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 gravel pathway leads to a charming log cabin, framed by tall trees and surrounded by greenery. A sign reading 'COZY MOUNTAIN CABIN' is positioned near the path, inviting visitors to explore this secluded retreat in the Blue Ridge.

Cabin in Roseland

4.96 out of 5 average rating, 695 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.

Guest favorite

Cabin in Roseland

4.96 out of 5 average rating, 227 reviews

Private Cabin~Gameroom~Fire Pit~Wine Hop/Swim/Hike

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 the App Trail, Shenandoah Nat. Park & Wintergreen Ski Resort! The must see spots are so close that you can see it all!

Guest favorite

A hand-hewn log cabin is situated among a lush wooded area, with a gravel driveway leading to its entrance. A sign displaying 'Cozy Log Cabin' is positioned at the start of the path. Stacked firewood is visible nearby, complementing the natural surroundings.

Cabin in Lyndhurst

4.97 out of 5 average rating, 123 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.

Guest favorite

A rustic cabin exterior is framed by lush greenery, with a wooden deck leading to an inviting front door. A sloped green roof complements the warm wood tones of the cabin, creating a harmonious connection to the natural surroundings.

Cabin in Faber

4.94 out of 5 average rating, 109 reviews

Modern Cabin; River! 13 acres! Hiking! Wineries!

Beautiful cabin -13 acre wooded hillside along Rockfish River. Home provides a wonderful blend of modern comfort (high speed internet, updated kitchen) in a rustic exposed post and beam cabin; 3 floors of living spaces allow options for gathering, working, playing together but also apart. Sliding glass doors lead to a large wrap around porch with gas grill, dining table, plenty of seating and a tree level view of the natural setting and wildlife. So much to explore on the property and nearby!

Top guest favorite

Cabin in Schuyler

4.99 out of 5 average rating, 200 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

A cabin is set amidst colorful autumn foliage, showcasing a covered front porch with red rocking chairs. Steps lead up to the entryway, and the surrounding landscape features fallen leaves and natural terrain, presenting a serene and rustic charm.

Cabin in Wintergreen Resort

4.95 out of 5 average rating, 108 reviews

Hot Tub DogsOK Grill Fireplace Pac Man Pool Tennis

Activities are endless: apple picking, breweries/wineries, hiking, lake, horseback riding, golf, tennis, skiing... Take a peaceful morning walk on path across the street from the cabin. One mile to Founder's Overlook and amazing sunrises! 3min drive to ski, walk to trails. ★Comfortably sleeps 7: Q, Q, Q, single sofa ★Great Room with gas fireplace ★Hot Tub ★FAST Wi-Fi ★Smart TVs ★Ms. PAC-MAN arcade ★Deck ★Grill ★Pack 'n Play ★Highchair Happy dog fee $150. Outdoor pool/tennis access included.

Top guest favorite

A welcoming log cabin exterior features a spacious front porch with two comfortable chairs and a small table. The porch is framed by sturdy wooden beams, and neatly stacked firewood is visible on the side. Lush green grass surrounds the cabin, enhancing the natural setting.

Cabin in Schuyler

4.99 out of 5 average rating, 123 reviews

Very Private Cabin - H'Owl at the Moon Farm

"Into the forest I go... to lose my mind and find my soul." -John Muir Incredible cabin nestled in the center of 70 very private acres. Relax and unwind to the sights and sounds of frogs, crickets, & owls. Ideal for families and couples. The Cabin offers close proximity to the James River & tubing, UVA, and many wineries. You will see millions of stars and gain the serenity that can only come from nature. The Cabin is also only 20 minutes away from all that Charlottesville has to offer!

Superhost

A rustic cabin constructed of timber sits amidst a wooded area, showcasing a wraparound porch with steps leading up. Large windows provide glimpses of the surrounding trees, while gravel paths lead to the entrance, enhancing the natural setting.

Cabin in Crozet

4.86 out of 5 average rating, 101 reviews

#4 Cabin Near Wineries, Breweries, UVA, & Hiking

The #4 Loblolly Cottage is an eco-friendly cabin overlooking a lake. Small 450 sq ft, cottage has a queen size bed in the primary bedroom, bunk beds in the second bedroom and a full size futon in living room. Kitchenette equipped with modern appliances and breakfast table. Bathroom and shower. Wi-Fi. Private porch. Pets are welcome for an additional fee. Hike, canoe, fish and bike onsite on a 129 acres. Close by wineries, 15 min to Shenandoah National Park. This cabin is ideal for families!

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, 496 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

The cabin features a warm wooden exterior with a red metal roof, set against a backdrop of lush greenery. A spacious front porch is presented, supported by wooden columns and adorned by wooden railing, inviting guests to enjoy the surrounding nature.

Cabin in Wintergreen Resort

4.88 out of 5 average rating, 128 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!

Top guest favorite

A cozy cabin is nestled among trees, featuring a metal roof and a spacious front porch with black rocking chairs. The gravel driveway leads to the entrance, surrounded by neatly trimmed bushes and a lush landscape.

Cabin in Lovingston

5 out of 5 average rating, 102 reviews

Cabin Overlooking Vineyards of Lovingston Winery

Step off your spacious front porch to stroll through the vineyards of Lovingston Winery! Bring your friends and spend the weekend in a cozy cabin with modern amenities in the famous Monticello wine region. This 64 acre property includes pre-civil war oak trees, mountain views, and a pond with otters! We encourage you to explore the property and enjoy a glass of Lovingston Wine. There's a chance you could be greeted by a mini horse or two! Sleeps 6 comfortably, cot for 7, extra charge.

Guest favorite

A two-story cabin features a light-colored exterior with a steep roof and large windows. A wraparound deck includes wooden railings draped with soft outdoor lighting. A walkway leads from the deck to the landscaped area, surrounded by lush greenery.

Cabin in Afton

4.97 out of 5 average rating, 204 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.