Vacation rentals in Dripping Rock

4.99 out of 5 average rating, 182 reviews

Cottage in Afton

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

4.96 out of 5 average rating, 701 reviews

A group of ducks rests on the ground inside a fenced area, surrounded by a natural setting. Some ducks are white, while others display different colors and patterns. A small enclosure is visible in the background, housing a rabbit, with a wooden top providing shelter.

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, 582 reviews

The exterior of the tiny house is illuminated by string lights, creating a warm ambiance at night. A grassy area is dotted with colorful adirondack chairs. Natural stones are arranged throughout the yard, enhancing the outdoor setting.

Guesthouse 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.

Superhost

A spacious porch is surrounded by wooden railings, offering views of the forest with trees showcasing fall colors. A wooden staircase leads to the upper level, and leaves are scattered across the floor, suggesting a seasonal atmosphere.

Home in Roseland

4.88 out of 5 average rating, 143 reviews

Summer Time and the Livin is Easy! Fall is coming!

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!

4.99 out of 5 average rating, 235 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.

4.98 out of 5 average rating, 116 reviews

The living area features a stone fireplace with an electric insert, complemented by a large flat-screen TV mounted above. A mix of comfortable seating, including leather and fabric sofas, surrounds a wooden coffee table. Warm wood accents and camp-themed decor adorn the walls, creating a cozy atmosphere.

Chalet in Afton

Elk Mountain Overlook: Breathtaking Views

Mountaintop overlook with jaw dropping views and camp themed interior design. Perched upon Elk Mountain just off the Blue Ridge Parkway this petite chalet is under 30 min from Charlottesville, 10 min to 151 vineyards/breweries/cideries, and 10 min to Waynesboro. Relax in this natural retreat featuring 2 king bedrooms, 2 person soaker tub, double headed shower, and ample kitchen w/many extras. Take in the views from the large deck, firepit, under porch swing, or mountainside adirondack chairs.

5 out of 5 average rating, 917 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, 276 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.

A person is seen walking towards a scenic view where mountains rise above a sea of clouds. Lush green foliage frames the foreground, adding to the tranquil atmosphere of the landscape under a clear blue sky.

4.94 out of 5 average rating, 229 reviews

Eight Minute Walk to Everything

This one-bedroom, one-bath condo is centrally located. Ski check-in, restaurants, the mountaintop provisions market, and the Mountain Inn and conference center are all within an 8 minute walk. It's a one-story, downstairs unit that includes a back porch with just a few steps down to the ground. Perfect for taking the dog outside in the pet-friendly space. Full kitchen and dishes, wood-burning fireplace, balcony, and all towels and linens are provided for your convenience. Sleeps 3.

4.99 out of 5 average rating, 181 reviews

Treehouse in Verona

The Laurel Hill Treehouse

Fully immerse yourself in nature in this serene Scandinavian-inspired woodland retreat, ideal for a couple's getaway. The treehouse is perfectly nestled amongst the trees, offering a chance to unwind while enjoying the beautiful views of nature. Just imagine yourself relaxing on the wrap around porch, soaking in the hot tub, cooling off in the creek, & cozying up to a crackling fire. We invite you to unwind, reconnect with nature & create cherished memories in this tranquil hideaway.

5 out of 5 average rating, 238 reviews

Sunset Vista Mountain Views “Skies for Miles”

Welcome to Sunset Vista Villa, where you enjoy, “Skies for Miles.” This beautiful, 2 bedroom, 2 bath, first-floor-unit with second story mountain views, is near all amenities the Wintergreen Resort has to offer. It comfortably sleeps five and with its western vistas, sunsets are a thing to behold! Whether you spend your days hiking, skiing or enjoying the wineries and breweries, SVV will enhance your stay. Book today & come enjoy the Wintergreen Resort and Blue Ridge Mountains!

A sign marking the entrance to Laurelwood is framed by tall trees and lush greenery. Colorful flowers are arranged around the base of the sign, adding a touch of nature to the setting. The area appears well-maintained, indicating a welcoming environment for guests.

