Cabin vacation rentals in Wintergreen Resort

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Top-rated cabin rentals in Wintergreen Resort

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Top guest favorite

The cabin features a screened-in porch that allows for outdoor relaxation while offering shelter from insects. Surrounded by greenery, it sits on a gentle slope with trees and hills visible in the background. A simple pathway leads to the entrance, enhancing accessibility.

Cabin in Roseland

4.96 out of 5 average rating, 720 reviews

Cozy Mountain Cabin

Snuggled in the Blue Ridge. Secluded from the crowds. Experience your visit in an authentic log cabin. Spacious sleeping loft. Perfect romantic escape, friends getaway, or personal retreat. Workout area/sitting room. Fresh eggs (in season), wine, tea, coffee. 1G Internet, SMART TV. A/C. Less than 2 miles to Devil's Backbone and Bold Rock. Minutes from App. Trail, Wintergreen Resort, breweries, wineries, cideries, restaurants, horseback riding, hiking trails, outdoor concerts, & antique shopping.

Top guest favorite

Cabin in Roseland

4.97 out of 5 average rating, 235 reviews

Secluded~Gameroom~Firepit~Ski/Wine Hop~Mtn View!

The Blue Ridge Cabin is at the base of the mountain on the “151 Brewridge Trail”, just mins to wineries, breweries, hiking, skiing, golfing & lake fun. Experience a mountain vaca in this fun bear-themed cabin on 2 private acres, tucked away yet close to it all! Enjoy 12+ wineries & breweries just 15mins away, 1/2 mi to Devils Backbone Brewery, 1 mi to Bold Rock Cider, 10 mins to Appalachian Trail, Shenandoah Nat. Park & Wintergreen Ski Resort! The must see spots are so close, you can see it all!

Top guest favorite

The log cabin stands surrounded by trees, featuring a metal roof and warmly lit exterior. A gas grill is positioned nearby, complemented by four Adirondack chairs set around a small fire pit, offering a cozy outdoor gathering space.

Cabin in Lyndhurst

4.97 out of 5 average rating, 137 reviews

Cozy Log Cabin

Relax and unwind in this secluded, hand-hewn log cabin with all the modern conveniences. 10 minutes off the Blue Ridge Parkway from mile marker 16, minutes from Shenandoah National Park and the Appalachian Trail, close to 4 breweries, 6 wineries, 3 cideries, and Wintergreen Four-Season Resort. Located on over 300 acres of private land with plenty of room to explore and enjoy the wildlife. Come witness the brilliant night sky lying in an open field with no city lights to diminish the experience.

Top guest favorite

A rustic cabin nestled among lush greenery is depicted, featuring a wood-paneled exterior and a metal roof. A picnic table is situated nearby, surrounded by garden paths and natural landscaping, with mountains visible in the background under a blue sky.

Cabin in Schuyler

4.99 out of 5 average rating, 218 reviews

Cozy cabin for 2 w/mountain views & trails

Cozy cabin in the woods with beautiful mountain views from covered back deck! Perfect for nature lovers, couples, singles. Ideal for a peaceful escape or visiting local wine/brew trail. While remote, also a convenient base to visit area attractions, hikes & easy drive to C'ville. Relax on the covered back deck watching the sunset and wildlife. Over 2 miles of wooded trails on property for guest use. 15-20 min walk through woods trails (part of this walk is on a hill) to access Rockfish River.

Guest favorite

The rustic exterior of the cabin features weathered wooden siding and a red metal roof. The front porch is adorned with a rocking chair, inviting relaxation. A circular sign is mounted above the door, adding character to the entrance, framed by greenery.

Cabin in Roseland

4.89 out of 5 average rating, 526 reviews

Catrock Cabin and Open Heart Inn

This cozy and charming cabin was originally built as a country store in 1930 and has been updated with all the modern comforts. NEW in 2025- bathroom fully renovated with walk-in tiled shower! The cabin has a front porch perfect for sunset, back deck with gas grill, full kitchen, king bed, queen sofa bed, mountain views, and ten acres to explore. Come unplug and get away from it all! Tucked away on the “quiet” side of the famous route 151, we are minutes from trails, breweries, and more!

