Apartment holiday 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.

4.99 out of 5 average rating, 103 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!

4.75 out of 5 average rating, 510 reviews

The exterior features a two-story home with a welcoming red front door. The entrance is accessible by a wooden staircase, surrounded by a deck and landscaped with trees and fallen leaves. A paved driveway accommodates parking for multiple vehicles.

Flat in Waynesboro

Spacious lower level Airbnb! READ SUMMARY!

Hello everyone! I’m not going to try to convince you to stay at this Airbnb but instead address the issues that guests have complained about in reviews. This listing is priced accurately and cheap because there isn’t much besides 2 king beds, bathroom, washer/dryer. There is a bit of noise from upstairs when people walk around but usually no later than 11 PM. Please keep in mind when reviewing that you’re not paying very much to stay here. If you’re going to complain, please stay elsewhere.

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.

4.98 out of 5 average rating, 177 reviews

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.

4.86 out of 5 average rating, 79 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!

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.

4.78 out of 5 average rating, 854 reviews

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.

A panoramic view of rolling mountains is displayed under a colorful sky during sunrise. Soft clouds hover over the lush green hills, creating a serene landscape. The vast expanse of nature invites tranquility and offers a sense of openness.

5 out of 5 average rating, 11 reviews

Family and dog friendly with views and pools!

2 bed/2 full bath renovated condo at the Overlook! Dog friendly! This beautifully renovated condo is appointed with 1 king bed, 1 queen bed and an olympic queen sized sleeper sofa + pack-n-play - it is ideal escape for a couples getaway or a family vacation! Enjoy a great view of the fireworks from the balcony to ring in the New Year or to celebrate our Independence Day. There are legos, magnatiles, children’s books and a rotating assortment of other kids toys to keep kids entertained

4.98 out of 5 average rating, 207 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.

Flat 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 Fire & Frost eatery and the Wintergreen Spa, this is an ideal location.

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, 38 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, 105 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.

The exterior of a bright red barn-style building is showcased, featuring large windows that allow natural light to enter. A well-maintained lawn with small shrubs enhances the landscaping, while a staircase leads up to the entrance. The inviting setting is complemented by a clear blue sky.

4.99 out of 5 average rating, 520 reviews

The Barn at Haden near Wineries and C'ville

The Barn at Haden is a custom well appointed finished 2 bedroom, 1 full bath space elevated above a detached 3 car garage with a large outdoor private deck. It features a fully equipped gourmet kitchen with high end finishes. Whether staying for a night or for the weekend, it is an experience to enjoy the easy living Crozet has to offer. Walkable/bikeable to downtown Crozet, 2 miles to King Family Vineyard & Chiles Peach Orchard and 15 minutes from Charlottesville.

5 out of 5 average rating, 6 reviews

The highland hideaway

Welcome to our mountain retreat! Conveniently located near the Wintergarden Spa , the Nature foundation and numerous trails , our place is great to relax after skiing or to just be in the midst of nature or discover one of the many wineries and breweries nearby. 2 bedrooms : one with a queen bed and the second with a full bed . 2 bathrooms both with tubs . A fully equipped kitchen and a cozy living room with fireplace.

A warm and cozy bedroom is visible, featuring a spacious bed with yellow pillows and a neutral quilt. A bedside table holds a ceramic cup and a small lamp with a textured shade. Soft lighting enhances the inviting atmosphere against wooden accents and a colorful area rug.

4.78 out of 5 average rating, 102 reviews

Earth Room Suite | Quiet Blue Ridge Retreat

Find peace at Galleywinter Farm’s cozy farmhouse retreat in the Blue Ridge Mountains. Enjoy the entire private ground floor with its own entrance, rustic bathroom with Jacuzzi tub, and patio overlooking the woods. Guests love the calm, cozy energy—many say it’s the best sleep they’ve ever had. Relax in the sauna, forest bathing tub, or yoga studio and reconnect with nature in this healing, restorative space.

Popular amenities for Wintergreen Resort apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

A spacious living room is displayed with a gray sectional sofa and an additional gray couch. A wooden coffee table is positioned in front of the seating area. Large windows provide natural light and views of the surrounding mountains. A flat-screen TV is mounted on the wall.

4.71 out of 5 average rating, 48 reviews

Piedmont Place 304| Lux Vineyard & Brewery Getaway

A bright efficiency apartment is showcased, featuring a spacious bed with soft linens and decorative pillows. A small dining table with four chairs is positioned nearby, and a kitchenette with a microwave and coffee maker is visible. Light enters through two windows, enhancing the airy feel.

4.87 out of 5 average rating, 359 reviews

Best Spot on the Wine/Brew Trail!

Flat in Waynesboro

New place to stay

Cozy Waynesboro Retreat w/ Patio & Washer/Dryer

A modern kitchen features white cabinetry with granite countertops. A large window allows natural light to brighten the space. Pendant lights hang above, while stainless steel appliances include a refrigerator and a professional-grade stove.

4.83 out of 5 average rating, 23 reviews

Lux 2 Bed 2 Bath Apt | Dwtn Crozet (30 Nt Min)

An open living and dining area is visible, featuring a comfortable gray sofa and a wooden dining table with multiple chairs. Light hardwood flooring extends throughout. A modern kitchen is partially seen in the background, with contemporary appliances and a small unobtrusive rug underfoot.

