Bed and Breakfast Middlebrook

Ski-In/Ski-Out Wintergreen Resort Condo + Hot Tub!

Wintergreen Home w/ Hot Tub, Deck & Mountain Views

Pets-OK Retreat w Sauna, Jacuzzi at Wintergreen

Wintergreen Resort Home w/ 2 Decks + Ski Access!

New Field Farm at Timber Ridge

Wintergreen Ridge Retreat - Family Home

Serene Hideaway with Views, 1 Mi to Hike & Ski!

Waynesboro home near Wintergreen Charlottesville

Remote Equipped Bell Tent Surrounded by Nature with Great Hiking Trails in Virginia

Stoney Creek Cottage: Waterfront Hot Tub, Fire Pit

Cheval Circle Views, Hot Tub & Fire Pits

Altitude Adjustment

Spacious Home: 10 Miles to Wintergreen Resort!

Papas Cottage Hot Tub Near Nelson 151

Memes Cottage Near Nelson 151

Wine Country Modern Farmhouse on 10 Acres and Pool

Charming Cottage < 10 Mi to Wineries & Skiing!

Contemporary Mountain Holiday Home with Hot Tub

Time to Wine Down - Family Home

Afton Clubhouse

Afton Farmhouse

Monticello Wine Trail Cottage - Close to Hiking!

Mtn & Lake Views: Serene Wintergreen Resort Escape

The Cottage and Loft at Blue Rivers