Private Mountain Getaway | Wintergreen Resort | House in Wintergreen Resort

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!

Private Mountain Getaway | Wintergreen Resort is located in Chestnut Springs. Private Mountain Getaway | Wintergreen Resort provides accommodation, featuring Pool, Balcony/Terrace, Guest Services, among other amenities. This House features Pool, Balcony/Terrace, Guest Services, to make your stay a comfortable one.

Private Mountain Getaway | Wintergreen Resort has 4 Bedrooms , 4 Bathrooms, and max occupancy of 13 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Chestnut Springs has interesting places to visit. If you want to learn more about the House in Chestnut Springs, such as places to visit and things to do nearby, you can check below to learn more.