Holiday rentals in Dripping Rock

Ultimate cabin in the mountains

This unique and secluded cabin sits on 75 acres in the Blue Ridge mountains. Enjoy the cozy wood fireplace, hot tub, charcoal grill, and fast, reliable fiberoptic internet if you need to get some work done while you're away. It has a washer and dryer, a full kitchen, and is pet-friendly (no pet fee!), so you can enjoy it with the whole family. There is a 4K 55” smart TV with apps, a Tesla LVL 2 charger, a cabinet full of board games, books, and plenty of items to entertain both kids and adults!

Cozy Mountain Cottage on Brew/Wine Trail-King Bed

Welcome to the Sugah Shack, a cozy, beautifully appointed new construction cottage nestled in the foothills of the Blue Ridge Mountains! Located midway on the Brew Ridge Trail, but 500 yards off the byway, so guests have a quiet retreat. Perfect for romantic getaways, destination telework space, or families exploring this outdoor paradise community. Stunning property boasts beautiful vistas with sweeping 300-degree mountain and a year-round calendar of outdoor activities. GAS FIREPLACE/FIREPIT

Romantic Yurt~On 151 Brew Trl~Nat. Park & DB 5 min

Come for a memorable stay at the Rockfish Valley Yurt and enjoy "glamping" at its finest! Picturesque mountain views await at this magical yurt conveniently located ON the “151 Brew Ridge Trail", on 3 acres close to popular attractions- Nat. Park & hiking 2 mi, Lake 10 mi, Devils Backbone Brewery 1 mi, Bold Rock 2 mi & Wintergreen Spa/Ski/Tube 10 mi. You’ll have 15+ wineries & breweries within a 20 min radius. It’s a one of a kind experience here! Create memories that will last a lifetime!

Historic cottage with stunning mountain views

Welcome to Rose Cottage in picturesque Albemarle County, where you'll enjoy expansive 360-degree views of the mountains surrounding historic Cove Lawn Farm. Relax in the tranquil rural setting or stroll more than two miles of comfortable walking paths that wind through 25 acres of stream-lined hayfields. From Rose Cottage, you're just minutes from the best local cideries, distilleries, and wineries including Pippin Hill Farm & Vineyards. Easy 20-minute drive to UVa and 22 minutes to Monticello.

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.

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.

Ski season is coming! Time to book your trip! SNOW

Wintergreen mountain house located yards from the Blue Ridge Parkway & Appalachian Trail! The house is 3 stories with several porches, 3 of them are private. It has a lighted circular driveway. The top floor has two bedrooms & one large bathroom. The main living area is on the second floor with a master bedroom. The bottom floor has another master bedroom, & additional bunk room. The kitchen has a 10-seat kitchen table. After a long day enjoying the outdoors, relax by the fireplace or hot-tub!

Luxury Condo in the Sky! Finest in Wintergreen!

Welcome to our recently renovated luxury condo in the sky! Perched on the edge of the Wintergreen ridgeline, we are just a stone’s throw from nature’s bounty. Our condo offers the perfect blend of relaxation and access to recreation. Hit the ski slopes, take a hike, or explore the bountiful brew and wine scene and then come enjoy the view. The horizon is 75 miles distant from our balcony on a clear day! We love hosting families with kids or couples coming to enjoy all that Wintergreen offers!

Luxe Yurt w/Hot Tub in the Heart of the Blue Ridge

Experience glamping, Blue Ridge style. Our luxury yurt is located at the top of a small hill, in the center of a 70 acre farmstead surrounded by natural beauty. Night Archer Farm is located off a quiet country road in Afton, Nelson County. It is private, but not remote. You are close to the Brew Ridge trail, wineries, breweries, skiing at Wintergreen, Blue Mountain Brewery, Devil's Backbone, golf, hiking, or driving the Blue Ridge Parkway. Hike directly from the Yurt up into the mountains!

1 bedroom condo, walk to the slopes !

Cozy 1BR Wintergreen condo ⛷️❄️ 5-minute walk to the ski slopes, resort village, and mountain-too market, with snow tubing only minutes away. Enjoy a fully stocked kitchen, premium coffee and teas, cooking oils and spices. Relax by the wood burning fire and enjoy a smart TV, fast WiFi and games. Comfortable queen bed in the bedroom plus new queen sleeper sofa in the living room. Private furnished patio with peaceful wooded views and close access to the village for après-ski.

Blue Ridge Bliss - For family & friends to enjoy!

Welcome to Blue Ridge Bliss! Come enjoy the mesmerizing mountain top views of this well-appointed condo in The Ledges of Wintergreen Resort. It’s the perfect place to unwind, unplug and recharge. Whether here to ski, hike, or visit Virginia wineries, cideries, or craft breweries you’re sure to enjoy the beautiful views from the living room and deck. A short walk to The Highlands lift and across the street from Fire & Frost eatery and the Wintergreen Spa, this is an ideal location.

Cliffs Edge -A Contemporary Mountain Home

An open floor plan with high ceilings and large skylights, this amazingly engineered home will stun you with its incredible mountain views! This spacious home, with its cantilevered decks, makes this perfect for any family. The large upstairs loft, adjacent to the upstairs bedrooms, offers movies, games, puzzles, and comfortable seating. Wi-Fi, Netflix, and Samsung Smart hub give plenty of entertainment options. The spacious living area and dining room have abundant seating for all.