Wintergreen Resort vacation rentals

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Top-rated vacation rentals in Wintergreen Resort

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Guest favorite

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.

May 12 – 19

G$27,804 GYD per night

Guest favorite

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!

Jul 25 – Aug 1

G$37,421 GYD per night

Guest favorite

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.

Aug 25 – Sep 1

G$19,528 GYD per night

Guest favorite

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.

May 25 – Jun 1

G$22,925 GYD per night

Guest favorite

Cottage in Roseland

5.0 out of 5 average rating, 177 reviews

Blue Ridge Cottage - 3 Miles to Wintergreen

Our little piece of Blue Ridge Heaven is ready to share! Cozy - 2 bedrooms (one king, one queen), 1 bath, 956 square feet - well appointed in a terrific location! Beautiful mountain view from the 360 square foot, partially covered deck; fiber optic TV and wi-fi; South Fork of the Rockfish River out back. 3 miles from Wintergreen Resort, 1 mile from Devil's Backbone; Close to great hiking/biking, and many wineries, breweries, cideries, and distilleries (if you're into that kind of thing!)!

Oct 23 – 30

G$28,179 GYD per night

Guest favorite

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.

Aug 7 – 14

G$21,802 GYD per night

Guest favorite

Cabin in Roseland

4.96 out of 5 average rating, 652 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.

Oct 22 – 29

G$25,445 GYD per night

Guest favorite

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.

Jun 2 – 9

G$23,986 GYD per night

Guest favorite

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.

Jun 16 – 23

G$28,436 GYD per night

Guest favorite

Cabin in Vesuvius

4.97 out of 5 average rating, 158 reviews

Whimsical Creekside Cabin

Escape to our cabin in the Blue Ridge Mountains! Fall asleep to sounds of Little Mary’s Creek, enjoy your coffee on the wrap around deck, or delight in exploring your own 7 acres in the forest. Our cabin is a cheerful, clean cottage to come home to- or decide to spend your days on property splashing in the creek and sitting out by the fire pit. We invite you to embrace our simpler way of life where we wholeheartedly believe that life is to be enjoyed and not endured.

Oct 6 – 13

G$24,880 GYD per night

Guest favorite

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.

Nov 5 – 12

G$33,752 GYD per night

Guest favorite

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!

Jun 19 – 26

G$39,402 GYD per night