Apartment vacation rentals in Wintergreen Resort

A balcony is featured, showcasing two Adirondack-style chairs positioned for optimal mountain views. Sunrise illuminates the expansive horizon, with soft light reflecting off the distant landscapes. The floor is made of wood, enhancing the outdoor ambiance.

5 out of 5 average rating, 98 reviews

Endless Mountain Top Views from All The Way Up!

Our warm and inviting condo combines amazing proximity to hiking with to-die-for views of the Blue Ridge Mountains and the horizon 75 MILES distant! Our condo sits a mere 400-yd walk from the closest hiking trail and also has direct access to the ridge line walking area - perfect place for a morning stroll! This updated and modern mountain themed space features: ✸ Newly renovated! ✸ Stocked modern kitchen! ✸ Two full bathrooms! ✸ Helix Hospitality Mattresses!! ✸ Cozy Fireplace w/ wood provided!

A cozy living area features a stone fireplace with a wooden mantle. Natural light enters through large windows framed by light curtains. Comfortable seating includes a brown sofa with decorative pillows and a stylish orange chair. An adjacent dining table offers space for meals.

5 out of 5 average rating, 13 reviews

3 Ridges 3 min walk to slopes,besides inn,King bed

Best of Wintergreen located in beautiful three ridges community, great location besides Wintergreen Inn, Parking in front of condo, short 3 min straight walk to the slopes , all in walking distance, enjoy garden ground level from your beautiful terrace, peacefull and private, Master bedroom with memory foam King Bed, Comfortable queen Sofa bed, granite kitchen, Central a/c cold and heat,hot water,wifi,TV with netflix,Keurig machine, regular coffee maker, Check in and out Time Flexible Please ask

4.98 out of 5 average rating, 172 reviews

Rolling green fields are framed by colorful trees in autumn hues, creating a serene landscape. Horses are seen grazing near a small shelter, with distant hills providing a picturesque backdrop under a soft sky.

Apartment in Afton

Cozy stay with scenic views on a horse farmette

Cozy apartment with beautiful views on a horse farmette on the most scenic road in the county. Located within 15 miles from Charlottesville and only 6 miles from Shenandoah National Park and the Blue Ridge Parkway, this vacation rental is the perfect spot if you are looking for places to hike, scenic drives or visit the many wineries, breweries or cideries located in close proximity. The apartment is situated over the garage and has its own separate entrance offering guests plenty of privacy.

The living area features a comfortable sectional sofa and a wooden coffee table, with a visible fireplace centrally located. Large windows provide natural light and views of the outdoor space. A mounted television is positioned above the fireplace, complementing the cozy ambiance.

4.88 out of 5 average rating, 73 reviews

Wintergreen Getaway

Relax with the whole family at this peaceful place to stay. Enjoy morning coffee and evening cocktails on the deck fronting the golf course. You will love the location and features! Walking distance to spa, The Wintergreen Nature Foundation, and Fire & Frost. Convenient to slopes, Chestnut Springs pool and Upper Shamokin Falls. A great place to relax after a full day of hitting nearby slopes or hiking trails, and exploring Nelson 151's winery and brewery attractions. Stairs to access. WiFi!

4.77 out of 5 average rating, 848 reviews

A spacious studio features a queen-sized bed with crisp white linens and decorative blue pillows. Natural light filters through sheer curtains, illuminating the room. A small artwork in blue hangs above the bed, complemented by bedside lamps. A minimalist table is positioned at the foot of the bed.

Apartment in Afton

Studio Apt. in Wine/Brewery Country/on 151

Clean & bright studio apartment with full kitchen & full bath. Less than 1 mile from Blue Mt. Brewery and Flying Fox Vineyard. Cardinal Point Vineyard, Afton Mountain Vineyard, Silverback Distillery, Valley Road Vineyard & Veritas Vineyard all between 2-5 miles away. Right on 151 also known as "alcohol alley". Tons of breweries, distilleries, ciderys & vineyards all up and down the road. The setting is peaceful. Apt. has fiber internet and Apple TV. Pets welcome for 30 dollars per pet.

4.9 out of 5 average rating, 144 reviews

A wooden deck is elevated and features a vibrant red umbrella. Surrounding the deck are leafy green plants and a small seating area with pink chairs. A lattice design is present under the deck, adding texture to the space.