Flat in Stuarts Draft

4.22 out of 5 average rating, 9 reviews

Sun Outdoors Shenandoah Sandstone Lodge

A cozy living area is present, featuring a spacious sectional sofa adorned with colorful throw pillows. A coffee table is positioned centrally, and a large flat-screen television is mounted on the wall. Natural light streams through expansive windows, highlighting the warm wood accents.

4.8 out of 5 average rating, 5 reviews

Slope-Side with a Mountain View

A comfortable living area features a light-colored, spacious sofa positioned against a softly lit wall. A small dining table with black chairs sits nearby, complemented by a kitchenette equipped with modern appliances. Soft carpeting covers the floor, adding to the inviting atmosphere.

Flat in Waynesboro

4.86 out of 5 average rating, 7 reviews

Valley retreat

The modern living area features a light-colored sofa, a minimalist coffee table, and a round accent table. Soft lighting hangs above a sleek kitchen with stainless steel appliances. Large glass doors invite natural light and provide access to a balcony with outdoor seating.

4.81 out of 5 average rating, 59 reviews

Piedmont Place 301| Lux Vineyard & Brewery Getaway

Private apartment rentals

The living area features a leather sofa, a glass coffee table, and a wall-mounted TV. Natural light floods through two windows, enhancing the space. A dining table with four chairs is positioned nearby, and a fireplace adds a cozy touch to the room.

4.75 out of 5 average rating, 4 reviews

WalktoSki&Resort/Spacious/PupsWelcome!

4.96 out of 5 average rating, 50 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.

Flat in Tyro

Crabtree Falls Mountain Hollow Guesthouse

The living room features a spacious seating arrangement with two sofas, a cozy armchair, and a round coffee table. Large windows frame expansive views of the Blue Ridge Mountains, inviting natural light into the airy space. A dining table for six is visible in the background.

4.93 out of 5 average rating, 45 reviews

Big Condo*Luxe Baths*Sweeping Views*Walk2Chairlift

A modern living area is highlighted by a spacious gray sectional sofa adorned with patterned throw pillows. A round black coffee table sits nearby. The kitchen features white cabinetry and a sleek dark countertop, with three wooden bar stools positioned at the island.

4.91 out of 5 average rating, 33 reviews

Piedmont Place 401| Lux Vineyard & Brewery Getaway

The green exterior of a spacious house is surrounded by trees and gently rolling hills, showcasing a panoramic view of the Blue Ridge Mountains in the background. A well-maintained yard is visible, with landscaped gardens and a gravel driveway leading to the entrance.

Luxury Guest Quarters w/Blue Ridge Mountain Views

A welcoming living space features a gray couch adorned with orange and decorative pillows. A wall-mounted TV is positioned above a faux fireplace, complemented by a glass coffee table. A green accent wall and a patterned rug add character to the area, with wooden shelves displaying various items.

5 out of 5 average rating, 43 reviews

Mtn Vineyards Getaway

4.9 out of 5 average rating, 10 reviews

Eagles Court Ski In/Out Condo

5 out of 5 average rating, 52 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.

Flat in Lovingston

Loft w/ Private Covered Heated Pool

Apartment rentals with a hot tub

4.82 out of 5 average rating, 72 reviews

An exterior view of the property's side shows a sturdy gray house with stone accents. A covered area features a hot tub positioned next to the entrance. The gravel driveway extends, leading toward a scenic landscape with trees and a fence in the background.

Flat in Monroe

Bear Mountain Farm

4.9 out of 5 average rating, 147 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.

Flat in Lovingston

Lovingston Get-Away Lovingston, VA

A spacious room features a queen walnut bed with a wooden headboard. Natural wood accents enhance the warm atmosphere. A kitchenette area holds a microwave and a small refrigerator. A large stone arch window offers a view of the outdoors, and a cozy armchair is positioned beside a lamp.

4.73 out of 5 average rating, 806 reviews

Suite Pea at White Lotus Eco Spa Retreat

Private room in Stanardsville

A spacious communal area features wooden beams and a polished concrete floor. Large windows allow natural light to fill the space, highlighting a long dining table and cozy seating arrangements. Two distinct levels create an open, airy atmosphere, ideal for gatherings.

4.67 out of 5 average rating, 149 reviews

Crows Nest at White Lotus Eco Spa Retreat

The spacious room features a large bed with soft bedding, complemented by bedside lamps. A comfortable seating area is positioned nearby, and natural light enters through a window, creating a bright atmosphere. Access to a private balcony with seating is visible in the background.

4.77 out of 5 average rating, 555 reviews

Balcony Suite at White Lotus Eco Spa Retreat

The spacious room features a cozy layout with reclaimed wood shelves storing dishes and utensils. A compact refrigerator and microwave are visible, along with a flat-screen TV mounted on the wall. An elegant archway provides access to the sleeping area, which includes a queen bed.

4.71 out of 5 average rating, 569 reviews

Royal Suite at White Lotus Eco Spa Retreat

4.85 out of 5 average rating, 33 reviews

An inviting great room features wooden flooring and soft blue walls. A comfortable turquoise sofa and matching chairs are arranged around a coffee table. A television stands on a cabinet, with natural light streaming in from windows, leading to a master bedroom visible in the background.

Flat in Charlottesville

UVA Neighborhood Spacious Upper Floor

A spacious bedroom features a king-size hand-carved Balinese wood bed with soft grey bedding. Light wood walls and a pine ceiling create warmth. Two bedside lamps provide ambient lighting, while a round mirror and a small side table add a touch of elegance.