Vacation rentals with a patio in Wintergreen Resort

Cozy Mountain Cottage on Brew/Wine Trail-King Bed

Welcome to the Sugah Shack, a cozy, beautifully appointed new construction cottage nestled in the foothills of the Blue Ridge Mountains! Located midway on the Brew Ridge Trail, but 500 yards off the byway, so guests have a quiet retreat. Perfect for romantic getaways, destination telework space, or families exploring this outdoor paradise community. Stunning property boasts beautiful vistas with sweeping 300-degree mountain and a year-round calendar of outdoor activities. GAS FIREPLACE/FIREPIT

Tips Up: Cozy Slopeside Retreat w/ Fireplace

The mountains are calling and you must go. Well, you don't have to, but we think it's a good idea. Make Tips Up your home while you're away. With slopeside views, a cozy and comfortable ambiance, and close proximity to skiing (only 100 yards from the slopes!) and hiking, this 1B/1BA condo is the perfect getaway for outdoor enthusiasts seeking a mountain escape. Relax at nearby breweries and wineries with unbeatable views, and return to your condo to enjoy the amenities of Wintergreen Resort.

Cozy Log Cabin

Relax and unwind in this secluded, hand-hewn log cabin with all the modern conveniences. 10 minutes off the Blue Ridge Parkway from mile marker 16, minutes from Shenandoah National Park and the Appalachian Trail, close to 4 breweries, 6 wineries, 3 cideries, and Wintergreen Four-Season Resort. Located on over 300 acres of private land with plenty of room to explore and enjoy the wildlife. Come witness the brilliant night sky lying in an open field with no city lights to diminish the experience.

Bear Creek Inn

You will be renting the 2 bedroom cottage, optional 3rd bedroom, very large, fenced yard for your pet. Relax at this quiet, peaceful place with year round trout stream. Minutes from the breweries and wineries on Nelson 151. Plenty of outdoor activities to enjoy. The George Washington National Forest is across the street for exploring, hiking and hunting. The house is only 4 miles from Crabtree Falls and several minutes from the Appalachian Trail access. Wintergreen Resort is 12 miles away.

Ridge Top Contemporary Cottage-Inspiring Mt. Views

Modern studio cottage in stunning mountain setting. Feels like your own mountaintop treehouse retreat, yet is only a few miles from Nelson County amenities: wineries, breweries, hiking trails, restaurants, and coffee shop are a short drive down Route 151. The cottage is 465 sf with a wraparound deck adding 450 sf. High ceiling with a wall of windows offering mountain views in every direction. Luxury king sized bed. Newly redesigned smooth and EZ entry road for all cars as of May, 2024.

2-min drive from hiking/resort, seasonal HOA pool

Peaceful, newly renovated mountain-top retreat. Relax or work from home. End your day with a hike or personal spa treatment before you linger with a glass of wine over an amazing view at sunset. It’s only a 2 minute walk from the front door. Welcome to our mountain home! 2-3 min drive from ski lifts/resort, hiking Free firewood (seasonal) Family games & smart TVs (no cable) for movie night (must sign into your own subscriptions) Smartlock entry Stair-free entry *outdoor pools CLOSED

Inn at the Woods: Updated Cabin w/Mountain Views

Fall in love with the charm of this recently updated ‘Hansel & Gretel’ style cabin located on Castle Rock Mountain. This cabin has 3 bedrooms + a loft, with a total of 4 queen beds. Hike and explore the 20+ acres or relax on the large multi-tiered deck and fire-pit area while soaking in the mountain sunsets. Enjoy nearby dining, breweries, or wineries, the historical town of Charlottesville, or spa, golf, tennis, and skiing at the Wintergreen Resort - both just a short drive away.

1 bedroom condo, hiking, breweries, wineries

Enjoy the mountains in the spring & summer enjoy hiking or a swim in the heapool! 1BR 1BA centrally located in Wintergreen 5 minute walk to Wintergreen resort Close to many hiking trails Enjoy the many breweries & wineries in the area Mountaintop Market is across the street 1 Bedroom 1 Bath & New queen sleeper sofa Stocked kitchen, cookware, spices & cooking oils Premium coffee & assorted tea Private furnished patio Wood burning fireplace, all you need for a quiet getaway

Luxury Lakefront Cabin w/Fire Pit & Stunning 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.