Apartment in Lovingston

Lovingston Get-Away Lovingston, VA

Guesthouse for ADULTS ONLY/ NO kids/pets located in Lovingston, VA. There are wineries, breweries, and distilleries. We have the Wintergreen Ski Resort. The Music Festival in October. Crabtree Falls and Humpback Rock for hiking. In Nelson Co., the Blue Ridge Parkway and Skyland Drive began. Nearby is UVa's Rotunda, Monticello, Appomattox, DC, Schuyler (the Waltons). Nelson hosts peach and apple festivals each year. The beautiful foliage to be seen in the fall and winter snowy mountains.

4.96 out of 5 average rating, 45 reviews

A craftsman-built apartment is nestled among lush greenery, surrounded by mountain forests. Vibrant flowers frame the foreground, leading to the wooden structure with a metal roof. The natural landscape features rolling hills and a clear blue sky, creating an inviting outdoor setting.

Apartment in Tyro

Crabtree Falls Mountain Hollow Guesthouse

Get back to nature in a river front apartment nestled in the Blue Ridge Mountains. Adjacent to the owner's home, above a rarely used garage, the 70-acre well-maintained property offers mountain forests and a pond view with outdoor experiences for star gazing, and campfires. Escape electronic devices to explore area attractions, waterfalls, hiking trails, scenic drives, and fishing. This new rental is craftsman built with wood interior. We also love hosting our other cabin, Parr's Camp.

An outdoor dining setup on a spacious deck features several plates with a breakfast spread, including eggs, fruit, and pastries. A steaming cup and a glass of juice are present. In the background, a telescope is positioned to enjoy the scenic mountain view under a cloudy sky.

4.97 out of 5 average rating, 35 reviews

Luxury Condo: Stunning Slope Views, Sauna, Dogs-Ok

Welcome to the view from above the clouds! Our two-floor penthouse condo right on the ridge at Wintergreen Resort has stunning views of the mountains and ski slopes. On warm days, you can soak in the sun and dine al fresco on the enormous wraparound deck. On chilly nights, there’s a wood-burning fireplace for cozying up. And no matter the weather, you can soothe your muscles in the state-of-the-art infrared sauna. Whether you’re looking for peace or adventure, this is the place!

A table set for two features a bottle of sparkling beverage and two glasses, accompanied by an elegant plate of appetizers. The backdrop showcases expansive mountain views under a bright sky, enhancing the serene atmosphere of the outdoor dining area.

4.97 out of 5 average rating, 99 reviews

Mountain View Nest

From the moment you walk in, this condo offers endless opportunities to relax and retreat. The sweeping mountain views over the back deck provide the ideal setting for a romantic getaway, a girls weekend, or much needed time to recharge. This one bedroom/bathroom unit with a king sized bed, fully stocked kitchen, and artistic decor is located on the third floor of the Ledges. It is the perfect location for those who ski, hike, golf, or taste the flavors from local wineries.

4.98 out of 5 average rating, 199 reviews

A bright and airy living area is highlighted by large windows offering mountain views. A casual seating arrangement features a light-colored sofa and a wooden dining table surrounded by black chairs. Sliding glass doors provide access to an outdoor deck.

Apartment in Rockfish

Blue Ridge Bliss - For family & friends to enjoy!

Welcome to Blue Ridge Bliss! Come enjoy the mesmerizing mountain top views of this well-appointed condo in The Ledges of Wintergreen Resort. It’s the perfect place to unwind, unplug and recharge. Whether here to ski, hike, or visit Virginia wineries, cideries, or craft breweries you’re sure to enjoy the beautiful views from the living room and deck. A short walk to The Highlands lift and across the street from the dog park, and picnic area it’s an ideal location.

5 out of 5 average rating, 48 reviews

A private heated in-ground pool is set within a fenced area, complemented by wooden lounge chairs arranged around the poolside. Sunlight illuminates the clear blue water, while trees surround the space, providing a natural backdrop and a sense of privacy.

Apartment in Lovingston

Loft w/ Year-Round Private Covered Heated Pool

Sneak away to this cozy mountain loft—your perfect couples’ retreat in Virginia’s wine and beer country. Just off Route 29, you’re minutes from vineyards, trails, and local brews. The space is clean, comfy, and made for easy, no-stress stays. Cool off in the private pool (shared with one cottage), then sip something local as the sun sets. Quiet, cute, and calling your name. Need more room? Check out our cottage for up to 6: airbnb.com/l/i33AHeKs