Condo holiday rentals in Shenandoah Valley

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.

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!

Stylish*Updated*Central*Walk to Slopes*Dogs OK!

Step into the allure of our fantastic Wintergreen, just a leisurely 4min stroll away from the heart of Wintergreen's mtn action! Tucked away in a serene and tranquil nook of the mountain, our meticulously curated property combines serene relaxation with unfettered access to the thrilling outdoor adventures that await nearby. The closest hiking trail is within 200 yds! Whether you're a couple seeking a romantic retreat or a small, fun family, our home is eager to embrace your mountain dreams!

Mountain view retreat #1

Get comfortable with mountain views and fresh, clean air at 3,200' altitude, close to Canaan Valley/Blackwater Falls State Parks. Also, Dolly Sods, Seneca Rocks and Spruce Knob (highest point of WV). Lots of hiking/biking trails. Unique shopping in Davis and Thomas with a variety of restaurants. Fast food? An adventurous, scenic drive goes to Parsons, with the only McDonald's and traffic light in the county. Relax on the back deck to view the horse pasture and the small private airport.

2-min drive to slopes, stair-free/free firewood!

Peaceful, recently renovated mountain-top retreat. Relax or work from home. End your day with a hike or spa treatment around the corner—linger with a glass of wine at sunset. It’s all 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 HOA pools CLOSED for season

1 bedroom condo, walk to the slopes !

Cozy 1BR Wintergreen condo ⛷️❄️ 5-minute walk to the ski slopes, resort village, and mountain-too market, with snow tubing only minutes away. Enjoy a fully stocked kitchen, premium coffee and teas, cooking oils and spices. Relax by the wood burning fire 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 close access to the village for après-ski.

BlueRidge Getaway- Dog Friendly

Relax and enjoy spectacular top-floor mountain views from the deck. This recently renovated unit is at the top of the mountain close to many hiking trails. Visit the Wintergreen village, with its restaurants and shops, with a 5 minute drive or an easy hike through the woods. You also have access to Rhodes Farm and Chestnut Hills pool. This condo is convenient to Devils Backbone, Bold Rock, and the litany of other breweries, cideries, distilleries, and restaurants. Dogs welcome!

Third & Thornrose, Staunton Condominium

Our guests stay upstairs in our 1929 American Foursquare house. Central air; separate entrance, wooden floors. Daily, weekly or monthly rates. Small, fully-equipped kitchen with stove and refrigerator, small dining room. The bathroom has a tub and shower. Television with Netflix. Wifi and off-street parking. Two bedrooms (queen-sized bed, two XL twin beds), living room. Short walk to Gypsy Hill Park, 1 mile to historic downtown (Trolley). Small town, Big Magic!

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!

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!

Mountain View Condo at Wintergreen, Wood Fireplace

Breathe in the crisp mountain air, cozy up by the fireplace, and soak in sweeping views of the Blue Ridge Mountains. This clean, comfortable 2-bedroom condo at Wintergreen Resort features two king beds, two full bathrooms, and a sleeper sofa—perfect for up to 6 guests. Enjoy panoramic windows overlooking the mountains,, a fully stocked kitchen, in-unit washer/dryer, central heat/AC, and free parking. The shuttle to the ski lodge is just steps away!

3 BR, 3 bath, BWC, EMU, JMU, 1-81 *WIFI* Buccees

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.