Wineries ★ Host pick 151 Veritas Vineyards and Winery 26 min · 18.3 mi from the house 151 VERITAS LANE | AFTON, VA | 540.456.8000 Nestled at the base of the Blue Ridge Mountains outside Charlottesville, Veritas Vineyards and Winery is… Details →
Wineries ★ Host pick King Family Vineyards 34 min · 25.3 mi from the house 6550 ROSELAND FARM | CROZET, VA 22932 | 434.832.7800 King Family Vineyards is a family owned and operated winery located at the foothills of the Blue… Details →
Wineries ★ Host pick Septenary Winery at Seven Oaks Farm 29 min · 22.5 mi from the house 200 SEVEN OAKS FARM | GREENWOOD, VA 22943 | 434.996.6292 Situated on 109 acres of rolling hills surrounded by the Blue Ridge Mountains, Seven Oaks… Details →
Wineries ★ Host pick 151 Hazy Mountain Vineyards & Brewery 27 min · 19.6 mi from the house 240 HAZY MOUNTAIN LN | AFTON, VA 22920 | 540.302.2529 Hazy Mountain is our Estate Vineyard, currently with 35 acres under vine and growing. First… Details →
Breweries ★ Host pick 151 Devils Backbone Basecamp Brewpub 7 min · 4.7 mi from the house Devil’s Backbone Basecamp Brewpub 200 MOSBYS RUN | ROSELAND, VA 22967 | 434.361.1001 Experience the captivating Devil’s Backbone Brewing Company in… Details →
Breweries ★ Host pick 151 Three Notch'd Brewery, Distillery & Craft Kitchen - Nelson County 11 min · 7.2 mi from the house 2461 ROCKFISH VALLEY HWY | NELLYSFORD, VA 22958 Three Notch’d Brewing Company was conceived by three friends who value great beer and great times,… Details →
Cideries ★ Host pick 151 Bold Rock Nellysford Cidery 9 min · 5.9 mi from the house 1020 ROCKFISH VALLEY HWY | NELLYSFORD, VA 22958 | 434.361.1030 Winner of over 100 awards, Bold Rock’s cider can now be found throughout the… Details →
Cideries ★ Host pick 151 Blue Toad Hard Cider - Cidery & Event Barn 8 min · 4.6 mi from the house 462 WINERY LANE | ROSELAND, VA 22967 | 434.760.9200 Born in a barn, Blue Toad Cider honors the tradition and legacy of America’s first preferred… Details →
Activities Nelson Farmers Market Cooperative May through October – Saturdays 8:00 am -12 pm A wide variety of local produce, bakery items, live music and more. Details →
Activities Critzer Family Farm 34 min · 23 mi from the house Veggie and fruit picking. Homemade ice cream! Details →
Activities Polo at King Family Vineyards Roseland Polo matches are free and open to the public. No reservations are required. For a list of Food Trucks that will be on-site on specific… Details →
Activities Apple Picking at Dickie Brothers Orchard 24 min · 14.9 mi from the house 9519 CRITZERS SHOP ROAD | AFTON, VA 22920 | 540.456.8020 DICKIE BROS. ORCHARD is one of the oldest family owned and operated farms in the USA. Dickie… Details →
Activities South River Fly Shop With the Shenandoah, James, and Jackson Rivers, and numerous creeks all within easy reach, the area has a lot to offer a fly fisherman or someone… Details →
Activities Camp Wintergreen The Treehouse Facility is now home to Camp Wintergreen for campers ages 5 to 12 years old. We will focus on different weekly themes to enlighten,… Details →
Activities Discovery Ridge Adventure Center Adventure Center - Indoor fun including Ninja Warrior Course and bouldering wall - Outdoor activities including bungee trampoline, gem mining,… Details →
Activities The Plunge Snow Tubing Park Virginia's largest snow tubing park — a 900-foot hill with 10 lanes and speeds up to 40 mph, right at the resort base by the Blue Ridge Express… Details →
