Holiday rentals with lake access in Wintergreen Resort

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Top-rated rentals with lake access in Wintergreen Resort

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Guest favourite

Apartment in Wintergreen Resort

4.92 out of 5 average rating, 66 reviews

Pool Access + Rainbows

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 for stone-fired pizza and beer at Fire and Frost.

Superhost

Home in Wintergreen Resort

4.79 out of 5 average rating, 107 reviews

Designer Home: A+ Views HotTub Pool GameRoom Grill

Sweeping views year round. Contemporary décor with rustic style. Retreats, romantic weekends or adventurous getaways. Close to wineries, breweries, farmers market, and hiking. 5min drive to slopes. ★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.

Superhost

Home in Wintergreen Resort

5 out of 5 average rating, 3 reviews

The Snow House Pet Friendly Creek PacMan

Escape to our peaceful 3BR/3.5Bath mountain cabin nestled in the trees along a beautiful creek—just 2 minutes from the lodge and close to scenic hiking trails. Sleeps 9–10 with a spacious layout, huge covered back porch, cozy firepit, and fun Pac-Man arcade machine. Enjoy a brand-new kitchen with 2 dishwashers, full laundry, and plenty of space to unwind. Pet-friendly and perfect for families or groups seeking comfort, nature, and connection. 3 pools, 3 golf courses, tennis, pickle, archery etc

Guest favourite

Cabin in Nellysford

4.96 out of 5 average rating, 222 reviews

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.

Top guest favourite

Yurt in Afton

5 out of 5 average rating, 923 reviews

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!

Top guest favourite

Cabin in Wintergreen Resort

4.88 out of 5 average rating, 129 reviews

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!

Top guest favourite

Home in Nellysford

4.99 out of 5 average rating, 143 reviews

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!

Top guest favourite

Guest house in Massies Mill

4.99 out of 5 average rating, 84 reviews

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.

Top guest favourite

Apartment in Wintergreen Resort

5 out of 5 average rating, 242 reviews

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!

Top guest favourite

Home in Wintergreen Resort

5 out of 5 average rating, 12 reviews

FamilyFriendly-Pets-HotTub Gameroom-Firepits-Grill

Bring the whole family to this warm mountain home! Welcome to Whitetail Lodge, a well designed home in the heart of Wintergreen. A perfect spot for groups or families, with tons of games, record player, kids teepee tent area, two fire pits, lots of areas to spread out, and multiple outdoor seating areas. With 5 bedrooms total, a full loft, plus a downstairs living room, bunk room, and game room, there is plenty of room for up to 14 guests and it is pet friendly!

Guest favourite

Cabin in Faber

4.97 out of 5 average rating, 124 reviews

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.

Guest favourite

Home in Roseland

4.95 out of 5 average rating, 22 reviews

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.