Vacation rentals in Wintergreen

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Top-rated vacation rentals in Wintergreen

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Guest favourite

Condo in Wintergreen Resort

4.96 out of 5 average rating, 236 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.

Nov. 18 – 25

$259 CAD per night

Guest favourite

Condo in Wintergreen Resort

5.0 out of 5 average rating, 166 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!

Sep. 15 – 22

$306 CAD per night

Guest favourite

Condo in Wintergreen Resort

4.91 out of 5 average rating, 179 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.

Oct. 14 – 21

$184 CAD per night

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.

May 29 – Jun. 5

$183 CAD per night

Guest favourite

Cottage in Tyro

5.0 out of 5 average rating, 186 reviews

Bear Creek Inn

You will be renting the 2 bedroom cottage, optional 3rd bedroom, very large, fenced yard for your pet. Relax at this quiet, peaceful place with year round trout stream. Minutes from the breweries and wineries on Nelson 151. Plenty of outdoor activities to enjoy. The George Washington National Forest is across the street for exploring, hiking and hunting. The house is only 4 miles from Crabtree Falls and several minutes from the Appalachian Trail access. Wintergreen Resort is 12 miles away.

Sep. 3 – 10

$250 CAD per night

Guest favourite

Cabin in Nellysford

4.98 out of 5 average rating, 162 reviews

Tiny Luxury Retreat: Lake, Hikes, Brews & Vines

Welcome to our luxurious tiny house nestled in the heart of Nelson County, Virginia. This enchanting retreat, surrounded by the majestic Blue Ridge Mountains, offers an unparalleled experience in a landscape dotted with wineries, breweries, distilleries, and sprawling farmland. This luxury tiny house was built in 2022 and is available for couples, solo travelers, or a small family wanting to explore this beautiful stretch of the Blue Ridge Mountains. FREE Electric Vehicle Charger on-site.

Feb. 26 – Mar. 5

$236 CAD per night

Guest favourite

Cottage in Roseland

5.0 out of 5 average rating, 178 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!)!

Sep. 15 – 22

$222 CAD per night

Guest favourite

Condo in Wintergreen Resort

4.95 out of 5 average rating, 201 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. 10 – 17

$176 CAD per night

Guest favourite

Cabin in Roseland

4.96 out of 5 average rating, 653 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.

Jul. 30 – Aug. 6

$191 CAD per night

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.

Aug. 8 – 15

$216 CAD per night

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.

Jun. 17 – 24

$227 CAD per night

Guest favourite

Cabin in Vesuvius

4.97 out of 5 average rating, 161 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.

Sep. 27 – Oct. 4

$200 CAD per night