Holiday rentals in Dripping Rock

3 Levels · 3 Scenic Decks · Game Room · Hot Tub

Wake up to Blue Ridge views and start the day with coffee on the deck. Rockstar Ridge sleeps 12 across 3 levels, with 5 bedrooms, 3.5 baths, and 2 wood-burning fireplaces for cozy evenings. Soak in the private hot tub, fire up the gas grill, and gather in the music-themed game room with a pool table, foosball, arcade, and a Victrola music player. You'll also find a fully stocked kitchen, a wine and coffee bar, a washer and dryer, and a workspace. Wintergreen Resort is just 6 minutes away.

Location · Family · Wifi

NO STEP ENTRY Wintergreen Mtn Home,HotTub,Sleeps10

We had to create a new listing for this property. Previous listing had 70+ reviews with a 4.8 Star rating. Same great host and same great house, just a new listing. Screenshots of old listing in additional photos. Stay at this luxurious 4-bedroom, 3-full bath vacation rental home for 10 in Wintergreen, within minutes of top-notch golf courses, skiing / snow boarding at the Mountain Inn, and dozens of hiking trails . In addition to the unbeatable location, the property offers a private hot tub!

Value · Family · Pets

Best Blue Ridge Views at Sunrise over Wintergreen

Spectacular Mountain Views & Sunrises Spend your days hiking over 30+ miles of trails (including the Appalachian Trail), driving the Blue Ridge Parkway, kayaking the lake in the summer, leaf peeping in the Fall, skiing one of the regions best mountains in the winter, or exploring Virginia's brewery and wine country. Whichever you choose, we're positive you'll enjoy your time at Sunrise over Wintergreen! New host family of beloved 250+ ★★★★★ 'Best View in the Blue Ridge from Biscuit's Porch'.

Location · Value · Check-in

Mountain Overlook House - Blue Ridge Parkway

Unique octagonal house with stunning views of the Blue Ridge Mountains of Virginia. Located 2 miles from I-64, 15 minutes to downtown Waynesboro and an easy 25 min drive to Charlottesville and UVA. Open floor plan, perfect for gathering, and long-range 180 degree views from nearly every room. Fully equipped renovated kitchen. Quality linens and bedding. Rustic, yet modern decor. Home features large fireplace, outside fire pit, wifi, and board games galore. Stargazing and birdwatching heaven.

Family · Location · Indoor spaces

Laurel Springs Retreat

Cozy year round mountain retreat in Wintergreen Resort - whether it's Fall leaf peeping; Skiing at Wintergreen Resort; Spring wildflowers; or Summer cool temperatures. Perfect for hikers, skiers, nature lovers, and families looking to relax in a peaceful setting. Quiet forested cabin close to the Appalachian Trail, 30+ miles of Wintergreen Nature trails including Shamokin Springs waterfalls; Devils Knob Golf, cycling on the Blue Ridge Parkway, and Wintergreen for skiing and year-round fun.

Location · Value · TV

Afton, Mountain View Mini Farm

Welcome to Mountain View Mini Farm! We are located in the Rockfish Valley(Afton, VA)with amazing views of the Blue Ridge Mountains. Our farm is just minutes to wineries, breweries, cideries, Shenandoah National Park and more! There is so much to do close by, but once you get on the farm, you won't want to leave! We have a total of 5 horses, with 3 being mini rescue horses. There's a fire pit area where you can roast S'mores while you watch the sunset. Be sure to look at bedrm 2 description.

Location · Family · Cleanliness

Blue Ridge Mt retreat steps off Appalachian Trail

Escape to this stunning 3-story Wintergreen mountain retreat, steps from the Blue Ridge Parkway and Appalachian Trail. Featuring a lighted circular driveway and three private porches, it offers ample space for relaxation. The top floor includes two bedrooms and a large bath. The main level boasts a den, kitchen, master bedroom, and a fully stocked kitchen with a 10-seat dining table. The bottom floor features another master bedroom and a bunk room. Unwind by the cozy fireplace or hot tub!

Value · Location · Cleanliness

Serene Wintergreen Retreat, Nestled in the Trees

Welcome to our cozy Wintergreen cabin in the trees! You'll truly feel at peace with nature on the three levels of decks and great privacy. The interior has been fully renovated with modern finishes. The light-drenched living room with a wall of windows brings the sense of nature inside. Outside, enjoy the hot tub, covered dining for 10, firepit, and grill/pizza oven area. We are close to skiing and some of the best hiking trails, wineries, and breweries in Virginia. Plus, pet friendly!

Value · Family · Laundry

Cliffs Edge - It’s Pumpkin Spice Time!

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.

Family · Location · Condition

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.

Location · Family · Decor

Newly Built Designer Home in Wintergreen

Welcome to Onyx Hill, a custom built 4-bedroom, 3.5-bathroom home nestled within the picturesque Wintergreen Resort! Every inch of this home has been designed with impeccable attention to detail and designer finishes, ensuring a memorable stay. *Newly built in 2023 *Fully equipped gourmet kitchen *Family room w/ electric fireplace, 65” TV *FAST WiFi *Smart TV in every bedroom *Pet friendly! (1 dog max) Managed by Chris at New School Hosting. Click my profile for more reviews.

Family · Value · View

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!

Family · Location · TV