Holiday rentals in Dripping Rock

4.96 out of 5 average rating, 700 reviews

Cabin in Roseland

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.

4.92 out of 5 average rating, 580 reviews

Guest house in Afton

Spacious Tiny Home Close to Wine, Beer & Mountains

A six-figure tiny home in the epicenter of VA's Brew Ridge Trail. FORBES listed this model as the most beautiful tiny house in the world. "Big Tiny", built in 2017, is a luxurious retreat that is huge on both character and amenities. This handcrafted home boasts a full-sized kitchen private bedroom, cozy sleeping loft, 2 large screen TVs, and full bath with tub. With a cathedral ceiling and walls of windows, this Escape Traveler XL is the flagship offering of the premiere tiny home builder.

4.97 out of 5 average rating, 125 reviews

Cabin in Lyndhurst

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.

4.97 out of 5 average rating, 147 reviews

Home in Nellysford

Glass House | Mountain & Water Views @ Wintergreen

This custom home at the base of Wintergreen is located 40-minutes from Charlottesville. The waterside setting offers views from living, primary bedrooms, decks and porches, as well as upstairs bedroom and balcony. Large glass walls and sliding doors ensure connection with the landscape. A two-person master-bathroom shower with views of the pond is a key feature of the home's sleek and minimalist design. The home is off of the Rte. 151 beer/wine/distillery trail and nestled beside a golf course.

Superhost

Home in Roseland

4.88 out of 5 average rating, 143 reviews

Summer is in the air! Time to enjoy natures best!

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!

4.97 out of 5 average rating, 119 reviews

2 bdrm/2 full bath Best Views of Blue Ridge Mtns.

Best View of the Blue Ridge Mountains! Panoramic window views from the great room, dining area and kitchen. If you want to get a closer look step out on the observation deck to see the beautiful mountains and ski slopes (seasonal). Patio furniture is on the deck to enjoy morning sunrises and evening sunsets. All new stainless steel appliances in kitchen, Freshly painted throughout. 2 bedroom 2 bath Lots of activities to do at the Wintergreen Resort all year long. Year round resort activities.

4.99 out of 5 average rating, 234 reviews

Cottage in Afton

Oasis in the Blue Ridge -Rt. 151 Brew Ridge Trail

Welcome to the Glass Hollow Cottage! Come make yourself at home and enjoy the rustic charm of our custom hand-built cottage. A perfect getaway for a couple or friends who want a 1-of a-kind destination. Adventure and R & R await you!!! Enjoy the well stocked kitchen & the bright, clean, cheery ambience.... everything you need to feel at home & then some. Prime location: Just minutes to Rt. 151/Brew Ridge Trail, dozens of popular wineries/breweries, Wintergreen Resort & Shenandoah Nat. Park.

5 out of 5 average rating, 914 reviews

Yurt in Afton

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!

4.99 out of 5 average rating, 274 reviews

Farm stay in Afton

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.

Guest suite in Waynesboro

4.98 out of 5 average rating, 294 reviews

The LoriAnn, A Boutique Stay New Sleep Number Bed

This beautifully restored 1940’s home is located in the City of Waynesboro just a short drive from the Blue Ridge Parkway. Modern amenities, complimentary breakfast items and assurance of comfort awaits! Enjoy one of a kind Autographed Movie and TV Memorabilia. The spacious front porch is all yours including a 100 yr old porch swing that belonged to my Great Grandmother. Along with the Parkway & Skyline Drive, enjoy Restaurants, Breweries, Vineyards, movie theaters and exploring Route 151.

Home in Wintergreen Resort

4.96 out of 5 average rating, 105 reviews

Cliffs Edge- Hike, Play & Splash into Summer!

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.

4.94 out of 5 average rating, 250 reviews

Cozy, clean, quiet mountain condo- King bed

Everything you need to make your getaway relaxing and convenient has been thought out in this tastefully decorated condo including new King Bed, Queen sofa pullout bed, plush linens, new spacious couch, 55" & 28" Smart TVs, Roku, WiFi, DVD player & movies, fully equipped kitchen, dining area for 4, wood burning fireplace, and private patio. Non-smoking condo. Please provide all guest names and dog info if applicable upon inquiry or booking. No cats or other animals accepted.

