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Holiday rentals in Dripping Rock

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Top-rated holiday rentals in Dripping Rock

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Home in Roseland

4.88 out of 5 average rating, 116 reviews

Hiker’s paradise with NEW HOT TUB!

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!

Guest favourite

Cottage in Afton

4.99 out of 5 average rating, 161 reviews

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.

Guest favourite

Apartment in Wintergreen Resort

5.0 out of 5 average rating, 167 reviews

Wintergreen: Mountain View for Miles Sunset Vista

Welcome to Sunset Vista Villa! This beautifully appointed, 2 bedroom, 2 bath, first-floor-unit with second story views, is centrally located to all of the 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, Sunset Vista Villa will be sure to enhance your stay. Book today & come enjoy the Wintergreen Resort and Blue Ridge Mountains!

Guest favourite

Apartment in Wintergreen Resort

4.9 out of 5 average rating, 180 reviews

A True Mountain Getaway! Ski in/Ski out!

Located steps away from the top of the ski slopes at Wintergreen Resort. No snow? No problem! Enjoy the cool mountain breezes, hiking and climbing trails, mountain lakes with beaches, wineries, breweries and much much more. Restaurants and shopping within walking distance. Our place has a galley kitchen and small refrigerator, a large deck to enjoy a quiet dinner and has been newly decorated. There is a king sized bed and a smaller fold out sofa that could accommodate two small children.

Guest favourite

Cottage in Roseland

5.0 out of 5 average rating, 178 reviews

Blue Ridge Cottage - 3 Miles to Wintergreen

Our little piece of Blue Ridge Heaven is ready to share! Cozy - 2 bedrooms (one king, one queen), 1 bath, 956 square feet - well appointed in a terrific location! Beautiful mountain view from the 360 square foot, partially covered deck; fiber optic TV and wi-fi; South Fork of the Rockfish River out back. 3 miles from Wintergreen Resort, 1 mile from Devil's Backbone; Close to great hiking/biking, and many wineries, breweries, cideries, and distilleries (if you're into that kind of thing!)!

Guest favourite

Apartment in Wintergreen Resort

4.95 out of 5 average rating, 201 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.

Guest favourite

Cabin in Roseland

4.96 out of 5 average rating, 657 reviews

Cozy Mountain Cabin

Snuggled in the Blue Ridge. Secluded from the crowds. Experience your visit in an authentic log cabin. Perfect romantic getaway or personal retreat. Less than 2 miles to Devil's Backbone and Bold Rock. Minutes from the Appalachian Trail, Wintergreen 4-Season Resort, many breweries, wineries, cideries, restaurants, horseback riding, hiking trails, outdoor concerts, and antique shopping. Complimentary hot cocoa, tea, coffee, popcorn. High-speed internet, SMART TV. Air Conditioning.

Guest favourite

Cottage in Afton

4.9 out of 5 average rating, 485 reviews

Couples Getaway,heart of RT 151,stunning views

The Cottage is conveniently located along the Brew Ridge Trail. Sit on your patio and watch the sun set over Humpback rock and the Blue Ridge Mountains. Amazing location that’s set right in the middle of all the breweries. Spacious 6 acre farm with Route 151 road frontage. This handsome cottage is the perfect romantic get-a-way. Enjoy WiFi, air con, parking, self check-in and all the amenities you need to feel at home. Picturesque mountain views and beautifully landscaped grounds.

Guest favourite

Apartment in Roseland

4.94 out of 5 average rating, 202 reviews

Mountain Getaway - Unbeatable Views

One bedroom, one bath mountaintop condo featuring wood-burning fireplace, wrap-around deck, and amazing views. Located on the first floor with parking directly outside. Bedroom features a queen bed and TV. Only 1.5 miles to Mountain Inn and ski slopes. Unit is located in the High Ridge Place complex along Blue Ridge Drive at the Wintergreen Resort, although the address is Roseland, VA. A resort map can be found on the Wintergreen website. Address will be sent upon booking.

Guest favourite

Cabin in Vesuvius

4.97 out of 5 average rating, 166 reviews

Whimsical Creekside Cabin

Escape to our cabin in the Blue Ridge Mountains! Fall asleep to sounds of Little Mary’s Creek, enjoy your coffee on the wrap around deck, or delight in exploring your own 7 acres in the forest. Our cabin is a cheerful, clean cottage to come home to- or decide to spend your days on property splashing in the creek and sitting out by the fire pit. We invite you to embrace our simpler way of life where we wholeheartedly believe that life is to be enjoyed and not endured.

Guest favourite

Flat in Rockfish

4.99 out of 5 average rating, 160 reviews

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 the dog park, and picnic area it’s an ideal location.

Guest favourite

Cabin in Rockbridge Baths

4.97 out of 5 average rating, 271 reviews

Little Cabin in the Woods is quiet and secluded!

Enjoy our rustic, cozy, historic log cabin in the woods on 21 acres with two streams and a little meadow. The logs, from the 1800's, were reconfigured 17 years ago combining a rich history with high speed internet and modern amenities. Sink into the luscious bed with totally organic sheets, mattress topper, and pillows. Take a walk on the original wagon train road down to a stream or bath your senses in the majestic view of Jump Mountain from the meadow.

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Other great holiday rentals in Dripping Rock

Guest favourite

Cottage in Tyro

5.0 out of 5 average rating, 188 reviews

Bear Creek Inn

Guest favourite

Apartment in Wintergreen Resort

4.96 out of 5 average rating, 156 reviews

The Modern Mountain Condo

Guest favourite

Apartment in Wintergreen Resort

4.94 out of 5 average rating, 226 reviews

Cozy, clean mountain condo- King bed, dog friendly

Guest favourite

Yurt in Afton

5.0 out of 5 average rating, 813 reviews

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

Guest favourite

Apartment in Wintergreen Resort

4.99 out of 5 average rating, 116 reviews

Amazing Blue Ridge ski-front views with Wintermint

Guest favourite

Apartment in Roseland

4.94 out of 5 average rating, 36 reviews

Nature’s Haven 1 Bedroom Condo Wintergreen Resort

Guest favourite

Apartment in Wintergreen Resort

5.0 out of 5 average rating, 34 reviews

Enjoy Spring with the Best Views at Wintergreen !

Guest favourite

Flat in Wintergreen Resort

5.0 out of 5 average rating, 33 reviews

Mountain View Nest

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