Holiday houses in Wintergreen Resort

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Top-rated holiday rentals in Wintergreen Resort

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Guest favourite

Condo in Wintergreen Resort

4.91 out of 5 average rating, 100 reviews

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.

12 – 19 May

$1,792 AUD total

Guest favourite

Condo in Wintergreen Resort

4.96 out of 5 average rating, 233 reviews

Five Minute Walk to Everything!

**Pet friendly** two bedroom, two bath, loft style condo centrally located at Wintergreen Resort. Ski check-in, 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 master 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.

25 Aug – 1 Sept

$1,738 AUD total

Guest favourite

Condo in Wintergreen Resort

5.0 out of 5 average rating, 165 reviews

Wintergreen: Mountain View for Miles Sunset Vista

Welcome to Sunset Vista Villa! This beautifully appointed, 2 bedroom, 2 bath, first-floor-unit with second story views, is centrally located to all of the amenities the Wintergreen Resort has to offer. It comfortably sleeps five and with its western vistas, sunsets are a thing to behold! Whether you spend your days hiking, skiing or enjoying the wineries and breweries, Sunset Vista Villa will be sure to enhance your stay. Book today & come enjoy the Wintergreen Resort and Blue Ridge Mountains!

24 Sept – 1 Oct

$2,370 AUD total

Guest favourite

Condo in Wintergreen Resort

4.91 out of 5 average rating, 177 reviews

A True Mountain Getaway! Ski in/Ski out!

Located steps away from the top of the ski slopes at Wintergreen Resort. No snow? No problem! Enjoy the cool mountain breezes, hiking and climbing trails, mountain lakes with beaches, wineries, breweries and much much more. Restaurants and shopping within walking distance. Our place has a galley kitchen and small refrigerator, a large deck to enjoy a quiet dinner and has been newly decorated. There is a king sized bed and a smaller fold out sofa that could accommodate two small children.

25 Aug – 1 Sept

$1,263 AUD total

Guest favourite

Condo in Wintergreen Resort

4.99 out of 5 average rating, 116 reviews

Amazing Blue Ridge ski-front views with Wintermint

Experience one of the best year-round locations at Wintergreen in this 1 bedroom/1 bath, slope-front 1.5 level condo in the heart of the Wintergreen Resort! This incredible spot offers a quiet and cozy getaway for 2 guests seeking adventure or nothing at all. Enjoy the ability to ski-in/out from the property during the wintertime and explore the hiking trails during the summer. It's a short walk to the Mountain Inn (next door), 3 restaurants/bars, shopping, Starbucks, and outdoor activities.

30 Apr – 7 May

$1,514 AUD total

Guest favourite

Condo in Wintergreen Resort

4.95 out of 5 average rating, 197 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.

6 – 13 Sept

$1,394 AUD total

Guest favourite

Cabin in Roseland

4.96 out of 5 average rating, 651 reviews

Cozy Mountain Cabin

Snuggled in the Blue Ridge. Secluded from the crowds. Experience your visit in an authentic log cabin. Perfect romantic getaway or personal retreat. Less than 2 miles to Devil's Backbone and Bold Rock. Minutes from the Appalachian Trail, Wintergreen 4-Season Resort, many breweries, wineries, cideries, restaurants, horseback riding, hiking trails, outdoor concerts, and antique shopping. Complimentary hot cocoa, tea, coffee, popcorn. High-speed internet, SMART TV. Air Conditioning.

31 Dec – 7 Jan

$1,510 AUD total

Guest favourite

Condo in Wintergreen Resort

4.96 out of 5 average rating, 105 reviews

All-Season 2bd/2ba next to Spa view of Golf Course

Come experience four seasons of fun- hit the ski slopes, hike the blue ridge mountains, enjoy local cider or beer, or cozy up by the fire and enjoy the mountain views. Located across the street from the aquatic/fitness center & spa, on the Devil's Knob golf course, and next to the ski shuttle pickup location and Nature Foundation, the location couldn't be better. The unit has a spectacular sunset view from the balcony, a gas fireplace, and speedy wifi for working or streaming!

22 – 29 Jan

$1,990 AUD total

Guest favourite

Condo in Wintergreen Resort

4.99 out of 5 average rating, 175 reviews

Cozy getaway w/ heated floors, dog friendly

Close your eyes and imagine opening the door to a beautifully handcrafted live edge oak breakfast bar with 4 leather bar stools, granite countertops and stainless steel appliances. As you walk into the living room, two plush, comfy leather sofas beckon you to rest & relax in front of the fireplace. Sleeps 3. Comfy wrought iron QUEEN bed for a good night’s rest and a twin pull out in the living room. There is radiant heat flooring throughout our home to pamper your feet.

7 – 14 Sept

$1,706 AUD total

Guest favourite

Condo in Roseland

4.94 out of 5 average rating, 202 reviews

Mountain Getaway - Unbeatable Views

One bedroom, one bath mountaintop condo featuring wood-burning fireplace, wrap-around deck, and amazing views. Located on the first floor with parking directly outside. Bedroom features a queen bed and TV. Only 1.5 miles to Mountain Inn and ski slopes. Unit is located in the High Ridge Place complex along Blue Ridge Drive at the Wintergreen Resort, although the address is Roseland, VA. A resort map can be found on the Wintergreen website. Address will be sent upon booking.

16 – 23 June

$1,794 AUD total

Guest favourite

Apartment in Rockfish

4.99 out of 5 average rating, 157 reviews

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 – 12 Nov

$2,152 AUD total

Guest favourite

Condo in Wintergreen Resort

4.98 out of 5 average rating, 171 reviews

Best View in the Blue Ridge from Biscuit's Porch

One of the best sunrise views in the Blue Ridge Mountains! Spend your days hiking over 30+ miles of trails (including the Appalachian Trail), driving the Blue Ridge Parkway, kayaking in the lake in the summer, skiing one of the regions best mountains in the winter, or exploring Virginia's brewery and wine country. Whichever you chose, we're certain you'll enjoy your time at Biscuit's Porch. We're excited to help you have the best Blue Ridge Getaway!

7 – 14 May

$2,406 AUD total