
Cabin vacation rentals in Wintergreen Resort
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Top-rated cabin rentals in Wintergreen Resort
Guests agree: these cabins are highly rated for location, cleanliness, and more.

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.

Near Ski/Tubing, Wine/Breweries-Gameroom-Fireplace
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!

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.

Wintergreen Retreat! Hot tub, 2 Fireplaces, Views
The Rockstar Ridge is a spacious 3300 sq ft retreat in the serene & scenic Wintergreen Resort area - just a 6 minute drive to the slopes. This inviting cabin has 5 bedrooms, 3.5 baths, & sleeps 12. Amenities include 2 wood-burning fireplaces, hot tub, gazebo, pool table, foosball, arcade game, gas grill, Victrola with albums, CDs, cassettes, washer & dryer, plus 3 decks with Polywood furniture & stunning mountain views. Relax & unwind as you enjoy the peaceful surroundings & mountain air.

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.

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!

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.

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.

Stylish 7BR/16 pp Wintergreen Resort Home Ski/Hike
7BR/ 6.5B perfect mountain getaway! Tucked away in the woods & situated on 1/2 acre lot, this peaceful escape is less than 5 min from skiing, hiking, spa, pool, tennis & activity center w/i Wintergreen Resort. This spacious home feat. new ss appl, new furniture, HW flrs, granite cntrs, deck w/new grill, open flr plan, 75” tv, new outdoor furniture, new washer/dryer, darts, games/puzzles & new ping pong table. 6 BRs have en-suite baths & 4 have tvs; very private for large grps.

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.

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!

Modern Mountain Escape-2 King bed, Zero step entry
Escape to this bright, spacious mountain retreat with an open-concept layout and plenty of natural light. Walkable to the trails and 5 minutes to the slopes. Enjoy a fully stocked kitchen, cozy fireplace, and screened porch for relaxing after a day of skiing, hiking, or wine tasting. With 2 King bed ensuites, a queen bedroom, and a fun bunk room, there’s space for everyone to unwind. Thoughtfully designed for comfort, it’s the perfect home base for your getaway.
Popular amenities for Wintergreen Resort cabin rentals
Cabin rentals with a hot tub

Cabin House Retreat/ Nature Getaway with Hot-tub

Roudy’s Retreat: Secluded Mtn Cabin -Hot Tub -Pond

Historic Cabin Hot Tub 3 min toSki Mntn View DogOK

Quiet w/Hot Tub and 6 wineries within 10 mins.

Storybook Cabin (Pet Friendly)

Cabin By The Falls

Three Ridges Cabin-kitchen, fireplace, jetted tub

Modern Nellysford Getaway w/ View: Deck & Fire Pit
Pet-friendly cabin rentals

Country Roads Take Me Home.

Log Cabin w/ Views! 8+ Acres! Pets!

4 BR cabin mins to trails & breweries pets welcome

On The Rocks

140 Acres River trails, Private! Ski Wintergreen!

The Bear Dance Cabin at Wintergreen Resort

Secluded Log Cabin | Mtn Views | Pet-Friendly

Cheerful 3-Bedroom Cabin
Private cabin rentals

Parr's Camp - Nothin' Fancy Fish Camp

Fun Family Adventure: Cozy Retreat Awaits

Bide-a-Wee- Hike the Trails! Close to the slopes!

Rustic Cabin @Wintergreen Resort

Lux Log Cabin Getaway: Wintergreen Shenandoah Val

Majestic Mtn Cabin +5 min to ski&porch sunset view

Haycorn Hollow-Secluded Cabin near wine & brews

The Stilt House at Perkins Hollow
When is the best time to visit Wintergreen Resort?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ812 | ﺩ.ﺇ801 | ﺩ.ﺇ698 | ﺩ.ﺇ646 | ﺩ.ﺇ749 | ﺩ.ﺇ643 | ﺩ.ﺇ676 | ﺩ.ﺇ687 | ﺩ.ﺇ672 | ﺩ.ﺇ775 | ﺩ.ﺇ753 | ﺩ.ﺇ779 |
| Avg. temp | 2°C | 4°C | 8°C | 14°C | 18°C | 22°C | 24°C | 23°C | 20°C | 14°C | 9°C | 4°C |
Quick stats about cabin rentals in Wintergreen Resort

Total vacation rentals
Explore 50 vacation rentals in Wintergreen Resort

Nightly prices starting at
Wintergreen Resort vacation rentals start at ﺩ.ﺇ367 per night before taxes and fees

Verified guest reviews
Over 2,750 verified reviews to help you choose

Family-friendly vacation rentals
50 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Vacation rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
50 of Wintergreen Resort vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Wintergreen Resort rentals

4.9 Average rating
Wintergreen Resort stays are highly rated by guests—averaging 4.9 out of 5!
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- Early Mountain Winery
- Boonsboro Country Club
- The Plunge Snow Tubing Park
- Amazement Square
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- Chisholm Vineyards at Adventure Farm
- Liberty Mountain Snowflex Centre
- Frontier Culture Museum
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