Holiday rentals in Wintergreen

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Top-rated holiday rentals in Wintergreen

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Guest favourite

Apartment in Wintergreen Resort

4.9 out of 5 average rating, 101 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.

14–21 Jun

€ 154 per night

Guest favourite

Apartment 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!

8–15 Oct

€ 203 per night

Guest favourite

Apartment 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.

2–9 Jan

€ 127 per night

Guest favourite

Apartment 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.

24–31 May

€ 126 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.

15–22 Sep

€ 150 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.

1–8 Dec

€ 170 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!)!

16–23 Jan

€ 151 per night

Guest favourite

Apartment 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.

2–9 Aug

€ 120 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.

23 Feb – 2 Mar

€ 130 per night

Guest favourite

Cottage in Afton

4.9 out of 5 average rating, 483 reviews

Couples Getaway,heart of RT 151,stunning views

The Cottage is conveniently located along the Brew Ridge Trail. Sit on your patio and watch the sun set over Humpback rock and the Blue Ridge Mountains. Amazing location that’s set right in the middle of all the breweries. Spacious 6 acre farm with Route 151 road frontage. This handsome cottage is the perfect romantic get-a-way. Enjoy WiFi, air con, parking, self check-in and all the amenities you need to feel at home. Picturesque mountain views and beautifully landscaped grounds.

13–20 Feb

€ 127 per night

Guest favourite

Apartment 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 Aug

€ 147 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.

27 Sep – 4 Oct

€ 136 per night