Apartment holiday rentals in Charlottesville

Panoramic Sunsets, Mountain Views, Private Deck.

Wake up above the mountains and end your day with unforgettable sunset views some of the best on the mountain. Sunset Vista Villa is a cozy retreat designed for slowing down, morning coffee on the deck, evenings by the fire. With two private bedrooms, each with its own en-suite bathroom, its perfect for couples or friends. Easy entry with just a few steps, yet elevated views make this stay both convenient and special. Ask us about early check-in or late check-out to enjoy even more of the view

Five Minute Walk to Everything!

**Pet friendly** two bedroom, two bath, loft style condo centrally located at Wintergreen Resort. Ski check-in/lifts, restaurants, the mountaintop provisions market, and the Mountain Inn and conference center are all within a 5 minute walk! This is a two-story unit with loft style bedroom and en suite bath, and first floor bedroom with hall bath. Parking, pool access, washer/dryer, and Wi-Fi included. Fully stocked kitchen, wood burning fireplace, balcony, all towels/linens provided. Sleeps 5.

Luxury Condo in the Sky! Finest in Wintergreen!

Welcome to our recently renovated luxury condo in the sky! Perched on the edge of the Wintergreen ridgeline, we are just a stone’s throw from nature’s bounty. Our condo offers the perfect blend of relaxation and access to recreation. Hit the ski slopes, take a hike, or explore the bountiful brew and wine scene and then come enjoy the view. The horizon is 75 miles distant from our balcony on a clear day! We love hosting families with kids or couples coming to enjoy all that Wintergreen offers!

The Townie 3 BD/2BA Historic Downtown Building

Three bedroom/ two bathroom apartment in a 1940s building located in the heart of Charlottesville, just off the Downtown Mall. Brightly lit large space with charm and comfort, including full kitchen, wifi, living room w/ smart TV, hardwood floors throughout, blackout curtains, laundry in unit. Your group will enjoy easy access to everything - walk score 100! Three queen beds + living room sofa + air mattress. Pet friendly with extra fee. Each bedroom has blackout curtains for comfort.

Eight Minute Walk to Everything

This one-bedroom, one-bath condo is centrally located. Ski check-in, restaurants, the mountaintop provisions market, and the Mountain Inn and conference center are all within an 8 minute walk. It's a one-story, downstairs unit that includes a back porch with just a few steps down to the ground. Perfect for taking the dog outside in the pet-friendly space. Full kitchen and dishes, wood-burning fireplace, balcony, and all towels and linens are provided for your convenience. Sleeps 3.

3 BR 3 BA, 2 story condo in Highlands

Newly renovated condo! You can't beat the view from up here. Top floor/vaulted ceilings, next to the Highlands Lift. Just steps from the expert slopes and on the Wintergreen shuttle route. Enjoy hiking, skiing, snowboarding, tubing, outdoor pool time or a local brewery. This condo has 2 master's with king beds, 1 bunk bed (twin over full), a single twin bed and a pull out twin sleeper sofa. The king beds have new high quality mattresses and luxury bedding and a 60" HDTV in living room

1 bedroom condo, close to hikes & breweries & pool

Cozy 1BR Wintergreen condo 🌳 🌄 Close to scenic hikes, local breweries and wineries. The resort village, and mountain-top market, just minutes away. Enjoy a fully stocked kitchen, premium coffee and teas, cooking oils and spices. Relax after a day outdoors and enjoy a smart TV, fast WiFi and games. Comfortable queen bed in the bedroom plus new queen sleeper sofa in the living room. Private furnished patio with peaceful wooded views and or cool off in the heated community pool.

Ski-In Ski-Out ~ Mtn Views ~ King Suite

Just steps from Wintergreen Resort’s slopes, Slope Side Gem offers the perfect mountain escape! Located in the heart of Mountain Village next to the Mountain Inn, you’re just a short walk to Starbucks, The Market, shops, and three restaurants and bars. Whether you’re skiing, hiking, golfing, or enjoying a local brewery or winery, adventure is at your doorstep. After an exciting day, unwind on the private balcony and take in the breathtaking mountain views!

Wintergreen Resort King bed, Fire place, 2 Bd/2 Br

Forget your worries in this spacious and serene space. Condo has been completely renovated and can be enjoyed all year round! Located between the Wintergarden Spa, the Nature Foundation and the Devils Knob Sports Center (golf, tennis and fine dining restaurant) Stone Ridge neighborhood is centrally positioned to most of the Resort amenities. 5 min drive to slopes 5 mins to Market 15 to Devils Backbone 3 mins to Devils Knob golf course

Cozy Laurelwood condo - 10 min walk to slopes

This beautiful 1-bedroom, 1-bath Laurelwood condo is perfectly located just a short walk from the pool, market, coffee shop, restaurants, and the Wintergreen Conference Center. Inside, you’ll find a fully equipped kitchen, a cozy wood-burning fireplace (with complimentary firewood), and a spacious king-size bed. Step outside to your private deck and enjoy the peace of the surrounding forest—an ideal retreat for relaxation and comfort.

Condo at Wintergreen

You don’t want to miss these views! Come enjoy the breathtaking fall foliage in cozy comfort. Our 2 bedroom condo offers central access to dozens of wineries, breweries, and restaurants as well as being in short driving distance to Charlottesville and Shenandoah national park! Miles of available hikes await for you in the resort or venture further out to explore the mountain and waterfalls nearby!

The Modern Mountain Condo

Nestled inside Wintergreen Resort, this freshly updated condo is a quiet retreat with mountain views and easy access to hiking, skiing, wineries, breweries, restaurants, and antique shops. Inside, you’ll find an open, light-filled layout with a wood-burning fireplace, full-sized appliances, and ample cabinet space. Step outside to your private patio or take a dip in the community pool.