Activities Wintergreen Playgrounds Wintergreen has three free playgrounds, all open to the public during daylight hours. Chestnut Springs (beside the mountain pool) is smaller and… Details →
Activities Wintergreen Ski Area — Lift Tickets & Rentals Wintergreen's slopes are open to anyone who buys a lift ticket — 26 trails across beginner greens and the steeper Highlands and Dobie runs, plus… Details →
Activities Wintergreen Spa at Devils Knob A full-service resort spa open to everyone — no membership required. Massages, facials, body treatments, and nail care in a calm mountaintop setting… Details →
Wineries Caihailian Vineyard 6 min · 4 mi from the house 872 Beech Grove Rd | Roseland, VA 24472 | 571 Caihailian Vineyard, owned by Bob and Anne Ramsey, is a boutique winery located in the Monticello AVA,… Details →
Wineries Jefferson Vineyards 49 min · 41.2 mi from the house Thomas Jefferson and Philip Mazzei chose the very same site when they grew grapes here almost 250 years ago. Back then, our estate was the site of… Details →
Wineries Pippin Hill Farm & Vineyards 36 min · 29.9 mi from the house 5022 PLANK RD, NORTH GARDEN, VA | 434.202.8063 As the culmination of seed and earth and climate, of sun and dirt and vine, wine becomes the distilled… Details →
Wineries Mountain Cove Vineyards 33 min · 25 mi from the house 240 HAZY MOUNTAIN LN | AFTON, VA 22920 | 540.302.2529 Hazy Mountain is our Estate Vineyard, currently with 35 acres under vine and growing. First… Details →
Wineries Delfosse Vineyards & Winery 33 min · 23.3 mi from the house 500 DELFOSSE WINERY LANE | FABER, VA 22938 | 434.263.6100 Relax in the serene, gorgeous natural landscape of DelFosse Vineyards while enjoying our… Details →
Wineries Lovingston Winery 31 min · 22.4 mi from the house 885 FRESHWATER COVE LN | LOVINGSTON, VA 22949 | 434.263.8467 Lovingston Winery is a boutique winery located in Lovingston, Virginia. They produce a… Details →
Wineries 151 Flying Fox Vineyard 22 min · 16.8 mi from the house 10368 CRITZER SHOP RD | AFTON, VA 22920 | 434.361.1692 Amazing Rose. Their mission is to honor the emerging Virginia Wine industry with unique… Details →
Wineries Pollak Vineyards 28 min · 20.3 mi from the house 330 NEWTOWN RD | GREENWOOD, VA 22943 | 540.456.8844 Pollak Vineyards is a small family-owned winery founded in 2003 with the purchase of a 98-acre… Details →
Wineries 151 Afton Mountain Vineyards 21 min · 12.9 mi from the house 234 VINEYARD LN | AFTON, VA 22920 | 540.456.8667 Family-owned and operated winery located in Afton, Virginia. They specialize in small-batch wines… Details →
Wineries 151 Valley Road Vineyards 24 min · 18 mi from the house 9264 CRITZER SHOP RD | RAPHINE, VA 24472 | 540.456.6350 Valley Road Vineyards was established in 2015 by a group of friends from various successful… Details →
Wineries 12 Ridges Vineyard 22 min · 12.9 mi from the house 24981 BLUE RIDGE PKWY | RAPHINE, VA 24472 | 434.996.4252 A uniquely Virginian, high-elevation vineyard, tasting room, and residence club located at… Details →
Wineries 151 Cardinal Point Winery 22 min · 16.7 mi from the house 9423 BATESVILLE RD | AFTON, VA 22920 | 540.456.8400 Family-owned and operated winery located in Afton, Virginia. They specialize in small-batch wines… Details →
Wineries 151 Hill Top Berry Farm Winery & Meadery 14 min · 9.7 mi from the house 2800 Berry Hill RD | Nellysford, VA 22958 | 434.361.1266 “True to the Fruit” wines made from various fruits and authentic honey meads, crafted on a… Details →
