendly Wintergreen condo within walking distance of slopes, restaurants, and resort trails.

Wintergreen – Fairway Woods is a two-bedroom resort condo with cozy fireplace, balcony seating, and electric grill overlooking the Blue Ridge. The resort is found on the Sunrise Side of the Blue Ridge Mountains and is conveniently located close to Charlottesville, Staunton, Lynchburg, and Waynesboro.

Wintergreen 19 Ivy Glen Lane is a four-bedroom, 3.5-bath end-unit townhouse with two-car garage, steps from shuttle stop, spa, pools, golf, tennis, and hiking.<br><br>19 Ivy Glen Lane brings townhouse convenience to Wintergreen—four bedrooms, 3.5 baths, two-car garage, and front-door access to shuttles, spa amenities, pools, golf, and tennis.