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Other great holiday rentals in Dripping Rock

5 out of 5 average rating, 15 reviews

Home in Crozet

Orso Blu one-of-a-kind VIEWS in Crozet

JamesRating, 5 stars1 week ago

The house is in a beautiful setting surrounded by mountains with peaceful views from the front porch that include a field of lavender and a stream. A forested trail network can be accessed at the far end of the lavender field--so bring your hiking shoes. The house is stunning with clean lines, "european" design and decor that includes high-end appliances and fixtures. Francesca is the ultimate host-very friendly and helpful. She provided all the information and details on the house that you would need for an easy check-in, stay, and check-out. From my initial conversations with her when I booked the house to helpful messages just before and during our stay, I felt like I was staying at the house of an old friend. We look forward to staying at Orso Blu on a future trip!

4.99 out of 5 average rating, 80 reviews

Yurt in Afton

Mountain View Getaway Yurt

HaileyRating, 5 stars1 week ago

Our time staying at the yurt was above and beyond what we expected. The property and the yurt itself are so serene and enjoyable. Michelle is the most friendly host I have encountered, and talking with her about her goats brought so much joy! It is clear from the layout of the yurt to the care of the property all the way through the way they care for each and every guest and Michelle and her family truly love hosting. And that is something worth far more than five stars!

5 out of 5 average rating, 20 reviews

On the mountain, pet and child friendly

Mary KayRating, 5 stars3 weeks ago

Perfect cozy getaway with beautiful views. Great location within walking distance to golfing, Nature Center, pool, spa & food.

5 out of 5 average rating, 31 reviews

Buena Vista Panoramic Retreat: Million Dollar View

NicoleRating, 5 stars1 month ago

Our stay was fantastic! Absolutely beautiful place and location - as stated by others the views are spectacular. Super clean, very well appointed and comfortable. We will absolutely be back and are looking forward to it. The hosts were wonderful to work with!

Home in Wintergreen Resort

5 out of 5 average rating, 28 reviews

Luxury|Outdoor Lounge|Hot Tub|Fire Pit|Family&Pets

LauraRating, 5 stars4 days ago

Chris and his manager runs an excellent property. The property provides many thoughtful items to make your stay comfortable, enjoyable and homey. Only negative is HOAs rule that limits renters access to resort amenities.

Cabin in Wintergreen Resort

4.92 out of 5 average rating, 39 reviews

Serenity Cabin: Woodland Retreat

DonRating, 5 stars1 week ago

We used to spend a decent amount of time at Wintergreen but hadn’t in several years. This beautiful home was a wonderful welcome back. The location is quiet and surrounded by beautiful ferns and woods. The home is comfortably furnished and well equipped. There’s a large deck to help you enjoy the surroundings. The location is right off the Blue Ridge Parkway and the resort itself has several hiking trails. We had originally planned to stay elsewhere but that fell through. Andrew and Allison responded quickly and allowed us to book at the last minute. We are very glad it worked out the way it did!

Home in Wintergreen Resort

4.9 out of 5 average rating, 20 reviews

What a View! Hot Tub Fireplace Grill King Beds

ChristyRating, 5 stars3 weeks ago

Absolutely magical stay! This home was everything we hoped for and more. From the moment we arrived, we were struck by the beauty of the house itself—thoughtfully designed, impeccably clean, and full of cozy touches that made it feel like a true retreat. The views were absolutely breathtaking—waking up to the sight of the mountains and falling asleep to the peaceful sounds of the nearby brook made the experience unforgettable. Every amenity we could have needed was provided, from a fully stocked kitchen to plush linens and little extras that showed how much care went into creating this space. Whether we were relaxing indoors or enjoying the natural surroundings, it was pure peace and comfort. Thank you for sharing your beautiful home!