Places to Eat Belties New Brunch Spot! Delicious food, cows out back are a hit with the kiddos! Details →
Places to Eat Black Bear Creamery 22 min · 12 mi from the house Seasonal operations. Cute spot to enjoy an ice cream treat! Indoor (with open doors) and outdoor seating available. plenty of parking. Great prices… Details →
Places to Eat Sweet Bliss Bakery This local dessert establishment prides itself on offering handcrafted desserts made from the finest ingredients. Their dedication to supporting… Details →
Places to Eat The Market at Wintergreen Resort 7 min · 2.8 mi from the house This charming market offers a carefully curated selection of gourmet foods, local produce, and artisanal goods, perfect for fueling your adventures… Details →
Places to Eat The Copper Mine Restaurant 9 min · 2.9 mi from the house More refined and sophisticated dining experience nestled within the scenic Wintergreen Resort. This just opened up after being closed for 3 years.… Details →
Places to Eat Fire & Frost 5 min · 1.6 mi from the house A cozy wood-fired pizza bakehouse in the heart of Wintergreen Resort, turning out authentic Neapolitan-style pizzas, fresh-baked pastries and morning… Details →
Places to Eat The Edge 9 min · 2.9 mi from the house One of our go-to places for a laid-back unpretentious meal. Great views if you get a booth. Offers a tantalizing menu featuring American fare,… Details →
Places to Eat Upper Crust Pizza 9 min · 2.9 mi from the house Quick, easy, low key pizza, salad + more Free Mountain Top Delivery daily from 12p-8p. Seasonal Hours Details →
Places to Eat Iron & Ale 30 min · 16 mi from the house Locals new favorite Bar+Restaurant. Many events, live music, brunch, lunch, dinner. Excellent food. Details →
Places to Eat Checkerberry Cabin A seasonal, casual on-mountain grill and event venue at Wintergreen Resort, tucked at the base of the Blue Ridge Express chairlift beside The Plunge… Details →
Hiking Hiking Master Trailfinder A custom Google Map of local trails plus a few of our favorite waterfalls — tap "Website" to open it. Trails are marked by blaze color: a fiery red… Details →
Hiking Crabtree Falls 3.6 mi · Moderate · Out & Back 3.6 Miles | Moderate | 1,135 Elev Gain | Out & Back Crabtree falls hike offers a number of great views of the waterfalls along the way as you wander… Details →
Hiking White Rock Falls Trailhead 4.6 mi · Moderate · Loop 4.6 Miles | Moderate | 980ft Elev Gain | Loop Great trail with a of open vistas, waterfalls, and narrower ethereal paths through the forest. Also a… Details →
Hiking Three Ridges/ A.T. Hike Parking 13.6 mi · Hard · Loop 13.6 Miles | Hard | 3,864ft Elev Gain | Loop If you’re more of an avid hiker you could opt to explore part of the Appalachian Trail with this… Details →
Hiking Upper Shamokin Falls and Morgan’s Loop 0.8 mi · Moderate · Loop 0.8 Miles | Moderate | 272ft Elev Gain | Loop This quick but fantastic trail is less than 10 minutes from Oak Ledge making it an ideal hike to try… Details →
Hiking Humpback Rocks 1.8 mi · Moderate · Out & Back 1.8 Miles | Moderate | 787ft Elev Gain | Out & Back Enjoy this 1.8-mile out-and-back trail near Lyndhurst, Virginia. Generally considered a… Details →
Attractions Blue Ridge Tunnel Trail, East Trailhead 4.6 mi · Moderate · Out & Back 4.6 Miles | Moderate | 370ft Elev Gain | Out & Back Although only 2.25 miles long, the Blue Ridge Tunnel Trail has plenty of wow factor. After nearly… Details →