4.96 out of 5 average rating, 145 reviews

1 bedroom condo, hiking, breweries, wineries

Enjoy the mountains in the spring & summer enjoy hiking or a swim in the heapool! 1BR 1BA centrally located in Wintergreen 5 minute walk to Wintergreen resort Close to many hiking trails Enjoy the many breweries & wineries in the area Mountaintop Market is across the street 1 Bedroom 1 Bath & New queen sleeper sofa Stocked kitchen, cookware, spices & cooking oils Premium coffee & assorted tea Private furnished patio Wood burning fireplace, all you need for a quiet getaway

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Other great vacation rentals in Dripping Rock

5 out of 5 average rating, 17 reviews

Home in Crozet

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

RaymondRating, 5 stars2 days ago

My stay in Crozet was absolutely exceptional thanks to this beautiful property. The home features stunning minimalistic interior design that matched the listing photos perfectly, while the spectacular views and adjacent lavender farm create a truly unique and peaceful atmosphere. The property seamlessly integrates with its natural surroundings, offering a tranquil retreat that feels both luxurious and authentically connected to the Virginia countryside. I highly recommend this home to anyone seeking a rejuvenating getaway—it delivers an outstanding experience that will leave you thoroughly refreshed.

A wooden deck connects to a pathway lined with trees displaying vibrant autumn foliage. Natural light filters through the leaves, casting gentle shadows on the steps leading upwards, inviting exploration of the surrounding forest.

5 out of 5 average rating, 22 reviews

On the mountain, pet and child friendly

ErikaRating, 5 stars1 week ago

We had a fantastic stay! Would love to book again. The space has a great lay-out, comfortable rooms, and the deck has a great private view overlooking the golf course. It’s a great location by overlooks, trails, and restaurants. The hosts were amazing and friendly, and very responsive . Thanks again for a great trip!

Cabin in Wintergreen Resort

5 out of 5 average rating, 67 reviews

Hot Tub & Views | Mid Century Modern Wonder

JohannaRating, 5 stars1 week ago

We had a fantastic stay at this cabin! The place was spotless, well-maintained, and located in a perfect spot—peaceful yet close to everything we needed. The hosts were incredibly responsive and kind, making the whole experience smooth and welcoming. Highly recommend for anyone looking for a comfortable and relaxing getaway!

4.98 out of 5 average rating, 82 reviews

An outdoor bathing area features a white clawfoot tub set upon a wooden deck, surrounded by natural greenery. Curtains drape elegantly alongside the tub, enhancing privacy. A small mat is placed in front of the tub, while wooden slats provide a rustic backdrop.

Yurt in Afton

Mountain View Getaway Yurt

HaileyRating, 5 stars3 weeks 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!

Villa in Wintergreen Resort

A spacious living area is highlighted by large floor-to-ceiling windows, offering views of the surrounding trees. A comfortable gray sofa and a round glass coffee table are present, along with a wooden dining table that seats six. An electric fireplace adds warmth to the space.

4.97 out of 5 average rating, 89 reviews

NO STEP ENTRY Wintergreen Mtn Home,HotTub,Sleeps10

SarahRating, 5 stars1 day ago

Ben’s place was lovely for our group! The living room is gorgeous, kitchen is well stocked, there is lots of bathrooms, and all the bedrooms were very cozy. The hot tub was also large and on a lovely patio. We enjoyed the fire pit and quiet surroundings on the deck as well.

Apartment in Wintergreen Resort

An inviting entryway is captured, featuring a sleek, glass front door that opens to a private outdoor area with greenery. A small wooden console table holds magazines and a decorative basket. A mirror reflects light, enhancing the space's openness and warmth.

5 out of 5 average rating, 12 reviews

3 Ridges 3 min walk to slopes,besides inn,King bed

AlexusRating, 5 stars4 weeks ago

Great stay! The place was super clean and easy to get into. A perfect spot for a week in mountain getaway. The host was super responsive and friendly. I highly recommend this stay!

The bright and modern kitchen features dark cabinetry and stainless steel appliances, complemented by a white countertop. A spacious bar with three wooden stools invites casual dining, while large windows provide scenic views of the surrounding landscape.

5 out of 5 average rating, 6 reviews

Overlook 180 degree views w/Peloton!

GaryRating, 5 stars1 month ago

We enjoyed our stay at the air key Airbnb. It is very nice and comfortable place that is well stocked and has a great view of the mountains in Valley. We will definitely stay here again. My only complaint through no fault of Airkey was the maintenance on the outside of the building with the lift beeping every 30 seconds got to be a little annoying. But once again, it was a great place to stay. Highly recommended.