Summary:

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.



The Space:

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!



Guest Access:

Guest has access to whole property



The Neighborhood:

Wintergreen Resort:



Perched on 11,000 breathtaking acres along the eastern slopes of the Blue Ridge Mountains, Wintergreen Resort is a true four‑season playground. Surrounded by winding trails, cascading streams, and lush forests, it’s the perfect place to unwind, explore, and reconnect with nature. Here you’ll find endless possibilities—whether you’re chasing outdoor adventure, indulging in relaxation, or gathering with family and friends.



In winter, carve through fresh powder with skiing (steps away from the house), snowboarding, and snow tubing. When the weather warms, tee off on 27 holes of championship golf at the Stoney Creek Course, play on award‑winning tennis courts, hike scenic mountain trails, cast a line fly fishing, or cool off with a refreshing swim. Pamper yourself at the full‑service mountaintop spa, then enjoy a variety of delicious dining options.



Whether you come for the crisp mountain air, the sweeping views, or the countless activities, Wintergreen Resort offers a refreshing escape and unforgettable memories in every season.



Getting Around:

Need transportation or trip planning?

We work with a private concierge service that will make your getaway effortless. Offering private transportation, wine and brewery tours, in‑home chefs, spa services, yoga, grocery delivery, and more. They’ll create a personalized experience so you can simply relax and enjoy. Ask host for more info.



Other Things to Note:

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.



Interaction with Guests:

Sunny Bear has a wonderful team. We want all our guest to have a 5 star experience. Customer service is important to us. Holly will be your main point of contact for bookings, questions, planning, check-in, and through your stay!