Breweries Starr Hill Brewery 38 min · 27.3 mi from the house 5391 THREE NOTCH’D RD | CROZET, VA 22932 | 434.823.5671 Explore Starr Hill Brewery in Crozet, VA, an innovative craft brewery with a passion for… Details →
Breweries Pro Re Nata 31 min · 24.3 mi from the house 6135 ROCKFISH GAP TURNPIKE | CROZET, VA 22932 | 434.823.4878 Founded in 2015, Pro Re Nata serves hand crafted beers, local Virginia hard cider, and a… Details →
Breweries 151 Blue Mountain Brewery 23 min · 17.6 mi from the house 9519 CRITZERS SHOP ROAD | AFTON, VA 22920 | 540.456.8020 Opened in 2007 as the first brewery in Nelson County, Blue Mountain Brewery is a unique… Details →
Breweries The Brewing Tree 18 min · 13.9 mi from the house Enjoy craft beer, live music, and a family-friendly outdoor environment with plenty of seating and activities for all ages. Relax by the fire pits in… Details →
Viewpoints Blackrock Park 10 min from the house https://www.wtgpoa.org/news-updates/improvements-at-blackrock-park-amp-the-plunge-trail Blackrock Park is a newly transformed overlook offering… Details →
Viewpoints Devils Knob Overlook 6 min from the house Within Wintergreen Resort Try to always catch sunset Details →
Viewpoints 20-Minute Cliff Overlook 22 min from the house -Short Drive Stunning viewpoint nearby. A wayside exhibit shares the story behind its name: in June and July, the cliff wall below the overlook… Details →
Viewpoints Ravens Roost Overlook 19 min from the house Short drive away One of the nicest overlooks along the Blue Ridge Parkway! The parking lot is larger than almost all of the other overlooks and the… Details →
Cideries Albemarle CiderWorks 35 min · 30.3 mi from the house 2545 RURAL RIDGE LN | NORTH GARDEN, VA 22959 | 434.297.2326 Discover the charming Albemarle CiderWorks, nestled in the picturesque countryside of… Details →
Cideries 151 Bryant's Cider & Brewery 17 min · 11.7 mi from the house 3224 E BRANCH LOOP | ROSELAND, VA 22959 | 434.818.1215 Some like it dry, and some like it sweet! Our ciders range from extra dry to moderately sweet… Details →
Shopping Food Delivery Use Promo Code Below or Link for $20 off first two orders Code: DAYDC14F6 Details →
Swimming Lake Monocan Beach & Park A scenic 20-acre mountain lake about 20–25 minutes down the mountain toward Stoney Creek/Nellysford — one of the best spots near Wintergreen to cool… Details →
Swimming Rodes Farm Pool & Park Wintergreen's outdoor community pool down the mountain in the valley, set on the grounds of historic Rodes Farm beside a pavilion and park. A… Details →
Swimming Chestnut Springs Pool Wintergreen's outdoor community pool on the mountain — the closest pool to most of our homes and an easy afternoon for families. Open to property… Details →
Swimming Sherando Lake A pair of mountain lakes in the George Washington National Forest, about 35–40 minutes away — a beautiful, more rustic alternative to the resort… Details →
Distilleries Silverback Distillery 18 min · 14.1 mi from the house 9374 ROCKFISH VALLEY HWY | AFTON, VA 22920 | 540.456.7070 The only mother-daughter distilling duo in the nation, Silverback Distillery crafts… Details →
Distilleries Virginia Distillery Co. 27 min · 21.6 mi from the house 299 EADES LN | LOVINGSTON, VA 22949 | 434.285.2900 Specializing in American Single Malt whiskey, Virginia Distillery Company combines traditional… Details →
Book Direct Book Direct and Save! 3rd party verification required for all non-repeat direct bookings. 15$ Dollar Fee subject to change by provider. Details →