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, 693 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, 225 reviews

Brewery/Hiking 1mi~Lake 5mi~Pet Friendly~Gameroom!

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, 121 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

4.98 out of 5 average rating, 198 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 cabin is situated on elevated stilts, featuring a light grey exterior and a contrasting red door. A white railing encircles a spacious deck, surrounded by trees with autumn foliage, emphasizing the cabin's peaceful setting in nature.

Cabin in Montebello

4.99 out of 5 average rating, 101 reviews

Scenic cabin with direct hiking to N Forest and AT

Secluded cabin on 11 acres of land adjacent to George Washington National Forest at 3k elevation. Fully furnished two-bedroom, two-bathroom cabin with heat, AC, WiFi, and wood stove. Queen-size bed downstairs / full-size with a trundle upstairs. Extra fee for guests 5 & 6. The third “bedroom” is a detached micro cabin with a bunk bed (heat only). Four miles from the Blue Ridge Parkway. Direct hiking from cabin to AT. Level 2 EV charger (30amp 240V) available upon request for $5 fee per night.

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, 107 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, 122 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!

Guest favorite

An historic log cabin is framed by lush greenery, showcasing its rustic wooden exterior with large windows adorned with shutters. A pathway lined with stones leads to the entrance, while a vibrant garden flourishes in front, enhancing the tranquil mountain setting.

Cabin in Montebello

5 out of 5 average rating, 117 reviews

Pre-Civil War Log Cabin w Sauna, Hot tub & Firepit

3 Sisters Cabin is an historic, pre-Civil War log cabin; one of only a few surviving 2-story log cabins along Virginia's scenic Blue Ridge Parkway. 3 Sisters is the only VA property featured in "The Top 100 Most Beautiful Rustic Vacation Properties in North America". We invite you to relax and recharge in the cabin, sauna and hot tub because you deserve it! Lay in the comfy QUEEN sized bed to stargaze at the beautifully lit sky through the skylight. Two TWIN beds as well. Sleeps 4.

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

4.87 out of 5 average rating, 127 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, 101 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, 202 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.