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Condo holiday rentals in Shenandoah Valley

Find and book unique condos on Airbnb

Top-rated condo rentals in Shenandoah Valley

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Top Guest favourite
The exterior of a multi-level building is showcased against a clear blue sky. Natural stone surfaces and wooden decks are visible, surrounded by leafless trees. A walking path leads to the entrance, enhancing accessibility to this mountain retreat.
Condo in Wintergreen Resort
4.99 out of 5 average rating, 268 reviews

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

Top Guest favourite
The two-story condo features a warm wood exterior, framed by lush greenery and trees. Wide wooden steps lead to the entrance, giving access to individual balconies that enhance the inviting appearance of the building.
Condo in Wintergreen Resort
4.96 out of 5 average rating, 350 reviews

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.

Top Guest favourite
The living area features large sliding glass doors that open to a stunning view of the mountains. A modern dining table is positioned nearby, illuminated by a pendant light. Comfortable seating is arranged around the room, enhancing the inviting atmosphere.
Condo in Wintergreen Resort
4.98 out of 5 average rating, 124 reviews

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!

Top Guest favourite
The exterior of a two-story cabin houses warm wooden accents and large windows. The entrance features a welcoming set of wooden steps leading up to a balcony, surrounded by tall trees, with a concrete pathway leading toward it.
Condo in Wintergreen Resort
4.94 out of 5 average rating, 247 reviews

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.

Top Guest favourite
A scenic view of rolling hills is captured at sunset, with soft hues of orange, pink, and purple coloring the sky. In the foreground, a glass of clear liquid rests on a wooden railing, enhancing the tranquil atmosphere.
Condo in Wintergreen Resort
4.99 out of 5 average rating, 180 reviews

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

Guest favourite
A private furnished patio features a cozy seating area with light-colored cushions on a dark frame sofa. A wooden coffee table sits in front, accented by a woven rug. The surrounding greenery adds a natural backdrop, creating a peaceful setting for relaxation.
Condo in Wintergreen Resort
4.95 out of 5 average rating, 194 reviews

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.

Guest favourite
A modern living area features a light-colored sectional sofa adorned with a patterned throw. A kitchen with a wood countertop and seating area can be seen in the background, complemented by pendant lighting. Mirrored walls enhance the sense of space, reflecting the inviting atmosphere.
Condo in Mount Jackson
4.87 out of 5 average rating, 110 reviews

Bike,Hike,Relax in Lux! at Bryce Resort

This recently renovated, modern condo offers the latest amenities, including WIFI and Smart TVs. The true charm lies in its outdoor options. Sip a hot drink on the balcony, watch the sunset, or cozy up by the fireplace. In the season, enjoy the Community Pool, explore slopes, lifts, dining, and shops nearby. Golfing, skiing, biking, ziplining, swimming, and canoeing at Lake Laura are a short walk away. Embrace modern comfort and thrilling outdoor adventures!

Top Guest favourite
A cozy living area features two gray sofas positioned around a wooden coffee table. Decorative throw pillows on the sofas offer a hint of warmth. The background reveals an open kitchen with modern fixtures and a light-colored aesthetic, enhancing the space's inviting feel.
Condo in Mount Jackson
4.93 out of 5 average rating, 151 reviews

Ski and Golf Condo Aspen East Condos Unit 212

Newly renovated condo located at Bryce Resort on ski slopes and golf course. This second floor condo faces the golf course with mountain views. Ski in and ski out. Walk to all of Bryce Resort’s amenities including events at the Shenandoah Center. Fully equipped kitchen with Keurig. 2 queen beds and 1 single bed. Wood burning fireplace. Smart TV’s in living room and bedroom. Washer and dryer. Walk-in shower. Wi-fi. Outdoor pool open seasonally.

Top Guest favourite
A light-filled living area features a spacious sectional sofa paired with two side chairs. A wooden coffee table is centrally positioned on a soft area rug. Large sliding doors lead to an exterior space, while a smart TV is mounted against the wall.
Condo in Bridgewater
4.99 out of 5 average rating, 145 reviews

3 BR, 3 bath, BWC, EMU, JMU, 1-81 *WIFI* Buc-ee's

Kitchen * Wi-fi * Free Parking * Air Conditioning. This beautiful townhouse is located in the heart of the Shenandoah Valley in the quaint, small town of Bridgewater, Virginia. It is located very near Bridgewater College and the Bridgewater Retirement Home. It is also within a few minutes of EMU (Eastern Mennonite University), JMU (James Madison University). and Dynamic Aviation and has easy access to I-81.

Guest favourite
A cozy living area features soft sofas arranged around a wooden coffee table. A stone fireplace occupies one wall, with a fire burning brightly. Large windows provide natural light and a view of the surrounding landscape.
Condo in Wintergreen Resort
4.87 out of 5 average rating, 127 reviews

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!

Top Guest favourite
A spacious living area features a wood-burning fireplace surrounded by light-colored walls. A comfortable couch, adorned with a welcoming throw pillow, faces a wooden coffee table. Natural light enters through large windows, offering views of the outdoor greenery.
Condo in Wintergreen Resort
4.93 out of 5 average rating, 253 reviews

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.

Top Guest favourite
A serene outdoor view features rolling hills in the distance under a vibrant sunset sky, blending warm hues of orange and pink. Green grass covers the foreground, accented by a small flower bed with rocks, enhancing the natural beauty of the landscape.
Condo in Wintergreen Resort
4.97 out of 5 average rating, 129 reviews

Panoramic Views | Sunrise on the Deck | Nelson 151

Enjoy peaceful mountain mornings and sweeping Blue Ridge views from this updated 2-bedroom condo at Wintergreen Resort . Sip coffee on the deck at sunrise, relax by the cozy fireplace, and explore nearby hiking, wineries, and the famous Nelson 151 Craft Beverage Trail. Two king bedrooms, two full baths, and a sleeper sofa sleep up to 6.

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