Holiday rentals with lake access in Wintergreen Resort

5 min toSki! Mntn View HotTub Pool Table MovieRoom

5min drive to slopes. Sweeping views year round. Contemporary décor with rustic style. Retreats, romantic weekends or adventurous getaways. Close to wineries, breweries, farmers market, and hiking. ★3,500sqft on 3 floors ★Hot tub for 8 people ★Sound system ★2-Story vaulted ceiling, gas fireplace, 55” TV ★Movie room: 65” TV, pool table, wet bar, wine fridge ★Dining table seats 10 ★Desk and FAST WiFi ★Roku TV in every bedroom ★Park 6 cars Seasonal outdoor pool/tennis. Resort access not included.

2 Fireplaces + Amazing Views

Wake up to awesome views and coffee by the fire. This unit is perfectly situated at The Ledges, just a quick five-minute drive to the Mountain Inn. Mountain Dreams is a newly designed, phenomenal condo that offers stunning 180-degree views of Charlottesville, Lake Monocan, the UVA observatory, and ski slopes. Located at the highest elevation, this two-story condo provides a prime location, only 8 miles from Devils Backbone Brewery, Bold Rock or Three Notch'd. Walk conveniently across the street

Tiny Luxury Retreat: Lake, Hikes, Brews & Vines

Welcome to our luxurious tiny house nestled in the heart of Nelson County, Virginia. This enchanting retreat, surrounded by the majestic Blue Ridge Mountains, offers an unparalleled experience in a landscape dotted with wineries, breweries, distilleries, and sprawling farmland. This luxury tiny house was built in 2022 and is available for couples, solo travelers, or a small family wanting to explore this beautiful stretch of the Blue Ridge Mountains. FREE Electric Vehicle Charger on-site.

Luxe Yurt w/Hot Tub in the Heart of the Blue Ridge

Experience glamping, Blue Ridge style. Our luxury yurt is located at the top of a small hill, in the center of a 70 acre farmstead surrounded by natural beauty. Night Archer Farm is located off a quiet country road in Afton, Nelson County. It is private, but not remote. You are close to the Brew Ridge trail, wineries, breweries, skiing at Wintergreen, Blue Mountain Brewery, Devil's Backbone, golf, hiking, or driving the Blue Ridge Parkway. Hike directly from the Yurt up into the mountains!

The Bear Dance Cabin at Wintergreen Resort

Tucked back in the woods in the Wintergreen Resort, we're on the top of Wintergreen Mountain, elevation just under 4k, near all the resort's amenities. Our family built on Wintergreen Mountain after learning how unique and beautiful the seasons are here. The cabin quickly became a new member of the family and we can’t imagine not having her in our lives now. Ten years after building we decided to provide short term rental and the experience has been beyond what we had ever imagined. Enjoy!

151Escape | 5☆ Group Fun! Game Room/Bar/Deck/4kTVs

Enjoy mountain adventures with friends & family at this beautiful & newly renovated 5 bedroom mountain house ideally located in Virginia Wine Country at Wintergreen Resort’s Stoney Creek valley area. This amazing home features: - 75” & 55” 4k TVs - Fully equipped, live edge wet bar & bar countertop - Professional Ping Pong table - Deck with views, firepit & grill Just minutes from skiing, golf, hiking, wineries, breweries, apple-picking and other adventures the area offers all year long!

Solar-powered Guesthouse at Peak Time Property

This cozy guesthouse is a perfect getaway. It has SPECTACULAR views of the Priest and Three Ridges. Located in Massies Mill, it is a 20-30 minute drive to the Appalachian Trail, Wintergreen, breweries, wineries, and distilleries. It is also practically around the corner from Pharsalia Events. There are several convenience stores close by, but the closest grocery store is an 18 minute drive. Situated on 26 acres, there is more than a mile of marked trails available to walk as you wish.

Sunset Vista Mountain Views “Skies for Miles”

Welcome to Sunset Vista Villa, where you enjoy, “Skies for Miles.” This beautiful, 2 bedroom, 2 bath, first-floor-unit with second story mountain views, is near all amenities the Wintergreen Resort has to offer. It comfortably sleeps five and with its western vistas, sunsets are a thing to behold! Whether you spend your days hiking, skiing or enjoying the wineries and breweries, SVV will enhance your stay. Book today & come enjoy the Wintergreen Resort and Blue Ridge Mountains!

Luxury Lodge: Stunning All-Season Views! Sleeps 14

This is a Wintergreen Oasis, with four-season views at one of Wintergreen's finest homes! Luxury, 5B/4.5B home in Wintergreen Mountain Resort Village. Built on top of the Black Rock Mountain with incredible year-round views Of Devil's Knob Mountain and the Blue Ridge Mountains. The floor plan is made for entertaining with friends, families, or well suited for your corporate getaway. Come relax at Big Black Bear Lodge and enjoy the best of what this area has to offer.

Minutes to Ski Lodge/HotTub/GameRoom/FirePit

Welcome to The Moose Lodge, a rustic Wintergreen Resort ski chalet located .5 miles from Mountain Inn, where you’ll find the main ski lodge, equipment rental center/ski lift and several dining options. Amazing 2-story stone gas fireplace and a fully equipped chef’s kitchen. Relax around the propane fire pit or unwind in the hot tub on the back deck. Minimal steps down into the home from the parking area. Game room w/ pool table, games and a 50" Smart Roku TV.

Hot Tub@ Lakefront Cabin w Stunning Curated Decor

✨ A Marvelous Night for a Moondance Awaits ✨ Welcome to Moondance—a lakeside log cabin with serious style and mountain soul. Designer interiors, cozy fireplaces, an après-ski game room, and dreamy views set the stage. Whether you're sipping wine on the deck or roasting s’mores under string lights, this is where memories are made. Minutes to wineries, Wintergreen, and the Blue Ridge Parkway. Relax, reconnect, and maybe do nothing at all. We support that.

Hot Tub! Wintergreen Resort!

Prepare to escape and relax at our three bedroom, two bath cabin, nestled atop the Blue Ridge mountains. This luxury resort retreat is perfect for couples getaway, wedding, family vacation or girls weekend. Spend the day brewery hopping down the famous Route 151, where you have over twelve wineries and breweries to visit. Or enjoy hiking, skiing, spa & golfing. Swimming pool access at Chestnutt Springs and Rhodes farm between the hours of 2pm and 8pm.