Private Mountain Getaway Wintergreen Resort

Unplug and unwind at 'Sunny Bear 'at Wintergreen Resort, VA. A peaceful mountain retreat tucked away yet close to resort amenities. Perfect for families, couples, or friends, this home features a stunning floor-to-ceiling stone fireplace, spacious decks for morning coffee or stargazing, and plenty of space to relax and reconnect. With seasonal pool access, skiing, winter activities, tennis, pickleball, and Appalachian Trail hiking nearby, it’s the perfect blend of comfort, nature, and adventure.

Sunny Bear is a welcoming mountain home where families and friends can relax, reconnect, and enjoy time together at Wintergreen Resort. Set in a peaceful area of the resort, the home feels tucked away while still offering easy access to year-round activities.

Inside, the open living space invites everyone to gather around the floor-to-ceiling stone wood burning fireplace after a day of skiing, hiking, or exploring the mountains (firewood provided). The kitchen and dining area are designed for shared meals, games, and easy conversation.

The home offers three bedrooms plus a bonus room, providing comfortable sleeping arrangements for larger groups. The primary bedroom features a queen bed with an adjoining en suite bathroom, the second bedroom includes a queen and a twin, and the third bedroom offers two queens and two twins. Ideal for kids or multiple families traveling together. The bonus room includes a pull-out couch with a thick memory foam mattress that guests consistently find extremely comfortable.

Large decks provide space to enjoy fresh mountain air, seasonal views, and quiet evenings under the stars. Sunny Bear is an ideal home base for creating lasting mountain memories.

Same-Day Bookings: Please contact the host prior to booking to confirm the home has been cleaned and is available.

***Minimum Booking Age: 24+
We kindly request that no parties take place, and guests must be 24 years of age or older to book the home. Thank you for your cooperation!

Wintergreen Ski Resort offers 26 runs across 129 skiable acres, vibrant après‑ski dining, night skiing on 45 acres, and Virginia’s largest snow tubing hill—The Plunge

Discovery Ridge Adventure Center features rock climbing, bungee trampolines, a 25‑ft climbing tower, gem mining, disc golf, 18‑hole mini golf, ninja course, archery, and mechanical bull rides.

✨ Wintergreen Activities (On‑Site & Nearby)

Wintergreen Resort Tennis and Pickleball Courts - 2 min

Chestnut Springs Pool (on‑mountain) – 3 min

Wintergreen Spa - 5 min

Wintergreen Ski Resort Base Lodge – 7 min

The Plunge Snow Tubing Park – 7 min

Discovery Ridge Adventure Center – 7 min

Shamokin Springs Nature Preserve – 8 min

Stoney Creek Golf Course – 21 min

🍷 Wine & Beer
Devil’s Backbone Brewpub – 15 min

Three Notch’d Brewing - 20 min

Hill Top Berry Farm & Winery – 20 min

Bold Rock Nellysford Cidery - 20 min

Wood Ridge Farm Brewery – 35 min

Seven Arrows Brewing Company – 35 min

Blue Mountain Brewery – 40 min

Veritas Vineyards & Winery – 40 min

Afton Mountain Vineyards – 40 min

🥾 Hiking Highlights
Highlands Leisure Trail – 4 min

Upper Shamokin Falls Trail – 5 min

Appalachian Trail Head – 15 min

Blue Ridge Parkway – 8 min

Three Ridges Overlook – 10 min

Appalachian Trail – Three Ridges Hike – 10 min

Crabtree Falls – 35 min

✈️ Airport
Charlottesville–Albemarle Airport – 1 hr

💧 Water & Pool Access
Chestnut Springs Pool (on‑mountain) – 3 min

Rodes Farm Pool (valley) – 25 min

Lake Monocan (Stoney Creek) – 25 min

Sherando Lake Recreation Area – 30 min

Water Activities & Pool Access
Guests may use the HOA pools at Chestnut Springs (on‑mountain) and Rodes Farm (valley) from Memorial Day weekend through Labor Day.

Lake Monocan (20-acre resort lake at 239 Camping Ridge Lane, Stoney Creek) offers swimming, aqua cycles, paddleboards, kayaks, snack bar, and grills; day-use fees please check on Wintergreen Resort Website.

Sherando Lake Recreation Area features a scenic 25-acre spring-fed lake with sandy beaches, shaded picnic areas, rustic architecture, and adjacent trailheads. Day-use is $8 per vehicle (up to eight passengers).

Important Resort Policy Update:
As of newly enacted Wintergreen Resort policy: unaccompanied guests (renters) cannot access the gym, indoor pool, or Devils Knob golf course.