Guest favorite

Cabin in Nellysford

4.96 out of 5 average rating, 228 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.

Guest favorite

Cabin in Wintergreen Resort

4.88 out of 5 average rating, 129 reviews

The Bear Dance Cabin at Wintergreen Resort

Tucked back in the woods in the Wintergreen Resort, we're on the top of Wintergreen Mountain, elevation just under 4k, near all the resort's amenities. Our family built on Wintergreen Mountain after learning how unique and beautiful the seasons are here. The cabin quickly became a new member of the family and we can’t imagine not having her in our lives now. Ten years after building we decided to provide short term rental and the experience has been beyond what we had ever imagined. Enjoy!

Guest favorite

A charming cabin is nestled among bare trees, with snow blanketing the ground. The wooden exterior features a spacious front porch with a railing, illuminated by soft lights. A clear pathway leads to the entrance, enhancing the cabin's cozy, wintery setting.

Cabin in Nellysford

4.93 out of 5 average rating, 138 reviews

Cedar Base Camp

Enjoy everything in the area to enjoy your holiday in this cozy cabin at the top of Wintergreen. You will have plenty of room with three bedrooms and a loft. Meals can be prepared and enjoyed with the well appointed kitchen and propane grill on the deck. Everyone will love the rustic bathroom with tin tub, or the European style rain shower in the master bathroom. Relax after an exciting day in the private hot tub. Hiking is down the street and the resort is just down the mountain.

Guest favorite

Cabin in Afton

4.96 out of 5 average rating, 215 reviews

Inn at the Woods: Updated Cabin w/Mountain Views

Fall in love with the charm of this recently updated ‘Hansel & Gretel’ style cabin located on Castle Rock Mountain. This cabin has 3 bedrooms + a loft, with a total of 4 queen beds. Hike and explore the 20+ acres or relax on the large multi-tiered deck and fire-pit area while soaking in the mountain sunsets. Enjoy nearby dining, breweries, or wineries, the historical town of Charlottesville, or spa, golf, tennis, and skiing at the Wintergreen Resort - both just a short drive away.

Top guest favorite

Cabin in Vesuvius

4.99 out of 5 average rating, 354 reviews

The Sanctuary

Nature lovers paradise! Named "The Sanctuary" for the place you can UNPLUG, unwind & find your peace! Perched up high on nearly 60 acres- you are sure to get fresh air & the rest you are searching for! Only 4 miles to Wintergreen, 6 miles to Sherando lake and backs up to the Blue Ridge Parkway there are plenty of things to do OR just relax and enjoy the crickets & stars! With crazy careers, growing kids & constant hustle- everyone needs a hide out like this every now and then!

Guest favorite

A cozy wooden cabin is nestled among lush greenery, showcasing a well-kept exterior. A covered porch leads to the entrance, surrounded by natural landscaping and stone pathways. Tall trees provide shade, enhancing the serene setting.

Cabin in Faber

4.98 out of 5 average rating, 181 reviews

Adorable Cabin on 33 Private Wooded Acres

Tucked away on 33 wooded acres, Buck Creek Cabin offers a peaceful retreat with forest, meadow, and mountain views. Trails wind past the creek through wildlife-rich terrain. A deck and covered porch invite alfresco meals or quiet evenings under the moon. Minutes from breweries, wineries, and distilleries, and a short drive to the Blue Ridge Parkway, AT trailheads, Wintergreen Resort, or Charlottesville. Lightning-fast internet keeps you connected while you unwind.

Guest favorite

Cabin in Faber

4.96 out of 5 average rating, 134 reviews

Hot Tub@ Lakefront Cabin w Stunning Curated Decor

✨ A Marvelous Night for a Moondance Awaits ✨ Welcome to Moondance—a lakeside log cabin with serious style and mountain soul. Designer interiors, cozy fireplaces, an après-ski game room, and dreamy views set the stage. Whether you're sipping wine on the deck or roasting s’mores under string lights, this is where memories are made. Minutes to wineries, Wintergreen, and the Blue Ridge Parkway. Relax, reconnect, and maybe do nothing at all. We support that.